John T. Mcdonald - Dec 6, 2024 Form 4 Insider Report for Upland Software, Inc. (UPLD)

Role
CEO, Director
Signature
/s/ Matthew Smith (as attorney-in-fact for J. McDonald)
Stock symbol
UPLD
Transactions as of
Dec 6, 2024
Transactions value $
-$960,632
Form type
4
Date filed
12/10/2024, 05:49 PM
Previous filing
Dec 5, 2024
Next filing
Dec 17, 2024

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction UPLD Common Stock Options Exercise $0 +188K +9.48% $0.00 2.17M Dec 6, 2024 Direct F1, F2
transaction UPLD Common Stock Tax liability -$328K -73.8K -3.41% $4.45 2.09M Dec 6, 2024 Direct F2, F3
transaction UPLD Common Stock Options Exercise $0 +125K +5.97% $0.00 2.22M Dec 9, 2024 Direct F2, F4
transaction UPLD Common Stock Tax liability -$241K -49.2K -2.22% $4.89 2.17M Dec 9, 2024 Direct F2, F3
transaction UPLD Common Stock Options Exercise $0 +188K +8.65% $0.00 2.36M Dec 10, 2024 Direct F2, F5
transaction UPLD Common Stock Tax liability -$392K -73.8K -3.13% $5.31 2.28M Dec 10, 2024 Direct F2, F3
holding UPLD Common Stock 364K Dec 6, 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 -188K -37.5% $0.00 313K Dec 6, 2024 Common Stock 188K $0.00 Direct F6
transaction UPLD Performance Share Unit Options Exercise $0 -125K -40% $0.00 188K Dec 9, 2024 Common Stock 125K $0.00 Direct F6
transaction UPLD Performance Share Unit Options Exercise $0 -188K -100% $0.00 0 Dec 10, 2024 Common Stock 188K $0.00 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") an incremental approximate 75% (for a total of approximately 175%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and the corresponding 500,000 PSUs from June 5, 2024, vested on December 6, 2024, in accordance with the terms of Mr. McDonald's performance grant as described below in FN 6.
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 50% (for a total of approximately 225%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and the corresponding 500,000 PSUs from June 5, 2024, vested on December 9, 2024, in accordance with the terms of Mr. McDonald's performance grant as described below in FN 6.
F5 Based on the Company's total stockholder return ("TSR") an incremental approximate 75% (for a total of approximately 300%) of the 250,000 PSUs awarded on January 29, 2024, as amended on January 31, 2024, and the corresponding 500,000 PSUs from June 5, 2024, vested on December 6, 2024, in accordance with the terms of Mr. McDonald's performance grant as described below in FN 6.
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.