UPLD Form 4: Michael Hill Reports 11,152-Share Withholding for RSU Taxes

Rhea-AI Filing Summary

Upland Software insider sale and tax withholding reported. Michael Douglass Hill, the company's CFO, Treasurer and Secretary, reported a disposition of 11,152 shares of Upland Software common stock on 09/16/2025 at a price of $2.48 per share. The filing states these shares were withheld by the issuer to satisfy tax withholding obligations related to the vesting of restricted stock units and explicitly notes this was not an open-market sale.

After the reported disposition, Mr. Hill directly beneficially owns 340,078 shares and indirectly owns 160,042 shares held in the MDH Trust for his family, for a total of 500,120 shares referenced in the filing.

Insights

Securities Compliance Analyst

TL;DR: Routine withholding to cover taxes on vested RSUs; procedural disclosure with no new open-market selling indicated.

The Form 4 documents a common administrative transaction: the issuer withheld 11,152 shares to satisfy tax withholding upon RSU vesting. The filing clarifies the transaction code and price ($2.48) and distinguishes the withholding from an open-market sale, reducing the risk of misinterpretation as active insider selling. Holdings after the transaction are clearly reported as 340,078 direct and 160,042 indirect (MDH Trust) shares, which preserves transparency around the reporting person’s economic stake.

Corporate Governance Expert

TL;DR: Disclosure aligns with Section 16 rules; transaction appears administrative and not materially adverse.

The report meets Section 16 disclosure requirements by itemizing the transaction date, amount, price, and nature of indirect ownership. Stating that the disposition was for tax withholding is important for governance transparency because it prevents misclassification of insider intent. The presence of an MDH Trust holding and the reporting person acting as trustee are appropriately disclosed, maintaining clarity on beneficial ownership structure.

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).

1. Name and Address of Reporting Person^*

Hill Michael Douglass

(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)
	CFO, Treasurer & Secretary

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)		11,152	D	$2.48	340,078	D
Common Stock								160,042	I	Held by MDH Trust(2)

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.

2. Share held by trust for the benefit of reporting person's family. Reporting person is the trustee of the trust.

Remarks:

	/s/ Micheal D. Hill	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 Michael D. Hill report on Form 4 for UPLD?

He reported a disposition of 11,152 shares on 09/16/2025 at $2.48 per share, withheld to satisfy tax obligations from RSU vesting.

Does the Form 4 indicate an open-market sale by the insider (UPLD)?

No. The filing explicitly states the shares were withheld by the issuer to satisfy tax withholding and were not an open-market sale.

How many UPLD shares does the reporting person own after the transaction?

After the transaction, the filing shows 340,078 shares owned directly and 160,042 shares indirectly via the MDH Trust, totaling 500,120 shares referenced.

What is the nature of the indirect ownership reported on the UPLD Form 4?

The indirect shares (160,042) are held by an MDH Trust for the benefit of the reporting person's family, and the reporting person is the trustee.

What transaction code and explanation were used on the Form 4?

Transaction code F(1) was used, with an explanation that shares were withheld to satisfy tax withholding obligations related to RSU vesting.