SEC FORM 4

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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).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Nathaniel Sean

(Last)

(First)

(Middle)

900 S. CAPITAL OF TEXAS HWY

LAS CIMAS IV, SUITE 300

(Street)

AUSTIN

78746

(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)

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

3. Date of Earliest Transaction (Month/Day/Year)
06/04/2026

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	06/04/2026		A		500,000⁽¹⁾	A	$0	520,751	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-based Restricted Stock Unit June 2026	$0	06/04/2026		A		133,333		⁽²⁾	05/01/2029	Common Stock	133,333	$0	133,333	D

Explanation of Responses:

1. The restricted stock units vest in twelve equal quarterly installments starting on the Vesting Commencement Date of June 16, 2026, provided that the participant continues to be a service provider through each such vesting date. Notwithstanding the foregoing, in the event of the participant's termination by the Company for any reason other than cause or if participant leaves for Good Reason after a Change in Control (as defined in the Plan), then 100% of the restricted stock units shall become fully vested.

2. Performance Stock Units ("PSUs") may vest at target amount of 133,333 and up to a maximum number of shares of 500,000 upon the achievement of the stock price hurdles for thirty (30) consecutive trading days immediately preceding such date during the three-year performance period beginning on May 1, 2026 and ending on May 1, 2029, the Performance Period. PSUs may vest as follows a) 133,333 shares at $2.00, b) 24,445 shares at $2.20, c) 24,444 shares at $2.40, d) 24,445 shares at $2.60, e) 24,444 shares at $2.80, f) 24,445 shares at $3.00, g) 24,444 shares at $3.20, h) 24,445 shares at $3.40, i) 24,444 shares at $3.60, j) 24,445 shares at $3.80, k) 24,444 shares at $4.00, l) 24,445 shares at $4.20, m) 24,444 shares at $4.40, n) 24,445 shares at $4.60, o) 24,444 shares at $4.80, and p) 24,444 shares at $5.00.

Remarks:

	/s/ Michael D. Hill (as attorney-in-fact for S. Nathaniel)	06/08/2026
	** 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).
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