{"transactions":[{"id":781369,"issuer":{"id":412,"kind":"organization","name":"FORRESTER RESEARCH, INC.","symbol":"FORR"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":false,"ten_percent_owner":false,"other":false}}],"security":"Common Stock","published_at":"2026-05-13T17:58:55.000Z","date":"2026-05-12","kind":"grant","planned":false,"acquired":true,"shares":8000,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"shares","element":"transactionShares","label":"F1","text":"The securities awarded on May 12, 2026 are in the form of Restricted Stock Units issued pursuant to the Forrester Research, Inc. Amended and Restated Equity Incentive Plan that entitle the reporting person, upon vesting, to receive one\nshare of common stock per Restricted Stock Unit. The Restricted Stock Units will vest and convert into common stock in four equal and consecutive installments. The first tranche will vest on September 1, 2026, with an equal number of\nshares vesting on each of December 1, 2026 and March 1, 2027, and the balance of the shares vesting on June 1, 2027."}],"balance_after":27305,"source":{"system":"sec-edgar","filing":"0001193125-26-221244","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1023313/000119312526221244/ownership.xml","form_type":"4"}},{"id":1126041,"issuer":{"id":412,"kind":"organization","name":"FORRESTER RESEARCH, INC.","symbol":"FORR"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":false,"ten_percent_owner":false,"other":false}}],"security":"Common Stock","published_at":"2025-06-03T18:55:29.000Z","date":"2025-06-02","kind":"grant","planned":false,"acquired":true,"shares":8000,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"shares","element":"transactionShares","label":"F1","text":"The securities awarded on June 2, 2025 are in the form of Restricted Stock Units issued pursuant to the Forrester Research, Inc. Amended and Restated Equity Incentive Plan that entitle the reporting person, upon vesting, to receive one\nshare of common stock per Restricted Stock Unit. The Restricted Stock Units will vest and convert into common stock in four equal and consecutive installments. The first tranche will vest on September 1, 2025, with an equal number of shares vesting on each of December 1, 2025 and March 1, 2026, and the balance of the shares vesting on June 1, 2026."}],"balance_after":19305,"source":{"system":"sec-edgar","filing":"0000950170-25-080798","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1023313/000095017025080798/ownership.xml","form_type":"4"}},{"id":1236781,"issuer":{"id":412,"kind":"organization","name":"FORRESTER RESEARCH, INC.","symbol":"FORR"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":false,"ten_percent_owner":false,"other":false}}],"security":"Common Stock","published_at":"2025-03-03T17:13:12.000Z","date":"2025-02-28","kind":"grant","planned":false,"acquired":true,"shares":4000,"price":10.9868,"value":43947.2,"ownership":{"direct":true},"footnotes":[{"field":"price","element":"transactionPricePerShare","label":"F1","text":"This transaction was executed in multiple trades at prices ranging from $10.90 to $11.08.  The price reported above reflects the weighted average sale price.  The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected."}],"balance_after":11305,"source":{"system":"sec-edgar","filing":"0000950170-25-030491","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1023313/000095017025030491/ownership.xml","form_type":"4"}},{"id":1441341,"issuer":{"id":412,"kind":"organization","name":"FORRESTER RESEARCH, INC.","symbol":"FORR"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":false,"ten_percent_owner":false,"other":false}}],"security":"Common Stock","published_at":"2024-08-05T16:58:08.000Z","date":"2024-08-01","kind":"grant","planned":false,"acquired":true,"shares":6305,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"shares","element":"transactionShares","label":"F1","text":"The securities awarded on August 1, 2024 are in the form of Restricted Stock Units issued pursuant to the Forrester Research, Inc. Amended and Restated Equity Incentive Plan that entitle the reporting person, upon vesting, to receive one share of common stock per Restricted Stock Unit. The Restricted Stock Units will vest and convert into common stock in four equal and consecutive installments. The first tranche will vest on September 1, 2024, with an equal number of shares vesting on each of December 1, 2024 and March 1, 2025, and the balance of the shares vesting on June 1, 2025."}],"balance_after":7305,"source":{"system":"sec-edgar","filing":"0000950170-24-090547","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1023313/000095017024090547/ownership.xml","form_type":"4"}},{"id":1668291,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Option to Purchase Common Stock","published_at":"2024-01-29T22:30:45.000Z","date":"2024-01-26","kind":"disposition_to_issuer","planned":false,"acquired":false,"shares":427911,"ownership":{"direct":true},"footnotes":[{"field":"price","element":"transactionPricePerShare","label":"F4","text":"Under the Merger Agreement, at the Effective Time, each option to purchase Shares (a \"Company Option\") that was reported in this Form 4 was cancelled and converted into the right to receive an amount (without interest) in cash equal in value to (A) the total number of Shares subject to such Company Option multiplied by (B) the excess, if any, of the Per Share Price over the exercise price per Share underlying such Company Option."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F4","text":"Under the Merger Agreement, at the Effective Time, each option to purchase Shares (a \"Company Option\") that was reported in this Form 4 was cancelled and converted into the right to receive an amount (without interest) in cash equal in value to (A) the total number of Shares subject to such Company Option multiplied by (B) the excess, if any, of the Per Share Price over the exercise price per Share underlying such Company Option."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F4","text":"Under the Merger Agreement, at the Effective Time, each option to purchase Shares (a \"Company Option\") that was reported in this Form 4 was cancelled and converted into the right to receive an amount (without interest) in cash equal in value to (A) the total number of Shares subject to such Company Option multiplied by (B) the excess, if any, of the Per Share Price over the exercise price per Share underlying such Company Option."}],"balance_after":0,"derivative":{"exercise_price":5.67,"underlying":"Common Stock","underlying_shares":427911},"source":{"system":"sec-edgar","filing":"0000950170-24-008415","document":"ownership.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024008415/ownership.xml","form_type":"4"}},{"id":1668290,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2024-01-29T22:30:45.000Z","date":"2024-01-26","kind":"disposition_to_issuer","planned":false,"acquired":false,"shares":249352,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F2","text":"Each Company restricted stock unit (\"Company RSUs\") represented a contingent right to receive one Share upon vesting of the Company RSU."},{"field":"price","element":"transactionPricePerShare","label":"F3","text":"Under the Merger Agreement, at the Effective Time, each Company RSU reported in this Form 4 was cancelled and converted into the contingent right to receive from Parent or the Company a converted cash award (a \"Converted Cash Award\") with respect to an aggregate amount in cash equal in value to (A) the total number of Shares subject to such Company RSU immediately prior to the Effective Time multiplied by (B) the Per Share Price, which Converted Cash Award will remain subject to the same vesting terms and conditions of the corresponding Company RSU."