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The percentage of PSUs that may vest will be a) 0% if TSR is below 5%, b) 50% if TSR is 5%, c) 62.5% if TSR is 6.25%, d) 75% if TSR is 7.50%, e) 87.5% if TSR is 8.75%, f) 100% if TSR is 10%, g) 125% if TSR is 11.25%, h) 150% if TSR is 12.50%, i) 175% if TSR is 13.75%, j) 200% if TSR is 15%, k) 225% if TSR is 16.75%, l) 250% if TSR is 18.50%, m) 275% if TSR is 19.25%, and n) 300% if TSR is 20% or greater. 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The percentage of PSUs that may vest will be a) 0% if TSR is below 5%, b) 50% if TSR is 5%, c) 62.5% if TSR is 6.25%, d) 75% if TSR is 7.50%, e) 87.5% if TSR is 8.75%, f) 100% if TSR is 10%, g) 125% if TSR is 11.25%, h) 150% if TSR is 12.50%, i) 175% if TSR is 13.75%, j) 200% if TSR is 15%, k) 225% if TSR is 16.75%, l) 250% if TSR is 18.50%, m) 275% if TSR is 19.25%, and n) 300% if TSR is 20% or greater. The percentage of PSUs that may vest is determined using linear interpolation."}],"balance_after":562500,"derivative":{"exercise_price":0,"expiration_date":"2027-02-28","underlying":"Common Stock","underlying_shares":31250},"source":{"system":"sec-edgar","filing":"0001505155-24-000112","document":"wk-form4_1733441797.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":9,"url":"https://www.sec.gov/Archives/edgar/data/1094792/000150515524000112/wk-form4_1733441797.xml","form_type":"4"}},{"id":1342004,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":50078,"kind":"person","name":"MCDONALD JOHN T","position":1,"cik":"0001094792","reported_name":"MCDONALD JOHN T","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO"}}],"security":"Performance Share Unit","published_at":"2024-12-05T23:36:44.000Z","date":"2024-12-03","kind":"exercise","planned":false,"acquired":false,"shares":156250,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_date","element":"exerciseDate","label":"F6","text":"The total maximum potential of 750,000 PSUs is the balance of the 250,000 PSUs, as disclosed on Form 4 filed on January 29, 2024, as amended on January 31, 2024, and 500,000 PSUs as disclosed on Form 4 filed on June 5, 2024.  0% to 300% of these PSUs may vest based on the achievement of the Company's TSR goals for any 30 consecutive trading days immediately preceding any such date during the period beginning on February 28, 2024, and ending on February 28, 2027- the Performance Period. The percentage of PSUs that may vest will be a) 0% if TSR is below 5%, b) 50% if TSR is 5%, c) 62.5% if TSR is 6.25%, d) 75% if TSR is 7.50%, e) 87.5% if TSR is 8.75%, f) 100% if TSR is 10%, g) 125% if TSR is 11.25%, h) 150% if TSR is 12.50%, i) 175% if TSR is 13.75%, j) 200% if TSR is 15%, k) 225% if TSR is 16.75%, l) 250% if TSR is 18.50%, m) 275% if TSR is 19.25%, and n) 300% if TSR is 20% or greater. The percentage of PSUs that may vest is determined using linear interpolation."}],"balance_after":593750,"derivative":{"exercise_price":0,"expiration_date":"2027-02-28","underlying":"Common Stock","underlying_shares":156250},"source":{"system":"sec-edgar","filing":"0001505155-24-000112","document":"wk-form4_1733441797.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":8,"url":"https://www.sec.gov/Archives/edgar/data/1094792/000150515524000112/wk-form4_1733441797.xml","form_type":"4"}},{"id":1342003,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":50078,"kind":"person","name":"MCDONALD JOHN T","position":1,"cik":"0001094792","reported_name":"MCDONALD JOHN T","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO"}}],"security":"Common Stock","published_at":"2024-12-05T23:36:44.000Z","date":"2024-12-05","kind":"tax_withholding","planned":false,"acquired":false,"shares":24594,"price":4.32,"value":106246.08,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F3","text":"Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of performance share units. This is not an open market sale of securities."},{"field":"balance_after","element":"sharesOwnedFollowingTransaction","label":"F2","text":"Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee."}],"balance_after":1978376,"source":{"system":"sec-edgar","filing":"0001505155-24-000112","document":"wk-form4_1733441797.