Mcdonald John T. - 03 Dec 2024 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: 03 Dec 2024
Net transactions value: -$424,119
Form type: 4
Filing time: 05 Dec 2024, 18:36:44 UTC
Previous filing: 17 Sep 2024
Next filing: 10 Dec 2024
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPLD	Common Stock	Options Exercise	$0	+156,250	+8.6%	$0.000000	1,983,001	03 Dec 2024	Direct	F1, F2
transaction	UPLD	Common Stock	Tax liability	$268,685	-61,484	-3.1%	$4.37	1,921,517	03 Dec 2024	Direct	F2, F3
transaction	UPLD	Common Stock	Options Exercise	$0	+31,250	+1.6%	$0.000000	1,952,767	04 Dec 2024	Direct	F2, F4
transaction	UPLD	Common Stock	Tax liability	$49,188	-12,297	-0.63%	$4.00	1,940,470	04 Dec 2024	Direct	F2, F3
transaction	UPLD	Common Stock	Options Exercise	$0	+62,500	+3.2%	$0.000000	2,002,970	05 Dec 2024	Direct	F2, F5
transaction	UPLD	Common Stock	Tax liability	$106,246	-24,594	-1.2%	$4.32	1,978,376	05 Dec 2024	Direct	F2, F3
holding	UPLD	Common Stock						363,738	03 Dec 2024	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	-156,250	-21%	$0.000000	593,750	03 Dec 2024	Common Stock	156,250	$0.000000	Direct	F6
transaction	UPLD	Performance Share Unit	Options Exercise	$0	-31,250	-5.3%	$0.000000	562,500	04 Dec 2024	Common Stock	31,250	$0.000000	Direct	F6
transaction	UPLD	Performance Share Unit	Options Exercise	$0	-62,500	-11%	$0.000000	500,000	05 Dec 2024	Common Stock	62,500	$0.000000	Direct	F6

* 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") approximately 62.5% of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and June 5, 2024, vested on December 3, 2024, 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 withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of performance share units. This is not an open market sale of securities.
F4	Based on the Company's total stockholder return ("TSR") an incremental approximate 12.5% (for a total of approximately 75%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and June 5, 2024, vested on December 4, 2024, in accordance with the terms of Mr. McDonald's performance grant.
F5	Based on the Company's total stockholder return ("TSR") an incremental approximate 25% (for a total of approximately 100%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and June 5, 2024, vested on December 5, 2024, in accordance with the terms of Mr. McDonald's performance grant.
F6	The total maximum potential of 750,000 PSUs is the balance of the 250,000 PSUs, as disclosed on Form 4 filed on January 29, 2024, as amended on January 31, 2024, and 500,000 PSUs as disclosed on Form 4 filed on June 5, 2024. 0% to 300% of these PSUs may vest based on the achievement of the Company's TSR goals for any 30 consecutive trading days immediately preceding any such date during the period beginning on February 28, 2024, and ending on February 28, 2027- 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.