Upland Software, Inc. — Director's Dealing 2021

Jul 2, 2021

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: Upland Software, Inc. (UPLD)
CIK: 0001505155
Period of Report: 2021-06-30

Reporting Person: MCDONALD JOHN T (Director, CEO)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2021-06-30	Common Stock	M	135345	—	Acquired	1490447	Direct
2021-07-02	Common Stock	S	52740	$41.5772	Disposed	1437707	Direct

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2021-06-30	Performance Share Unit	$0.0	M	66297	Disposed		Common Stock (66297.0)	Direct

Holdings (Non-Derivative)

Security	Shares	Ownership
Common Stock	153738	Indirect

Footnotes

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.