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":7,"url":"https://www.sec.gov/Archives/edgar/data/1094792/000150515524000112/wk-form4_1733441797.xml","form_type":"4"}},{"id":1342002,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":50078,"kind":"person","name":"MCDONALD JOHN T","position":1,"cik":"0001094792","reported_name":"MCDONALD JOHN T","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO"}}],"security":"Common Stock","published_at":"2024-12-05T23:36:44.000Z","date":"2024-12-05","kind":"exercise","planned":false,"acquired":true,"shares":62500,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"shares","element":"transactionShares","label":"F5","text":"Based on the Company's total stockholder return (\"TSR\") an incremental approximate 25% (for a total of approximately 100%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and June 5, 2024, vested on December 5, 2024, in accordance with the terms of Mr. McDonald's performance grant."},{"field":"balance_after","element":"sharesOwnedFollowingTransaction","label":"F2","text":"Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee."}],"balance_after":2002970,"source":{"system":"sec-edgar","filing":"0001505155-24-000112","document":"wk-form4_1733441797.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":6,"url":"https://www.sec.gov/Archives/edgar/data/1094792/000150515524000112/wk-form4_1733441797.xml","form_type":"4"}},{"id":1342001,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":50078,"kind":"person","name":"MCDONALD JOHN T","position":1,"cik":"0001094792","reported_name":"MCDONALD JOHN T","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO"}}],"security":"Common Stock","published_at":"2024-12-05T23:36:44.000Z","date":"2024-12-04","kind":"tax_withholding","planned":false,"acquired":false,"shares":12297,"price":4,"value":49188.0,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F3","text":"Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of performance share units. This is not an open market sale of securities."},{"field":"balance_after","element":"sharesOwnedFollowingTransaction","label":"F2","text":"Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee."}],"balance_after":1940470,"source":{"system":"sec-edgar","filing":"0001505155-24-000112","document":"wk-form4_1733441797.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":5,"url":"https://www.sec.gov/Archives/edgar/data/1094792/000150515524000112/wk-form4_1733441797.xml","form_type":"4"}},{"id":1342000,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":50078,"kind":"person","name":"MCDONALD JOHN T","position":1,"cik":"0001094792","reported_name":"MCDONALD JOHN T","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO"}}],"security":"Common Stock","published_at":"2024-12-05T23:36:44.000Z","date":"2024-12-04","kind":"exercise","planned":false,"acquired":true,"shares":31250,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"shares","element":"transactionShares","label":"F4","text":"Based on the Company's total stockholder return (\"TSR\") an incremental approximate 12.5% (for a total of approximately 75%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and June 5, 2024, vested on December 4, 2024, in accordance with the terms of Mr. McDonald's performance grant."},{"field":"balance_after","element":"sharesOwnedFollowingTransaction","label":"F2","text":"Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee."}],"balance_after":1952767,"source":{"system":"sec-edgar","filing":"0001505155-24-000112","document":"wk-form4_1733441797.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":4,"url":"https://www.sec.gov/Archives/edgar/data/1094792/000150515524000112/wk-form4_1733441797.xml","form_type":"4"}},{"id":1341999,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":50078,"kind":"person","name":"MCDONALD JOHN T","position":1,"cik":"0001094792","reported_name":"MCDONALD JOHN T","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO"}}],"security":"Common Stock","published_at":"2024-12-05T23:36:44.000Z","date":"2024-12-03","kind":"tax_withholding","planned":false,"acquired":false,"shares":61484,"price":4.37,"value":268685.08,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F3","text":"Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of performance share units. This is not an open market sale of securities."},{"field":"balance_after","element":"sharesOwnedFollowingTransaction","label":"F2","text":"Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee."}],"balance_after":1921517,"source":{"system":"sec-edgar","filing":"0001505155-24-000112","document":"wk-form4_1733441797.