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F3","text":"Under the Merger Agreement, at the Effective Time, each Company RSU reported in this Form 4 was cancelled and converted into the contingent right to receive from Parent or the Company a converted cash award (a \"Converted Cash Award\") with respect to an aggregate amount in cash equal in value to (A) the total number of Shares subject to such Company RSU immediately prior to the Effective Time multiplied by (B) the Per Share Price, which Converted Cash Award will remain subject to the same vesting terms and conditions of the corresponding Company RSU."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F3","text":"Under the Merger Agreement, at the Effective Time, each Company RSU reported in this Form 4 was cancelled and converted into the contingent right to receive from Parent or the Company a converted cash award (a \"Converted Cash Award\") with respect to an aggregate amount in cash equal in value to (A) the total number of Shares subject to such Company RSU immediately prior to the Effective Time multiplied by (B) the Per Share Price, which Converted Cash Award will remain subject to the same vesting terms and conditions of the corresponding Company RSU."}],"balance_after":0,"derivative":{"underlying":"Common Stock","underlying_shares":249352},"source":{"system":"sec-edgar","filing":"0000950170-24-008415","document":"ownership.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024008415/ownership.xml","form_type":"4"}},{"id":1668289,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2024-01-29T22:30:45.000Z","date":"2024-01-26","kind":"disposition_to_issuer","planned":false,"acquired":false,"shares":1332000,"price":23,"value":30636000.0,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"price","element":"transactionPricePerShare","label":"F1","text":"This Form 4 reports securities disposed of under the Agreement and Plan of Merger (the \"Merger Agreement\"), dated October 23, 2023, among EngageSmart, Inc. (the \"Company\"), Icefall Parent, Inc. (\"Parent\"), and Icefall Merger Sub, LLC (\"Merger Sub\"), under which Merger Sub was merged with and into the Company (the \"Merger\"), with the Company continuing as the surviving corporation in the Merger. At the effective time of the Merger (the \"Effective Time\"), each issued and outstanding share of common stock of the Company (\"Shares\") was cancelled and converted into the right to receive $23.00 in cash (the \"Per Share Price\") without interest thereon."}],"balance_after":0,"source":{"system":"sec-edgar","filing":"0000950170-24-008415","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024008415/ownership.xml","form_type":"4"}},{"id":1668288,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2024-01-29T22:30:45.000Z","date":"2024-01-26","kind":"disposition_to_issuer","planned":false,"acquired":false,"shares":809877,"price":23,"value":18627171.0,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"price","element":"transactionPricePerShare","label":"F1","text":"This Form 4 reports securities disposed of under the Agreement and Plan of Merger (the \"Merger Agreement\"), dated October 23, 2023, among EngageSmart, Inc. (the \"Company\"), Icefall Parent, Inc. (\"Parent\"), and Icefall Merger Sub, LLC (\"Merger Sub\"), under which Merger Sub was merged with and into the Company (the \"Merger\"), with the Company continuing as the surviving corporation in the Merger. At the effective time of the Merger (the \"Effective Time\"), each issued and outstanding share of common stock of the Company (\"Shares\") was cancelled and converted into the right to receive $23.00 in cash (the \"Per Share Price\") without interest thereon."}],"balance_after":0,"source":{"system":"sec-edgar","filing":"0000950170-24-008415","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024008415/ownership.xml","form_type":"4"}},{"id":1668287,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2024-01-29T22:30:45.000Z","date":"2024-01-26","kind":"disposition_to_issuer","planned":false,"acquired":false,"shares":859710,"price":23,"value":19773330.0,"ownership":{"direct":true},"footnotes":[{"field":"price","element":"transactionPricePerShare","label":"F1","text":"This Form 4 reports securities disposed of under the Agreement and Plan of Merger (the \"Merger Agreement\"), dated October 23, 2023, among EngageSmart, Inc. (the \"Company\"), Icefall Parent, Inc. (\"Parent\"), and Icefall Merger Sub, LLC (\"Merger Sub\"), under which Merger Sub was merged with and into the Company (the \"Merger\"), with the Company continuing as the surviving corporation in the Merger. At the effective time of the Merger (the \"Effective Time\"), each issued and outstanding share of common stock of the Company (\"Shares\") was cancelled and converted into the right to receive $23.00 in cash (the \"Per Share Price\") without interest thereon."}],"balance_after":0,"source":{"system":"sec-edgar","filing":"0000950170-24-008415","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024008415/ownership.xml","form_type":"4"}},{"id":1693312,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2024-01-04T01:40:52.000Z","date":"2024-01-01","kind":"exercise","planned":false,"acquired":false,"shares":19377,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F2","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F4","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F4","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."}],"balance_after":232525,"derivative":{"underlying":"Common Stock","underlying_shares":19377},"source":{"system":"sec-edgar","filing":"0000950170-24-001408","document":"ownership.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":8,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024001408/ownership.xml","form_type":"4"}},{"id":1693311,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2024-01-04T01:40:52.000Z","date":"2024-01-01","kind":"exercise","planned":false,"acquired":false,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F2","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F3","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F3","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":16827,"derivative":{"underlying":"Common Stock","underlying_shares":2404},"source":{"system":"sec-edgar","filing":"0000950170-24-001408","document":"ownership.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":7,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024001408/ownership.xml","form_type":"4"}},{"id":1693310,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2024-01-04T01:40:52.000Z","date":"2024-01-01","kind":"tax_withholding","planned":false,"acquired":false,"shares":5938,"price":22.9,"value":135980.2,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of shares of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":859710,"source":{"system":"sec-edgar","filing":"0000950170-24-001408","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024001408/ownership.xml","form_type":"4"}},{"id":1693309,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2024-01-04T01:40:52.000Z","date":"2024-01-01","kind":"exercise","planned":false,"acquired":true,"shares":19377,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":865648,"source":{"system":"sec-edgar","filing":"0000950170-24-001408","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024001408/ownership.xml","form_type":"4"}},{"id":1693308,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2024-01-04T01:40:52.000Z","date":"2024-01-01","kind":"tax_withholding","planned":false,"acquired":false,"shares":833,"price":22.9,"value":19075.7,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of shares of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":846271,"source":{"system":"sec-edgar","filing":"0000950170-24-001408","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024001408/ownership.xml","form_type":"4"}},{"id":1693307,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2024-01-04T01:40:52.000Z","date":"2024-01-01","kind":"exercise","planned":false,"acquired":true,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":847104,"source":{"system":"sec-edgar","filing":"0000950170-24-001408","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017024001408/ownership.xml","form_type":"4"}},{"id":1767947,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2023-10-03T20:30:16.000Z","date":"2023-10-01","kind":"exercise","planned":false,"acquired":false,"shares":19377,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F2","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F4","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F4","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."