Upland Software CFO shares withheld for RSU taxes

Upland Software, Inc. reported a Form 4 for CFO, Treasurer & Secretary Michael Douglass Hill.

Rhea-AI Filing Summary

Upland Software, Inc. reported a Form 4 for CFO, Treasurer & Secretary Michael Douglass Hill. On June 16, 2026, 8,931 shares of common stock were disposed of at $0.6064 per share to satisfy tax withholding obligations tied to vesting restricted stock units, which is not an open-market sale. After this tax-withholding disposition, Hill directly holds 383,360 common shares and indirectly holds 160,042 common shares through the MDH Trust, where he serves as trustee for his family.

Insider Trade Summary

Exercise Price or Tax Liability: 8,931 shares

Exercise Price or Tax Liability 2 txns

Insider Hill Michael Douglass

Role CFO, Treasurer & Secretary

Type	Security	Shares	Price	Value
Exercise Price or Tax Liability	Common Stock	8,931	$0.6064	$5K
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 383,360 shares (Direct); Common Stock — 160,042 shares (Indirect, Held by MDH Trust)

Footnotes (2)

1. F1. 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. F2. Shares held by trust for the benefit of reporting person's family. Reporting person is the trustee of the trust.

Key Figures

Tax withholding shares: 8,931 shares Withholding price: $0.6064 per share Direct holdings after transaction: 383,360 shares +3 more

6 metrics

Tax withholding shares 8,931 shares Shares withheld to satisfy tax obligations on RSU vesting

Withholding price $0.6064 per share Value per share for tax-withholding disposition

Direct holdings after transaction 383,360 shares Common stock directly owned by CFO after June 16, 2026

Indirect holdings via MDH Trust 160,042 shares Common stock held by MDH Trust for CFO’s family

Tax-withholding dispositions 1 transaction, 8,931 shares Summary of F-code tax-withholding activity

Transaction date June 16, 2026 Date of tax-withholding and holdings entry

Key Terms

restricted stock units, tax withholding obligations, indirect ownership, trustee

4 terms

restricted stock units financial

"in connection with the vesting of restricted stock units."

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

tax withholding obligations financial

"Shares withheld by the issuer to satisfy tax withholding obligations in connection"

indirect ownership financial

"Held by MDH Trust"

trustee financial

"Reporting person is the trustee of the trust."

A trustee is a person or institution legally appointed to hold and manage assets or enforce an agreement on behalf of other people (beneficiaries). Think of a trustee as a neutral referee or custodian who must act in the beneficiaries’ best interests, follow the trust or contract rules, and handle distributions, recordkeeping and enforcement. Investors care because a trustworthy trustee protects their rights, ensures promised payments or remedies are delivered, and can influence recoveries if things go wrong.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

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

Upland Software reported that CFO Michael Douglass Hill had 8,931 common shares withheld to cover tax obligations from vesting restricted stock units. This Form 4 event is a tax-withholding disposition, not an open-market sale of UPLD shares by the executive.

How many Upland Software shares were involved in the CFO’s tax withholding?

The filing shows 8,931 Upland Software common shares were withheld at $0.6064 per share. These shares were used to satisfy tax withholding obligations on vesting restricted stock units, according to the footnote, and did not represent a market sale transaction.

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

After the reported tax-withholding disposition, CFO Michael Douglass Hill directly holds 383,360 Upland Software common shares. He also indirectly holds 160,042 common shares through the MDH Trust, which is a trust established for the benefit of his family.

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

No, the Form 4 specifies that the 8,931 shares were withheld by Upland Software to satisfy tax withholding obligations on vesting restricted stock units. The footnote clarifies this is not an open-market sale of UPLD securities by the executive.

What is the MDH Trust mentioned in the Upland Software Form 4 filing?

The MDH Trust holds 160,042 Upland Software common shares for the benefit of Michael Douglass Hill’s family. The Form 4 notes he is the trustee of this trust, so those shares are reported as indirectly owned by him through the MDH Trust.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 06/16/2026 - 06:34 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^*

Hill Michael Douglass

(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)
	CFO, Treasurer & Secretary

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/16/2026

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	06/16/2026		F(1)		8,931	D	$0.6064	383,360	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	06/16/2026
	** 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)