[Form 4] Upland Software, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Upland Software insider reported a withholding of 26,236 shares to cover taxes on vested restricted stock units. The transaction occurred on 09/16/2025 at a reported price of $2.48 per share and reduced the reporting person’s beneficial holdings to 731,852 shares. The reporting person is identified as Doman Dan, noted as an officer with the title Chief Operating & Product Ofcr and marked as a director. The filing clarifies this was shares withheld by the issuer to satisfy tax withholding obligations and explicitly states it is not an open market sale. The Form 4 was signed by an attorney-in-fact on 09/17/2025.

Positive

• Transaction is a tax-withholding on vested RSUs, explicitly stated as not an open market sale
• Filing discloses officer title and director status for clarity on the reporting person’s role

Negative

• Beneficial ownership decreased by 26,236 shares to 731,852 shares following the withholding
• Reported price of $2.48 provides a reference point but no cash proceeds or market activity are reported

Insights

Financial Analyst

TL;DR: Routine tax-withholding reduced insider holdings; no open-market sale or new cash proceeds reported.

The Form 4 documents a common post-vesting administrative action: 26,236 shares were withheld to satisfy tax obligations at $2.48 per share, lowering beneficial ownership to 731,852 shares. Because the filing states this is not an open market sale, there is no change in market-implied demand from this action. For investors, this is a non-economic disposition that does not indicate a change in insider sentiment based on the information provided.

Corporate Governance Expert

TL;DR: Disclosure is standard and compliant; signature by attorney-in-fact is noted.

The Form 4 appropriately discloses the nature of the transaction as issuer withholding for tax purposes and includes the reporting person’s officer title and director checkmark. The document includes the required signature block executed by an attorney-in-fact on 09/17/2025. No governance red flags or indicia of unusual insider activity are evident within the filing.

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^*

Doman Dan

(Last) (First) (Middle)

900 S. CAPITAL OF TEXAS HWY

LAS CIMAS IV, SUITE 300

(Street)

AUSTIN TX 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)
	Chief Operating & Product Ofcr

3. Date of Earliest Transaction (Month/Day/Year)
09/16/2025

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)
			Code	V	Amount	(A) or (D)	Price
Common Stock	09/16/2025		F(1)		26,236	D	$2.48	731,852	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

Explanation of Responses:

1. Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Remarks:

	/s/ Michael D. Hill (as attorney-in-fact for D. Doman)	09/17/2025
	** 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.

FAQ

What did UPLD insider Doman Dan report on the Form 4?

The Form 4 reports that 26,236 shares were withheld to satisfy tax withholding on vested restricted stock units; the filing states this was not an open market sale.

When did the transaction occur and at what price?

The transaction date is 09/16/2025 and the reported price is $2.48 per share.

How many shares does Doman Dan beneficially own after the transaction?

After the withholding, the filing shows 731,852 shares beneficially owned.

What is the reported reason for the share transfer?

The filing explains the shares were withheld by the issuer to satisfy tax withholding obligations related to RSU vesting.

Who signed the Form 4 and when?

The Form 4 is signed by Michael D. Hill as attorney-in-fact for D. Doman on 09/17/2025.