Upland Software, Inc. — Director's Dealing 2024

Dec 10, 2024

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: Upland Software, Inc. (UPLD)
CIK: 0001505155
Period of Report: 2024-12-06

Reporting Person: MCDONALD JOHN T (Director, CEO)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2024-12-06	Common Stock	M	187500	—	Acquired	2165876	Direct
2024-12-06	Common Stock	F	73781	$4.45	Disposed	2092095	Direct
2024-12-09	Common Stock	M	125000	—	Acquired	2217095	Direct
2024-12-09	Common Stock	F	49188	$4.89	Disposed	2167907	Direct
2024-12-10	Common Stock	M	187500	—	Acquired	2355407	Direct
2024-12-10	Common Stock	F	73781	$5.31	Disposed	2281626	Direct

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2024-12-06	Performance Share Unit	$0	M	187500	Disposed	2027-02-28	Common Stock (187500)	Direct
2024-12-09	Performance Share Unit	$0	M	125000	Disposed	2027-02-28	Common Stock (125000)	Direct
2024-12-10	Performance Share Unit	$0	M	187500	Disposed	2027-02-28	Common Stock (187500)	Direct

Holdings (Non-Derivative)

Security	Shares	Ownership
Common Stock	363738	Indirect

Footnotes

F1: Based on the Company's total stockholder return ("TSR") an incremental approximate 75% (for a total of approximately 175%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and the corresponding 500,000 PSUs from June 5, 2024, vested on December 6, 2024, in accordance with the terms of Mr. McDonald's performance grant as described below in FN 6.

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 50% (for a total of approximately 225%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and the corresponding 500,000 PSUs from June 5, 2024, vested on December 9, 2024, in accordance with the terms of Mr. McDonald's performance grant as described below in FN 6.

F5: Based on the Company's total stockholder return ("TSR") an incremental approximate 75% (for a total of approximately 300%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and the corresponding 500,000 PSUs from June 5, 2024, vested on December 6, 2024, in accordance with the terms of Mr. McDonald's performance grant as described below in FN 6.

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.