Sec Form 4 Filing - MCDONALD JOHN T @ Upland Software, Inc. - 2024-12-03

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person MCDONALD JOHN T 2. Issuer Name and Ticker or Trading Symbol Upland Software, Inc. [ UPLD] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) CEO (Last) (First) (Middle) 401 CONGRESS AVENUE, SUITE 1850 3. Date of Earliest Transaction (MM/DD/YY) 12/03/2024 (Street) AUSTIN, TX78701 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock 363,738 I By National Financial Services as Cust FBO J. McDonald RRA Common Stock 12/03/2024 M 156,250 ( 1 ) A $ 0 1,983,001 ( 2 ) D Common Stock 12/03/2024 F( 3 ) 61,484 D $ 4.37 1,921,517 ( 2 ) D Common Stock 12/04/2024 M 31,250 ( 4 ) A $ 0 1,952,767 ( 2 ) D Common Stock 12/04/2024 F( 3 ) 12,297 D $ 4 1,940,470 ( 2 ) D Common Stock 12/05/2024 M 62,500 ( 5 ) A $ 0 2,002,970 ( 2 ) D Common Stock 12/05/2024 F( 3 ) 24,594 D $ 4.32 1,978,376 ( 2 ) D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Performance Share Unit $ 0 12/03/2024 M 156,250 ( 6 ) 02/28/2027 Common Stock 156,250 $ 0 593,750 D Performance Share Unit $ 0 12/04/2024 M 31,250 ( 6 ) 02/28/2027 Common Stock 31,250 $ 0 562,500 D Performance Share Unit $ 0 12/05/2024 M 62,500 ( 6 ) 02/28/2027 Common Stock 62,500 $ 0 500,000 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other MCDONALD JOHN T 401 CONGRESS AVENUE, SUITE 1850 AUSTIN, TX78701 X CEO Signatures /s/ Matthew Smith (as attorney-in-fact for J. McDonald) 12/05/2024 Signature of Reporting Person Date

Explanation of Responses:

( 1 )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. ( 2 )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. ( 3 )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. ( 4 )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. ( 5 )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. ( 6 )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.

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