John T. Mcdonald - Jun 30, 2021 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: Jun 30, 2021
Transactions value $: -$2,192,782
Form type: 4
Date filed: 7/2/2021, 06:01 PM
Previous filing: Jun 21, 2021
Next filing: Sep 20, 2021

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPLD	Common Stock	Options Exercise	$0	+135K	+9.99%	$0.00	1.49M	Jun 30, 2021	Direct	F1, F2
transaction	UPLD	Common Stock	Sale	-$2.19M	-52.7K	-3.54%	$41.58	1.44M	Jul 2, 2021	Direct	F2, F3, F4
holding	UPLD	Common Stock						154K	Jun 30, 2021	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	Options Exercise	$0	-66.3K	-100%	$0.00^*	0	Jun 30, 2021	Common Stock	66.3K	$0.00	Direct	F5

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

Explanation of Responses:

Id	Content
F1	Based on the Company's total stockholder return ("TSR") for the 18 month period ending June 30, 2021, approximately 204% of the PSUs awarded on February 24, 2020 vested on June 30, 2021 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 were sold pursuant to a 10b5-1 plan to cover the tax withholding obligations in connection with the vesting of restricted stock units.
F4	The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $41.55 to $42.04, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote to this Form 4.
F5	0% to 300% of these TSR performance PSUs may vest on June 30, 2021 based on the Company's total stockholder return ("TSR") for the 18 month period ending June 30, 2021. 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.