Upland Software (NASDAQ: UPLD) insider logs new stock dealings

Rhea-AI Filing Summary

Upland Software, Inc. (symbol: UPLD) is the issuer of record for a Form 4 filing submitted to the SEC.

Insider Trade Summary

Net Buyer: 30,000 shares

Net Buy 2 txns

Insider Simon Jennifer L.

Role Chief Financial Officer

Type	Security	Shares	Price	Value
Grant/Award	Performance Share Unit F2	6,666	$0.00	$0.00
Grant/Award	Common Stock F1	30,000	$0.00	$0.00

Holdings After Transaction: Performance Share Unit — 6,666 shares (Direct); Common Stock — 30,000 shares (Direct)

Footnotes (2)

1. F1. The restricted stock units vest in twelve equal quarterly installments starting on the Vesting Commencement Date of September 30, 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. F2. Performance Stock Units ("PSUs") may vest at target amount of 6,666 and up to a maximum number of shares of 25,000 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 August 17, 2026 and ending on August 16, 2029, the Performance Period. PSUs may vest as follows a) 6,666 shares at $20.00, b) 1,222 shares at $22.00, c) 1,223 shares at $24.00, d) 1,222 shares at $26.00, e) 1,222 shares at $28.00, f) 1,222 shares at $30.00, g) 1,223 shares at $32.00, h) 1,222 shares at $34.00, i) 1,222 shares at $36.00, j) 1,222 shares at $38.00, k) 1,223 shares at $40.00, l) 1,222 shares at $42.00, m) 1,222 shares at $44.00, n) 1,222 shares at $46.00, o) 1,223 shares at $48.00, and p) 1,222 shares at $50.00.

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Form 4 Insider Transactions: What Each Field Means →

Available on EDGAR 08/18/2026 - 04:26 PM Accepted by SEC EDGAR 08/18/2026 - 04:25 PM Learn about SEC filing dates

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

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

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^*

Simon Jennifer L.

(Last) (First) (Middle)

900 S. CAPITAL OF TEXAS HWY

LAS CIMAS IV, SUITE 300

(Street)

AUSTIN TEXAS 78746

(City) (State) (Zip)

UNITED STATES

(Country)

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)
	Chief Financial Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
08/17/2026

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

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

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

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)
			Code	V	Amount	(A) or (D)	Price
Common Stock	08/17/2026		A		30,000(1)	A	$0	30,000	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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Performance Share Unit	$0	08/17/2026		A		6,666		(2)	08/16/2029	Common Stock	6,666	$0	6,666	D

Explanation of Responses:

1. The restricted stock units vest in twelve equal quarterly installments starting on the Vesting Commencement Date of September 30, 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 6,666 and up to a maximum number of shares of 25,000 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 August 17, 2026 and ending on August 16, 2029, the Performance Period. PSUs may vest as follows a) 6,666 shares at $20.00, b) 1,222 shares at $22.00, c) 1,223 shares at $24.00, d) 1,222 shares at $26.00, e) 1,222 shares at $28.00, f) 1,222 shares at $30.00, g) 1,223 shares at $32.00, h) 1,222 shares at $34.00, i) 1,222 shares at $36.00, j) 1,222 shares at $38.00, k) 1,223 shares at $40.00, l) 1,222 shares at $42.00, m) 1,222 shares at $44.00, n) 1,222 shares at $46.00, o) 1,223 shares at $48.00, and p) 1,222 shares at $50.00.

Remarks:

	Melanie Marshall (attorney-in-fact for J. Simon)	08/18/2026
	** 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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)