Mcdonald John T Form 4 Upland Software / JOHN T MCDONALD ownership change

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

1. Name and Address of Reporting Person^*

MCDONALD JOHN T

(Last)

(First)

(Middle)

401 CONGRESS AVENUE, SUITE 1850

(Street)

AUSTIN

78701

(City)

(State)

(Zip)

2. Issuer Name and Ticker or Trading Symbol
Upland Software, Inc. [ UPLD ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director	10% Owner
X	Officer (give title below)	Other (specify below)
CEO

3. Date of Earliest Transaction (Month/Day/Year)
12/06/2024

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock								363,738	I	By National Financial Services as Cust FBO J. McDonald RRA
Common Stock	12/06/2024		M		187,500⁽¹⁾	A	$0	2,165,876⁽²⁾	D
Common Stock	12/06/2024		F		73,781⁽³⁾	D	$4.45	2,092,095⁽²⁾	D
Common Stock	12/09/2024		M		125,000⁽⁴⁾	A	$0	2,217,095⁽²⁾	D
Common Stock	12/09/2024		F		49,188⁽³⁾	D	$4.89	2,167,907⁽²⁾	D
Common Stock	12/10/2024		M		187,500⁽⁵⁾	A	$0	2,355,407⁽²⁾	D
Common Stock	12/10/2024		F		73,781⁽³⁾	D	$5.31	2,281,626⁽²⁾	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Performance Share Unit	$0	12/06/2024		M			187,500	⁽⁶⁾	02/28/2027	Common Stock	187,500	$0	312,500	D
Performance Share Unit	$0	12/09/2024		M			125,000	⁽⁶⁾	02/28/2027	Common Stock	125,000	$0	187,500	D
Performance Share Unit	$0	12/10/2024		M			187,500	⁽⁶⁾	02/28/2027	Common Stock	187,500	$0	0	D

Explanation of Responses:

1. 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

Remarks:

	/s/ Matthew Smith (as attorney-in-fact for J. McDonald)	12/10/2024
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
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Mcdonald John T Form 4Upland Software / JOHN T MCDONALD ownership change