Upland Software (NASDAQ: UPLD) CFO uses shares to cover tax bill

Rhea-AI Filing Summary

Upland Software, Inc. CFO, Treasurer & Secretary Michael Douglass Hill reported a routine tax-related share disposition. On March 16, 2026, 8,931 shares of common stock were withheld by the company at $0.54 per share to cover tax obligations from vesting restricted stock units. This was explicitly described as not an open-market sale. After this withholding, Hill directly owned 392,291 common shares and indirectly held 160,042 shares through the MDH Trust, where he serves as trustee for his family.

Insider Trade Summary

2 transactions reported

Mixed 2 txns

Insider Hill Michael Douglass

Role CFO, Treasurer & Secretary

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock	8,931	$0.54	$5K
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 392,291 shares (Direct); Common Stock — 160,042 shares (Indirect, Held by MDH Trust)

Footnotes (1)

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

Form 4 Insider Transactions: What Each Field Means →

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^*

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)
03/16/2026

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)
			Code	V	Amount	(A) or (D)	Price
Common Stock	03/16/2026		F(1)		8,931	D	$0.54	392,291	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. Shares held by trust for the benefit of reporting person's family. Reporting person is the trustee of the trust.

Remarks:

	/s/ Micheal D. Hill	03/17/2026
	** 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.

FAQ

What insider transaction did Upland Software (UPLD) report for its CFO?

Upland Software CFO Michael Douglass Hill had 8,931 shares withheld to cover taxes on vesting restricted stock units. This was a non-market, administrative transaction where the issuer retained shares instead of the executive selling them in the open market.

Was the Upland Software (UPLD) CFO’s Form 4 transaction an open-market sale?

No, the filing states it was not an open-market sale. The 8,931 shares of common stock were withheld by the company solely to satisfy tax withholding obligations tied to restricted stock unit vesting, rather than being sold on a stock exchange.

How many Upland Software (UPLD) shares does the CFO hold after this Form 4?

After the tax withholding, Michael Douglass Hill directly owned 392,291 shares of Upland Software common stock. He also indirectly held 160,042 shares through the MDH Trust, which is identified as a trust for the benefit of his family.

What does the MDH Trust holding mean in the Upland Software (UPLD) Form 4?

The MDH Trust holds 160,042 Upland Software shares for the benefit of the CFO’s family. The filing explains that the reporting person is the trustee of this trust, so these shares are reported as indirectly owned common stock in the Form 4.

How is the tax withholding transaction described in Upland Software (UPLD) CFO’s Form 4?

The Form 4 describes it as “payment of tax liability by delivering securities.” Specifically, shares were withheld by the issuer to satisfy tax withholding obligations related to restricted stock unit vesting, which the footnote clarifies is not an open-market securities sale.