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1094792/000150515524000112/wk-form4_1733441797.xml","form_type":"4"}},{"id":1341998,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":50078,"kind":"person","name":"MCDONALD JOHN T","position":1,"cik":"0001094792","reported_name":"MCDONALD JOHN T","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO"}}],"security":"Common Stock","published_at":"2024-12-05T23:36:44.000Z","date":"2024-12-03","kind":"exercise","planned":false,"acquired":true,"shares":156250,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"shares","element":"transactionShares","label":"F1","text":"Based on the Company's total stockholder return (\"TSR\") approximately 62.5% of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and June 5, 2024, vested on December 3, 2024, in accordance with the terms of Mr. McDonald's performance grant."},{"field":"balance_after","element":"sharesOwnedFollowingTransaction","label":"F2","text":"Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee."}],"balance_after":1983001,"source":{"system":"sec-edgar","filing":"0001505155-24-000112","document":"wk-form4_1733441797.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1094792/000150515524000112/wk-form4_1733441797.xml","form_type":"4"}},{"id":1363366,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":24512,"kind":"person","name":"Mattox Timothy","position":1,"cik":"0001624067","reported_name":"Mattox Timothy","relationship":{"director":true,"officer":false,"ten_percent_owner":false,"other":false}}],"security":"Common Stock","published_at":"2024-11-15T21:18:33.000Z","date":"2024-11-14","kind":"sale","planned":false,"acquired":false,"shares":18000,"price":2.5034,"value":45061.2,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Sales made to recognize general portfolio tax savings."},{"field":"price","element":"transactionPricePerShare","label":"F3","text":"This transaction was executed in multiple trades at prices ranging from $2.490 to $2.530. The price reported above reflects the weighted average sale price. The Reporting Person undertakes to provide upon request by the staff of the Securities and Exchange Commission, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate sale price."}],"balance_after":416776,"source":{"system":"sec-edgar","filing":"0001505155-24-000110","document":"wk-form4_1731705506.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1505155/000150515524000110/wk-form4_1731705506.xml","form_type":"4"}},{"id":1363365,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":24512,"kind":"person","name":"Mattox Timothy","position":1,"cik":"0001624067","reported_name":"Mattox Timothy","relationship":{"director":true,"officer":false,"ten_percent_owner":false,"other":false}}],"security":"Common Stock","published_at":"2024-11-15T21:18:33.000Z","date":"2024-11-13","kind":"sale","planned":false,"acquired":false,"shares":2000,"price":2.6358,"value":5271.6,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Sales made to recognize general portfolio tax savings."},{"field":"price","element":"transactionPricePerShare","label":"F2","text":"This transaction was executed in multiple trades at prices ranging from $2.630 to $2.730. The price reported above reflects the weighted average sale price. The Reporting Person undertakes to provide upon request by the staff of the Securities and Exchange Commission, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate sale price."}],"balance_after":434776,"source":{"system":"sec-edgar","filing":"0001505155-24-000110","document":"wk-form4_1731705506.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1505155/000150515524000110/wk-form4_1731705506.xml","form_type":"4"}},{"id":1376938,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":73805,"kind":"person","name":"Chung David H S","position":1,"cik":"0001576150","reported_name":"Chung David H S","relationship":{"director":true,"officer":false,"ten_percent_owner":false,"other":false}}],"security":"Common Stock","published_at":"2024-11-04T22:11:46.000Z","date":"2024-11-04","kind":"grant","planned":false,"acquired":true,"shares":25000,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"shares","element":"transactionShares","label":"F1","text":"Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/24 and the remaining shall vest in two equal quarterly installments on each of 3/16/25 and 6/16/25, provided Mr. Chung continues to serve as a Director of Upland Software, Inc. (the \"Issuer\") as of each date. Upon any subsequent disposition of common stock of the Issuer covered by the RSUs, Mr. Chung will transfer the proceeds from any such disposition to HGGC, LLC or its affiliates (\"HGGC\") as required by an agreement between Mr. Chung and HGGC. 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