Sec Form 4 Filing - MCDONALD JOHN T @ Upland Software, Inc. - 2025-01-28

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) 01/28/2025 (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 01/28/2025 A 250,000 ( 1 ) A $ 0 2,513,793 D Common Stock 363,738 I By National Financial Services as Cust FBO J. McDonald RRA ( 2 )

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 01/28/2025 A 250,000 ( 3 ) 02/28/2028 Common Stock 250,000 $ 0 250,000 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) 01/29/2025 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The restricted stock units vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2024, provided that the participant continues to be a service provider through each such vesting date, except as otherwise specified in the Executive Employment Agreement between the Company and participant. ( 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 )0% to 300% of these Performance Stock Units ("PSUs") may vest based on the achievement of the Company's total stockholder return ("TSR") goals for any 30 consecutive trading days immediately preceding any such date during the period beginning on February 28, 2025, and ending on February 28, 2028, 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.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

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