JOHN T. MCDONALD - 21 Feb 2023 Form 4 Insider Report for Upland Software, Inc. (UPLD)

Role: CEO, Director
Signature: /s/ Kin Gill, as attorney-in-fact for Mr. McDonald
Issuer symbol: UPLD
Transactions as of: 21 Feb 2023
Net transactions value: $0
Form type: 4
Filing time: 22 Feb 2023, 15:35:40 UTC
Previous filing: 20 Dec 2022
Next filing: 14 Mar 2023
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	+100,000	+6.3%	$0.000000	1,679,402	21 Feb 2023	Direct	F1, F2
holding	UPLD	Common Stock						243,738	21 Feb 2023	By National Financial Services as Cust FBO J. McDonald RRA

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	+100,000		$0.000000	100,000	21 Feb 2023	Common Stock	100,000	$0.000000	Direct	F4
holding	UPLD	Performance Share Unit						93,750	21 Feb 2023	Common Stock	93,750	$0.000000	Direct	F3

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

Explanation of Responses:

Id	Content
F1	Represents restricted stock units vesting in twelve equal quarterly installments starting on March 16, 2023 and ending on December 16, 2025; provided that the participant continues to be a service provider through each such vesting date.
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	Units will vest on the first date on which the closing price of Upland's common stock for any 30 consecutive trading days immediately preceding such date before June 30, 2023 equals or exceeds certain stock price hurdles. On June 30, 2023, a number of Units (if any) will vest based on the closing price of Upland's common stock on June 30, 2023 using linear interpolation. Total shares earned will be between 0% and 300% of the target number of shares reported.
F4	Units will vest on the first date on which the closing price of Upland's common stock for any 30 consecutive trading days immediately preceding such date before December 31, 2025 equals or exceeds certain stock price hurdles. On December 31, 2025, a number of Units (if any) will vest based on the closing price of Upland's common stock on December 31, 2025 using linear interpolation. Total shares earned will be between 0% and 200% of the target number of shares reported.