}],"balance_after":251902,"derivative":{"underlying":"Common Stock","underlying_shares":19377},"source":{"system":"sec-edgar","filing":"0000950170-23-051559","document":"ownership.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":8,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023051559/ownership.xml","form_type":"4"}},{"id":1767946,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2023-10-03T20:30:16.000Z","date":"2023-10-01","kind":"exercise","planned":false,"acquired":false,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F2","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F3","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F3","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":19231,"derivative":{"underlying":"Common Stock","underlying_shares":2404},"source":{"system":"sec-edgar","filing":"0000950170-23-051559","document":"ownership.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":7,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023051559/ownership.xml","form_type":"4"}},{"id":1767945,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-10-03T20:30:16.000Z","date":"2023-10-01","kind":"tax_withholding","planned":false,"acquired":false,"shares":8594,"price":17.99,"value":154606.06,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of shares of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":844700,"source":{"system":"sec-edgar","filing":"0000950170-23-051559","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023051559/ownership.xml","form_type":"4"}},{"id":1767944,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-10-03T20:30:16.000Z","date":"2023-10-01","kind":"exercise","planned":false,"acquired":true,"shares":19377,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":853294,"source":{"system":"sec-edgar","filing":"0000950170-23-051559","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023051559/ownership.xml","form_type":"4"}},{"id":1767943,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-10-03T20:30:16.000Z","date":"2023-10-01","kind":"tax_withholding","planned":false,"acquired":false,"shares":1067,"price":17.99,"value":19195.33,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of shares of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":833917,"source":{"system":"sec-edgar","filing":"0000950170-23-051559","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023051559/ownership.xml","form_type":"4"}},{"id":1767942,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-10-03T20:30:16.000Z","date":"2023-10-01","kind":"exercise","planned":false,"acquired":true,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":834984,"source":{"system":"sec-edgar","filing":"0000950170-23-051559","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023051559/ownership.xml","form_type":"4"}},{"id":1829689,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Stock Option","published_at":"2023-07-15T00:47:13.000Z","date":"2023-07-12","kind":"exercise","planned":true,"acquired":false,"shares":22089,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_date","element":"exerciseDate","label":"F5","text":"The stock option vested and became exercisable with respect to 25% of the underlying shares on February 2, 2022 and will vest with respect to the remaining shares in twelve equal quarterly installments beginning on April 1, 2022, subject to the Reporting Person's continued service to the Issuer through each vesting date."}],"balance_after":427911,"derivative":{"exercise_price":5.67,"expiration_date":"2031-02-01","underlying":"Common Stock","underlying_shares":22089},"source":{"system":"sec-edgar","filing":"0000950170-23-033088","document":"ownership.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023033088/ownership.xml","form_type":"4"}},{"id":1829688,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-15T00:47:13.000Z","date":"2023-07-12","kind":"exercise","planned":true,"acquired":true,"shares":22089,"price":5.67,"value":125244.63,"ownership":{"direct":true},"balance_after":832580,"source":{"system":"sec-edgar","filing":"0000950170-23-033088","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023033088/ownership.xml","form_type":"4"}},{"id":1829687,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-15T00:47:13.000Z","date":"2023-07-05","kind":"sale","planned":true,"acquired":false,"shares":28000,"price":18.53,"value":518840.0,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F4","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.25 to $18.75. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1332000,"source":{"system":"sec-edgar","filing":"0000950170-23-033088","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023033088/ownership.xml","form_type":"4"}},{"id":1829686,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-15T00:47:13.000Z","date":"2023-07-05","kind":"sale","planned":true,"acquired":false,"shares":28000,"price":18.53,"value":518840.0,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F3","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.25 to $18.75. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":809877,"source":{"system":"sec-edgar","filing":"0000950170-23-033088","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023033088/ownership.xml","form_type":"4"}},{"id":1829685,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-15T00:47:13.000Z","date":"2023-07-05","kind":"sale","planned":true,"acquired":false,"shares":28000,"price":18.53,"value":518840.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F2","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.25 to $18.75. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":810491,"source":{"system":"sec-edgar","filing":"0000950170-23-033088","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023033088/ownership.xml","form_type":"4"}},{"id":1834170,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2023-07-07T01:39:06.000Z","date":"2023-07-01","kind":"exercise","planned":true,"acquired":false,"shares":19377,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F6","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F8","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F8","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."}],"balance_after":271279,"derivative":{"underlying":"Common Stock","underlying_shares":19377},"source":{"system":"sec-edgar","filing":"0000950170-23-032120","document":"ownership.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":9,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023032120/ownership.xml","form_type":"4"}},{"id":1834169,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2023-07-07T01:39:06.000Z","date":"2023-07-01","kind":"exercise","planned":true,"acquired":false,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F6","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F7","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F7","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":21635,"derivative":{"underlying":"Common Stock","underlying_shares":2404},"source":{"system":"sec-edgar","filing":"0000950170-23-032120","document":"ownership.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":8,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023032120/ownership.xml","form_type":"4"}},{"id":1834168,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-07T01:39:06.000Z","date":"2023-07-03","kind":"sale","planned":true,"acquired":false,"shares":14000,"price":18.67,"value":261380.0,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trus"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F5","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.49 to $18.99. