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Upland Software, Inc. Director's Dealing 2024

Dec 5, 2024

34321_dirs_2024-12-05_f7a84f26-365c-4978-ac4a-5ed9c0d19e18.zip

Director's Dealing

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SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: Upland Software, Inc. (UPLD)
CIK: 0001505155
Period of Report: 2024-12-03

Reporting Person: MCDONALD JOHN T (Director, CEO)

Non-Derivative Transactions

Date Security Code Shares Price A/D Holdings After Ownership
2024-12-03 Common Stock M 156250 Acquired 1983001 Direct
2024-12-03 Common Stock F 61484 $4.37 Disposed 1921517 Direct
2024-12-04 Common Stock M 31250 Acquired 1952767 Direct
2024-12-04 Common Stock F 12297 $4 Disposed 1940470 Direct
2024-12-05 Common Stock M 62500 Acquired 2002970 Direct
2024-12-05 Common Stock F 24594 $4.32 Disposed 1978376 Direct

Derivative Transactions

Date Security Exercise Price Code Shares A/D Expiration Underlying Ownership
2024-12-03 Performance Share Unit $0 M 156250 Disposed 2027-02-28 Common Stock (156250) Direct
2024-12-04 Performance Share Unit $0 M 31250 Disposed 2027-02-28 Common Stock (31250) Direct
2024-12-05 Performance Share Unit $0 M 62500 Disposed 2027-02-28 Common Stock (62500) Direct

Holdings (Non-Derivative)

Security Shares Ownership
Common Stock 363738 Indirect

Footnotes

F1: 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.

F2: 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.

F3: 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.

F4: 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.

F5: 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.

F6: 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.