JOHN T. MCDONALD - 28 Jan 2025 Form 4 Insider Report for Upland Software, Inc. (UPLD)

Role: CEO, Director
Signature: /s/ Matthew Smith (as attorney-in-fact for J. McDonald)
Issuer symbol: UPLD
Transactions as of: 28 Jan 2025
Transactions value $: $0
Form type: 4
Filing time: 30 Jan 2025, 17:17:12 UTC
Previous filing: 17 Dec 2024
Next filing: 17 Mar 2025
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPLD	Common Stock	Award	$0	+250,000	+11%	$0.000000	2,513,793	28 Jan 2025	Direct	F1
holding	UPLD	Common Stock						363,738	28 Jan 2025	By National Financial Services as Cust FBO J. McDonald RRA	F2

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	UPLD	Performance Share Unit	Award	$0	+250,000		$0.000000	250,000	28 Jan 2025	Common Stock	250,000	$0.000000	Direct	F3

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	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.
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	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.