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1360000,"source":{"system":"sec-edgar","filing":"0000950170-23-032120","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":7,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023032120/ownership.xml","form_type":"4"}},{"id":1834167,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-07T01:39:06.000Z","date":"2023-07-03","kind":"sale","planned":true,"acquired":false,"shares":14000,"price":18.67,"value":261380.0,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of shares of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."},{"field":"price","element":"transactionPricePerShare","label":"F4","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.49 to $18.99. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":837877,"source":{"system":"sec-edgar","filing":"0000950170-23-032120","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":6,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023032120/ownership.xml","form_type":"4"}},{"id":1834166,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-07T01:39:06.000Z","date":"2023-07-03","kind":"sale","planned":true,"acquired":false,"shares":14000,"price":18.67,"value":261380.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F3","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.49 to $18.99. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":838491,"source":{"system":"sec-edgar","filing":"0000950170-23-032120","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023032120/ownership.xml","form_type":"4"}},{"id":1834165,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-07T01:39:06.000Z","date":"2023-07-01","kind":"tax_withholding","planned":true,"acquired":false,"shares":7509,"price":19.09,"value":143346.81,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of shares of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":852491,"source":{"system":"sec-edgar","filing":"0000950170-23-032120","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023032120/ownership.xml","form_type":"4"}},{"id":1834164,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-07T01:39:06.000Z","date":"2023-07-01","kind":"exercise","planned":true,"acquired":true,"shares":19377,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":860000,"source":{"system":"sec-edgar","filing":"0000950170-23-032120","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023032120/ownership.xml","form_type":"4"}},{"id":1834163,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-07T01:39:06.000Z","date":"2023-07-01","kind":"tax_withholding","planned":true,"acquired":false,"shares":706,"price":19.09,"value":13477.54,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of shares of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":840623,"source":{"system":"sec-edgar","filing":"0000950170-23-032120","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023032120/ownership.xml","form_type":"4"}},{"id":1834162,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-07-07T01:39:06.000Z","date":"2023-07-01","kind":"exercise","planned":true,"acquired":true,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":841329,"source":{"system":"sec-edgar","filing":"0000950170-23-032120","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000095017023032120/ownership.xml","form_type":"4"}},{"id":1923898,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-07T01:06:39.000Z","date":"2023-04-05","kind":"sale","planned":true,"acquired":false,"shares":166,"price":18.07,"value":2999.62,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F10","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.88 to $18.17. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1374000,"source":{"system":"sec-edgar","filing":"0000899243-23-010942","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":9,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010942/doc4.xml","form_type":"4"}},{"id":1923897,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-07T01:06:39.000Z","date":"2023-04-05","kind":"sale","planned":true,"acquired":false,"shares":13834,"price":17.24,"value":238498.16,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F9","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.88 to $17.83. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1374166,"source":{"system":"sec-edgar","filing":"0000899243-23-010942","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":8,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010942/doc4.xml","form_type":"4"}},{"id":1923896,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-07T01:06:39.000Z","date":"2023-04-05","kind":"sale","planned":true,"acquired":false,"shares":167,"price":18.07,"value":3017.69,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F8","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.88 to $18.17. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":851877,"source":{"system":"sec-edgar","filing":"0000899243-23-010942","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":7,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010942/doc4.xml","form_type":"4"}},{"id":1923895,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-07T01:06:39.000Z","date":"2023-04-05","kind":"sale","planned":true,"acquired":false,"shares":13833,"price":17.24,"value":238480.92,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F7","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.88 to $17.83. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":852044,"source":{"system":"sec-edgar","filing":"0000899243-23-010942","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":6,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010942/doc4.xml","form_type":"4"}},{"id":1923894,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-07T01:06:39.000Z","date":"2023-04-05","kind":"sale","planned":true,"acquired":false,"shares":167,"price":18.07,"value":3017.69,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F6","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.88 to $18.17. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":838925,"source":{"system":"sec-edgar","filing":"0000899243-23-010942","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010942/doc4.xml","form_type":"4"}},{"id":1923893,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-07T01:06:39.000Z","date":"2023-04-05","kind":"sale","planned":true,"acquired":false,"shares":13833,"price":17.24,"value":238480.92,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F5","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.88 to $17.83. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":839092,"source":{"system":"sec-edgar","filing":"0000899243-23-010942","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010942/doc4.xml","form_type":"4"}},{"id":1923892,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-07T01:06:39.000Z","date":"2023-04-04","kind":"sale","planned":true,"acquired":false,"shares":14000,"price":18.27,"value":255780.0,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F4","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.05 to $18.84. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1388000,"source":{"system":"sec-edgar","filing":"0000899243-23-010942","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010942/doc4.xml","form_type":"4"}},{"id":1923891,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-07T01:06:39.000Z","date":"2023-04-04","kind":"sale","planned":true,"acquired":false,"shares":14000,"price":18.27,"value":255780.0,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F3","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.05 to $18.84. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":865877,"source":{"system":"sec-edgar","filing":"0000899243-23-010942","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010942/doc4.xml","form_type":"4"}},{"id":1923890,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-07T01:06:39.000Z","date":"2023-04-04","kind":"sale","planned":true,"acquired":false,"shares":14000,"price":18.27,"value":255780.