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This is not an open market sale of securities."}],"balance_after":48574,"source":{"system":"sec-edgar","filing":"0001870221-26-000013","document":"wk-form4_1790026719.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1870221/000187022126000013/wk-form4_1790026719.xml","form_type":"4"}},{"id":736399,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":37739,"kind":"person","name":"Nathaniel Sean","position":1,"cik":"0001870221","reported_name":"Nathaniel Sean","relationship":{"director":false,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO and President"}}],"security":"Common Stock","published_at":"2026-06-16T22:33:35.000Z","date":"2026-06-16","kind":"tax_withholding","planned":false,"acquired":false,"shares":18605,"price":0.6064,"value":11282.072,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities."}],"balance_after":502146,"source":{"system":"sec-edgar","filing":"0001870221-26-000009","document":"wk-form4_1781649213.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1870221/000187022126000009/wk-form4_1781649213.xml","form_type":"4"}},{"id":746430,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":37739,"kind":"person","name":"Nathaniel Sean","position":1,"cik":"0001870221","reported_name":"Nathaniel Sean","relationship":{"director":false,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO and President"}}],"security":"Performance-based Restricted Stock Unit June 2026","published_at":"2026-06-08T20:51:18.000Z","date":"2026-06-04","kind":"grant","planned":false,"acquired":true,"shares":133333,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_date","element":"exerciseDate","label":"F2","text":"Performance Stock Units (\"PSUs\") may vest at target amount of 133,333 and up to a maximum number of shares of 500,000 upon the achievement of the stock price hurdles for thirty (30) consecutive trading days immediately preceding such date during the three-year performance period beginning on May 1, 2026 and ending on May 1, 2029, the Performance Period. PSUs may vest as follows a) 133,333 shares at $2.00, b) 24,445 shares at $2.20, c) 24,444 shares at $2.40, d) 24,445 shares at $2.60, e) 24,444 shares at $2.80, f) 24,445 shares at $3.00, g) 24,444 shares at $3.20, h) 24,445 shares at $3.40, i) 24,444 shares at $3.60, j) 24,445 shares at $3.80, k) 24,444 shares at $4.00, l) 24,445 shares at $4.20, m) 24,444 shares at $4.40, n) 24,445 shares at $4.60, o) 24,444 shares at $4.80, and p) 24,444 shares at $5.00."}],"balance_after":133333,"derivative":{"exercise_price":0,"expiration_date":"2029-05-01","underlying":"Common Stock","underlying_shares":133333},"source":{"system":"sec-edgar","filing":"0001870221-26-000007","document":"wk-form4_1780951876.xml","document_sequence":1,"table":"derivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1870221/000187022126000007/wk-form4_1780951876.xml","form_type":"4"}},{"id":746429,"issuer":{"id":7891,"kind":"organization","name":"Upland Software, Inc.","symbol":"UPLD"},"owners":[{"id":37739,"kind":"person","name":"Nathaniel Sean","position":1,"cik":"0001870221","reported_name":"Nathaniel Sean","relationship":{"director":false,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"CEO and President"}}],"security":"Common Stock","published_at":"2026-06-08T20:51:18.000Z","date":"2026-06-04","kind":"grant","planned":false,"acquired":true,"shares":500000,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"shares","element":"transactionShares","label":"F1","text":"The restricted stock units vest in twelve equal quarterly installments starting on the Vesting Commencement Date of June 16, 2026, provided that the participant continues to be a service provider through each such vesting date.  Notwithstanding the foregoing, in the event of the participant's termination by the Company for any reason other than cause or if participant leaves for Good Reason after a Change in Control (as defined in the Plan), then 100% of the restricted stock units shall become fully vested."}],"balance_after":520751,"source":{"system":"sec-edgar","filing":"0001870221-26-000007","document":"wk-form4_1780951876.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1870221/000187022126000007/wk-form4_1780951876.xml","form_type":"4"}},{"id":2624041,"issuer":{"id":6054,"kind":"organization","name":"CS Disco, Inc."},"owners":[{"id":37739,"kind":"person","name":"Nathaniel Sean","position":1,"cik":"0001870221","reported_name":"Nathaniel Sean","relationship":{"director":false,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Operating Officer"}}],"security":"Common Stock","published_at":"2021-07-27T23:30:15.000Z","date":"2021-07-23","kind":"purchase","acquired":true,"shares":912,"price":32,"value":29184.0,"ownership":{"direct":true},"balance_after":912,"source":{"system":"sec-edgar","filing":"0001209191-21-048360","document":"doc4.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1870221/000120919121048360/doc4.xml","form_type":"4"}}]}