John T. Mcdonald - Jan 12, 2022 Form 4 Insider Report for Upland Software, Inc. (UPLD)

Role: CEO, Director
Signature: /s/ Kin Gill (as attorney-in-fact for Mr. McDonald)
Stock symbol: UPLD
Transactions as of: Jan 12, 2022
Transactions value $: $0
Form type: 4
Date filed: 1/14/2022, 05:05 PM
Previous filing: Dec 21, 2021
Next filing: Mar 15, 2022

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPLD	Common Stock	Award	$0	+93.8K	+6.61%	$0.00	1.51M	Jan 12, 2022	Direct	F1, F2
holding	UPLD	Common Stock						154K	Jan 12, 2022	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	+93.8K		$0.00	93.8K	Jan 12, 2022	Common Stock	93.8K	$0.00	Direct	F4
holding	UPLD	Performance Share Unit						61.4K	Jan 12, 2022	Common Stock	61.4K	$0.00	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, 2022 and ending on December 16, 2024; 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	0% to 300% of these TSR performance PSUs may vest on June 30, 2022 based on the Company's total stockholder return ("TSR") for the 18 month period ending June 30, 2022. The percentage of TSR Performance PSUs that may vest will be (a) 0% if TSR is below 5.0%; (b) 50% if TSR is 5.0%; (c) 100% if TSR is 10%; and (d) 300% if TSR is 20% or greater. If TSR is between 5.0% and 10% or between 10% and 20%, the percentage of TSR Performance RSUs that may vest is determined using linear interpolation.
F4	Units will vest on the first date on which the closing price of Upland's common stock for any thirty (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.