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F2","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.05 to $18.84. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":852925,"source":{"system":"sec-edgar","filing":"0000899243-23-010942","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010942/doc4.xml","form_type":"4"}},{"id":1928980,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2023-04-05T01:51:11.000Z","date":"2023-04-01","kind":"exercise","planned":true,"acquired":false,"shares":19377,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F9","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F11","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F11","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."}],"balance_after":290656,"derivative":{"underlying":"Common Stock","underlying_shares":19377},"source":{"system":"sec-edgar","filing":"0000899243-23-010611","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":9,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010611/doc4.xml","form_type":"4"}},{"id":1928979,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2023-04-05T01:51:11.000Z","date":"2023-04-01","kind":"exercise","planned":true,"acquired":false,"shares":2403,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F9","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F10","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F10","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":24039,"derivative":{"underlying":"Common Stock","underlying_shares":2403},"source":{"system":"sec-edgar","filing":"0000899243-23-010611","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":8,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010611/doc4.xml","form_type":"4"}},{"id":1928978,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-05T01:51:11.000Z","date":"2023-04-03","kind":"sale","planned":true,"acquired":false,"shares":14000,"price":18.88,"value":264320.0,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F7","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F8","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.72 to $19.06. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1402000,"source":{"system":"sec-edgar","filing":"0000899243-23-010611","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":7,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010611/doc4.xml","form_type":"4"}},{"id":1928977,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-05T01:51:11.000Z","date":"2023-04-03","kind":"sale","planned":true,"acquired":false,"shares":14000,"price":18.88,"value":264320.0,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor\nRetained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F5","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F6","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.73 to $19.06. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":879877,"source":{"system":"sec-edgar","filing":"0000899243-23-010611","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":6,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010611/doc4.xml","form_type":"4"}},{"id":1928976,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-05T01:51:11.000Z","date":"2023-04-03","kind":"sale","planned":true,"acquired":false,"shares":14000,"price":18.88,"value":264320.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F3","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022."},{"field":"price","element":"transactionPricePerShare","label":"F4","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.71 to $19.06. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":866925,"source":{"system":"sec-edgar","filing":"0000899243-23-010611","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010611/doc4.xml","form_type":"4"}},{"id":1928975,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-05T01:51:11.000Z","date":"2023-04-01","kind":"tax_withholding","planned":true,"acquired":false,"shares":5688,"price":19.25,"value":109494.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":880925,"source":{"system":"sec-edgar","filing":"0000899243-23-010611","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010611/doc4.xml","form_type":"4"}},{"id":1928974,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-05T01:51:11.000Z","date":"2023-04-01","kind":"exercise","planned":true,"acquired":true,"shares":19377,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":886613,"source":{"system":"sec-edgar","filing":"0000899243-23-010611","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010611/doc4.xml","form_type":"4"}},{"id":1928973,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-05T01:51:11.000Z","date":"2023-04-01","kind":"tax_withholding","planned":true,"acquired":false,"shares":706,"price":19.25,"value":13590.5,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":867236,"source":{"system":"sec-edgar","filing":"0000899243-23-010611","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010611/doc4.xml","form_type":"4"}},{"id":1928972,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-04-05T01:51:11.000Z","date":"2023-04-01","kind":"exercise","planned":true,"acquired":true,"shares":2403,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"balance_after","element":"sharesOwnedFollowingTransaction","label":"F1","text":"Includes 45,101 shares previously held through the Robert P. Bennett 2020 Grantor Retained Annuity Trust, of which the Reporting Person serves as the sole trustee, which were distributed to the Reporting Person on January 31, 2023 and are now owned directly by the Reporting Person."}],"balance_after":867942,"source":{"system":"sec-edgar","filing":"0000899243-23-010611","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323010611/doc4.xml","form_type":"4"}},{"id":1966397,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-03-07T22:54:30.000Z","date":"2023-03-07","kind":"sale","acquired":false,"shares":34892,"price":18.1925,"value":634772.71,"ownership":{"direct":true},"footnotes":[{"field":"price","element":"transactionPricePerShare","label":"F1","text":"This amount represents a public offering price of $19.00 per share of common stock of EngageSmart, Inc. (the \"Common Stock\"), less an underwriting discount of $0.8075 per share for shares sold in an underwritten public offering."}],"balance_after":820438,"source":{"system":"sec-edgar","filing":"0000899243-23-007383","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323007383/doc4.xml","form_type":"4"}},{"id":1966396,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-03-07T22:54:30.000Z","date":"2023-03-03","kind":"sale","acquired":false,"shares":230433,"price":18.1925,"value":4192152.3525,"ownership":{"direct":true},"footnotes":[{"field":"price","element":"transactionPricePerShare","label":"F1","text":"This amount represents a public offering price of $19.00 per share of common stock of EngageSmart, Inc. (the \"Common Stock\"), less an underwriting discount of $0.8075 per share for shares sold in an underwritten public offering."}],"balance_after":855330,"source":{"system":"sec-edgar","filing":"0000899243-23-007383","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323007383/doc4.xml","form_type":"4"}},{"id":2028856,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2023-02-08T01:22:17.000Z","date":"2023-02-03","kind":"grant","acquired":true,"shares":310033,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F1","text":"Each restricted stock unit (\"RSU\") represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F2","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F2","text":"The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date."