Sec Form 4 Filing - MCDONALD JOHN T @ Upland Software, Inc. - 2024-06-05

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 AVE., STE 1850 3. Date of Earliest Transaction (MM/DD/YY) 06/05/2024 (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

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 06/05/2024( 1 ) 06/05/2024( 1 ) A 500,000 ( 2 ) 02/28/2027 Common Stock 500,000 $ 0 750,000 ( 3 ) D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other MCDONALD JOHN T 401 CONGRESS AVE., STE 1850 AUSTIN, TX78701 X CEO Signatures /s/ Matthew Smith (as attorney-in-fact for J. McDonald) 06/06/2024 Signature of Reporting Person Date

Explanation of Responses:

( 1 )This Performance Share Units (the "PSUs") grant, as disclosed in Upland Software, Inc.'s (the "Company's") 2024 proxy statement, was approved by the Compensation Committee of the Board of Directors of the Company on January 29, 2024, contingent upon shareholder approval of Upland Software, Inc.'s 2024 Omnibus Incentive Plan. On June 5, 2024, at the 2024 annual meeting of shareholders, the Company's shareholders approved the 2024 Omnibus Incentive Plan. ( 2 )0% to 100% 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 percentage of PSUs that may vest will be (a) 0% if TSR is at or below 10%, (b) 12.5% if TSR is 11.25%, (c) 25% if TSR is 12.5%, (d) 37.5% if TSR is 13.75%, (e) 50% if TSR is 15%, (f) 62.5% if TSR is 16.75%, (g) 75% if TSR is 18.5%, (h) 87.5% if TSR is 19.25%, and (i) 100% if TSR is 20% or greater. The percentage of PSUs that may vest is determined using linear interpolation. ( 3 )On June 5, 2024, at the 2024 annual meeting of shareholders, the Company's shareholders approved the 2024 Omnibus Incentive Plan, and, as a result, the PSUs earned pursuant to the vesting schedule set forth on the Form 4/A, as filed with the U.S. Securities and Exchange Commission on March 11, 2024, are limited to 250,000 PSUs.

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