}],"balance_after":310033,"derivative":{"underlying":"Common Stock","underlying_shares":310033},"source":{"system":"sec-edgar","filing":"0000899243-23-004253","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323004253/doc4.xml","form_type":"4"}},{"id":2068638,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2023-01-05T02:19:05.000Z","date":"2023-01-01","kind":"exercise","acquired":false,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F9","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F10","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F10","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":26442,"derivative":{"underlying":"Common Stock","underlying_shares":2404},"source":{"system":"sec-edgar","filing":"0000899243-23-000749","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":9,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323000749/doc4.xml","form_type":"4"}},{"id":2068637,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-01-05T02:19:05.000Z","date":"2023-01-04","kind":"sale","acquired":false,"shares":14000,"price":17.51,"value":245140.0,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F8","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.29 to $17.92. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1416000,"source":{"system":"sec-edgar","filing":"0000899243-23-000749","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":8,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323000749/doc4.xml","form_type":"4"}},{"id":2068636,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-01-05T02:19:05.000Z","date":"2023-01-04","kind":"sale","acquired":false,"shares":14000,"price":17.51,"value":245140.0,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F7","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.29 to $17.92. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":938978,"source":{"system":"sec-edgar","filing":"0000899243-23-000749","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":7,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323000749/doc4.xml","form_type":"4"}},{"id":2068635,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-01-05T02:19:05.000Z","date":"2023-01-04","kind":"sale","acquired":false,"shares":14000,"price":17.51,"value":245140.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F6","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.29 to $17.92. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1085763,"source":{"system":"sec-edgar","filing":"0000899243-23-000749","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":6,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323000749/doc4.xml","form_type":"4"}},{"id":2068634,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-01-05T02:19:05.000Z","date":"2023-01-03","kind":"sale","acquired":false,"shares":28000,"price":17.67,"value":494760.0,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F5","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.54 to $17.99. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1430000,"source":{"system":"sec-edgar","filing":"0000899243-23-000749","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323000749/doc4.xml","form_type":"4"}},{"id":2068633,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-01-05T02:19:05.000Z","date":"2023-01-03","kind":"sale","acquired":false,"shares":28000,"price":17.67,"value":494760.0,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F4","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.55 to $18.00. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":952978,"source":{"system":"sec-edgar","filing":"0000899243-23-000749","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323000749/doc4.xml","form_type":"4"}},{"id":2068632,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-01-05T02:19:05.000Z","date":"2023-01-03","kind":"sale","acquired":false,"shares":28000,"price":17.67,"value":494760.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F3","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.54 to $17.99. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1099763,"source":{"system":"sec-edgar","filing":"0000899243-23-000749","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323000749/doc4.xml","form_type":"4"}},{"id":2068631,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-01-05T02:19:05.000Z","date":"2023-01-01","kind":"tax_withholding","acquired":false,"shares":833,"price":17.6,"value":14660.8,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":1127763,"source":{"system":"sec-edgar","filing":"0000899243-23-000749","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323000749/doc4.xml","form_type":"4"}},{"id":2068630,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2023-01-05T02:19:05.000Z","date":"2023-01-01","kind":"exercise","acquired":false,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":1128596,"source":{"system":"sec-edgar","filing":"0000899243-23-000749","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924323000749/doc4.xml","form_type":"4"}},{"id":2138470,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-12","kind":"sale","acquired":false,"shares":14000,"price":19.53,"value":273420.0,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F10","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.96 to $19.84. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote"}],"balance_after":1458000,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":15,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138469,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-12","kind":"sale","acquired":false,"shares":14000,"price":19.53,"value":273420.0,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F10","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.96 to $19.84. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote"}],"balance_after":980978,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":14,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138468,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-12","kind":"sale","acquired":false,"shares":14000,"price":19.53,"value":273420.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F10","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.96 to $19.84. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote"}],"balance_after":1126192,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":13,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138467,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-11","kind":"sale","acquired":false,"shares":333,"price":20.21,"value":6729.93,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F9","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $19.99 to $20.33. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1472000,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":12,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138466,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-11","kind":"sale","acquired":false,"shares":13667,"price":19.45,"value":265823.15,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F8","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.96 to $19.93. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1472333,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":11,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138465,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-11","kind":"sale","acquired":false,"shares":333,"price":20.21,"value":6729.93,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F9","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $19.99 to $20.33. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":994978,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":10,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138464,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-11","kind":"sale","acquired":false,"shares":13667,"price":19.45,"value":265823.15,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F8","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.96 to $19.93. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":995311,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":9,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138463,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-11","kind":"sale","acquired":false,"shares":334,"price":20.21,"value":6750.14,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F7","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $19.99 to $20.33. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1140192,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":8,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138462,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-11","kind":"sale","acquired":false,"shares":13666,"price":19.45,"value":265803.7,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F6","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.96 to $19.93. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1140526,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":7,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138461,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-10","kind":"sale","acquired":false,"shares":733,"price":21.39,"value":15678.87,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F5","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $21.22 to $21.69. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1486000,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":6,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138460,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-10","kind":"sale","acquired":false,"shares":13267,"price":20.5,"value":271973.5,"ownership":{"direct":false,"nature":"The Bennett Family 2020 Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F4","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $20.20 to $21.19. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1486733,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138459,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-10","kind":"sale","acquired":false,"shares":733,"price":21.39,"value":15678.87,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F5","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $21.22 to $21.69. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1008978,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138458,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-10","kind":"sale","acquired":false,"shares":13267,"price":20.5,"value":271973.5,"ownership":{"direct":false,"nature":"The Robert P. Bennett 2020 Grantor Retained Annuity Trust"},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F4","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $20.20 to $21.19. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1009711,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138457,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-10","kind":"sale","acquired":false,"shares":734,"price":20.39,"value":14966.26,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F3","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $21.22 to $21.69. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1154192,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2138456,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-13T01:30:59.000Z","date":"2022-10-10","kind":"sale","acquired":false,"shares":13266,"price":20.5,"value":271953.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan."},{"field":"price","element":"transactionPricePerShare","label":"F2","text":"The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $20.20 to $21.19. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote."}],"balance_after":1154926,"source":{"system":"sec-edgar","filing":"0000899243-22-033526","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322033526/doc4.xml","form_type":"4"}},{"id":2145106,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2022-10-05T00:27:18.000Z","date":"2022-10-01","kind":"exercise","acquired":false,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F3","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F4","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F4","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":28846,"derivative":{"underlying":"Common Stock","underlying_shares":2404},"source":{"system":"sec-edgar","filing":"0000899243-22-032810","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322032810/doc4.xml","form_type":"4"}},{"id":2145105,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-05T00:27:18.000Z","date":"2022-10-01","kind":"tax_withholding","acquired":false,"shares":1067,"price":20.69,"value":22076.23,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":1168192,"source":{"system":"sec-edgar","filing":"0000899243-22-032810","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322032810/doc4.xml","form_type":"4"}},{"id":2145104,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-10-05T00:27:18.000Z","date":"2022-10-01","kind":"exercise","acquired":true,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":1169259,"source":{"system":"sec-edgar","filing":"0000899243-22-032810","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322032810/doc4.xml","form_type":"4"}},{"id":2212304,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2022-07-06T22:12:37.000Z","date":"2022-04-01","kind":"exercise","acquired":false,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F4","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F5","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F5","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":31250,"derivative":{"underlying":"Common Stock","underlying_shares":2404},"source":{"system":"sec-edgar","filing":"0000899243-22-025467","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322025467/doc4.xml","form_type":"4"}},{"id":2212303,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-07-06T22:12:37.000Z","date":"2022-07-01","kind":"tax_withholding","acquired":false,"shares":1067,"price":16.4,"value":17498.8,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":1166855,"source":{"system":"sec-edgar","filing":"0000899243-22-025467","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322025467/doc4.xml","form_type":"4"}},{"id":2212302,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-07-06T22:12:37.000Z","date":"2022-07-01","kind":"exercise","acquired":true,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"balance_after","element":"sharesOwnedFollowingTransaction","label":"F1","text":"Includes 27,022 shares of common stock received as annuity payment from The Robert P. Bennett 2020 Grantor Retained Annuity Trust, of which the Reporting Person serves as the sole trustee."}],"balance_after":1167922,"source":{"system":"sec-edgar","filing":"0000899243-22-025467","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322025467/doc4.xml","form_type":"4"}},{"id":2305028,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2022-04-06T01:08:58.000Z","date":"2022-04-01","kind":"exercise","acquired":false,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F3","text":"Each RSU represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F4","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F4","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":33654,"derivative":{"underlying":"Common Stock","underlying_shares":2404},"source":{"system":"sec-edgar","filing":"0000899243-22-013952","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322013952/doc4.xml","form_type":"4"}},{"id":2305027,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-04-06T01:08:58.000Z","date":"2022-04-01","kind":"tax_withholding","acquired":false,"shares":1067,"price":22.06,"value":23538.02,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units (\"RSUs\")."}],"balance_after":1138496,"source":{"system":"sec-edgar","filing":"0000899243-22-013952","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322013952/doc4.xml","form_type":"4"}},{"id":2305026,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-04-06T01:08:58.000Z","date":"2022-04-01","kind":"exercise","acquired":true,"shares":2404,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":1139563,"source":{"system":"sec-edgar","filing":"0000899243-22-013952","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322013952/doc4.xml","form_type":"4"}},{"id":2315560,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Stock Option","published_at":"2022-03-29T22:58:49.000Z","date":"2022-02-11","kind":"exercise","acquired":true,"shares":150000,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_date","element":"exerciseDate","label":"F6","text":"The stock option vested and became exercisable with respect to 25% of the underlying shares on February 2, 2022 and will vest with respect to the remaining shares in twelve equal quarterly installments beginning on April 1, 2022, subject to the Reporting Person's continued service to the Issuer through each vesting date."}],"balance_after":450000,"derivative":{"exercise_price":5.67,"expiration_date":"2031-02-01","underlying":"Common Stock","underlying_shares":150000},"source":{"system":"sec-edgar","filing":"0000899243-22-012709","document":"doc4a.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":6,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322012709/doc4a.xml","form_type":"4/A","original_submission_date":"2022-02-15"}},{"id":2315559,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2022-03-29T22:58:49.000Z","date":"2022-01-01","kind":"exercise","acquired":false,"shares":2403,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F2","text":"Each restricted stock unit (\"RSU\") represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F5","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F5","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":36058,"derivative":{"underlying":"Common Stock","underlying_shares":2403},"source":{"system":"sec-edgar","filing":"0000899243-22-012709","document":"doc4a.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322012709/doc4a.xml","form_type":"4/A","original_submission_date":"2022-02-15"}},{"id":2315558,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-03-29T22:58:49.000Z","date":"2022-02-11","kind":"exercise","acquired":true,"shares":150000,"price":5.67,"value":850500.0,"ownership":{"direct":true},"footnotes":[{"field":"balance_after","element":"sharesOwnedFollowingTransaction","label":"F3","text":"The Original Form 4 inadvertently incorrectly stated the total number of shares of common stock directly beneficially owned by the Reporting Person. This amendment is being filed to correct the total number of shares of common stock directly beneficially owned by the Reporting Person."}],"balance_after":1137159,"source":{"system":"sec-edgar","filing":"0000899243-22-012709","document":"doc4a.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322012709/doc4a.xml","form_type":"4/A","original_submission_date":"2022-02-15"}},{"id":2315557,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-03-29T22:58:49.000Z","date":"2022-01-01","kind":"tax_withholding","acquired":false,"shares":833,"price":24.12,"value":20091.96,"ownership":{"direct":true},"balance_after":987159,"source":{"system":"sec-edgar","filing":"0000899243-22-012709","document":"doc4a.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322012709/doc4a.xml","form_type":"4/A","original_submission_date":"2022-02-15"}},{"id":2315556,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-03-29T22:58:49.000Z","date":"2022-01-01","kind":"exercise","acquired":true,"shares":2403,"ownership":{"direct":true},"footnotes":[{"field":"date","element":"transactionDate","label":"F1","text":"On February 15, 2022, the Reporting Person filed a Form 4 (the \"Original Form 4\") which inadvertently indicated that the date of earliest transaction required to be reported was 02/11/2022. The correct date of earliest transaction required to be reported is 01/01/2022. This amendment is being filed to correct the date of the earliest transaction required to be reported."},{"field":"price","element":"transactionPricePerShare","label":"F2","text":"Each restricted stock unit (\"RSU\") represents a contingent right to receive one share of common stock."}],"balance_after":987992,"source":{"system":"sec-edgar","filing":"0000899243-22-012709","document":"doc4a.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322012709/doc4a.xml","form_type":"4/A","original_submission_date":"2022-02-15"}},{"id":2394799,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Stock Option","published_at":"2022-02-16T02:40:29.000Z","date":"2022-02-11","kind":"exercise","acquired":true,"shares":150000,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_date","element":"exerciseDate","label":"F4","text":"The stock option vested and became exercisable with respect to 25% of the underlying shares on February 2, 2022 and will vest with respect to the remaining shares in twelve equal quarterly installments beginning on April 1, 2022, subject to the Reporting Person's continued service to the Issuer through each vesting date."}],"balance_after":450000,"derivative":{"exercise_price":5.67,"expiration_date":"2031-02-01","underlying":"Common Stock","underlying_shares":150000},"source":{"system":"sec-edgar","filing":"0000899243-22-006554","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":6,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322006554/doc4.xml","form_type":"4"}},{"id":2394798,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Units","published_at":"2022-02-16T02:40:29.000Z","date":"2022-01-01","kind":"exercise","acquired":false,"shares":2403,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F1","text":"Each restricted stock unit (\"RSU\") represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F3","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F3","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":36058,"derivative":{"underlying":"Common Stock","underlying_shares":2403},"source":{"system":"sec-edgar","filing":"0000899243-22-006554","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322006554/doc4.xml","form_type":"4"}},{"id":2394797,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-02-16T02:40:29.000Z","date":"2022-02-11","kind":"exercise","acquired":true,"shares":150000,"price":5.67,"value":850500.0,"ownership":{"direct":true},"balance_after":1135589,"source":{"system":"sec-edgar","filing":"0000899243-22-006554","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322006554/doc4.xml","form_type":"4"}},{"id":2394796,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-02-16T02:40:29.000Z","date":"2022-01-01","kind":"tax_withholding","acquired":false,"shares":833,"price":24.12,"value":20091.96,"ownership":{"direct":true},"balance_after":987159,"source":{"system":"sec-edgar","filing":"0000899243-22-006554","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322006554/doc4.xml","form_type":"4"}},{"id":2394795,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2022-02-16T02:40:29.000Z","date":"2022-01-01","kind":"exercise","acquired":true,"shares":2403,"ownership":{"direct":true},"footnotes":[{"field":"price","element":"transactionPricePerShare","label":"F1","text":"Each restricted stock unit (\"RSU\") represents a contingent right to receive one share of common stock."}],"balance_after":987992,"source":{"system":"sec-edgar","filing":"0000899243-22-006554","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924322006554/doc4.xml","form_type":"4"}},{"id":2556855,"issuer":{"id":94837,"kind":"organization","name":"EngageSmart, Inc.","symbol":"ESMT"},"owners":[{"id":47765,"kind":"person","name":"Bennett Robert Paul","position":1,"cik":"0001881869","reported_name":"Bennett Robert Paul","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Restricted Stock Unit","published_at":"2021-09-30T00:10:26.000Z","date":"2021-09-27","kind":"grant","acquired":true,"shares":38461,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F2","text":"Each restricted stock unit (\"RSU\") represents a contingent right to receive one share of common stock."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F3","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."},{"field":"derivative.expiration_date","element":"expirationDate","label":"F3","text":"The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date."}],"balance_after":38461,"derivative":{"underlying":"Common Stock","underlying_shares":38461},"source":{"system":"sec-edgar","filing":"0000899243-21-038233","document":"doc4.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1881869/000089924321038233/doc4.xml","form_type":"4"}}],"next_cursor":"2021-09-30T00:10:26.000000Z,2556855"}