Upland Software (UPLD) CFO awarded 70,000-share equity grant and reports trust holdings

Rhea-AI Filing Summary

Hill Michael Douglass reported acquisition or exercise transactions in this Form 4 filing.

Upland Software’s CFO, Treasurer & Secretary Michael Douglass Hill received an equity grant of 70,000 shares of common stock on February 23, 2026. The award was made at a stated price of $0.00 per share as a grant, not an open‑market purchase.

According to a footnote, these restricted stock units vest in twelve equal quarterly installments starting on the three‑month anniversary of the Vesting Commencement Date of December 16, 2025, subject to continued service or as otherwise specified in his executive employment agreement. Following the grant, Hill directly owns 401,222 common shares. He also has indirect ownership of 160,042 common shares held by the MDH Trust, a trust for the benefit of his family for which he serves as trustee.

Insider Trade Summary

Net Buyer: 70,000 shares

Net Buy 2 txns

Insider Hill Michael Douglass

Role CFO, Treasurer & Secretary

Type	Security	Shares	Price	Value
Grant/Award	Common Stock	70,000	$0.00	$0.00
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 401,222 shares (Direct); Common Stock — 160,042 shares (Indirect, Held by MDH Trust)

Footnotes (2)

1. F1. The restricted stock units vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2025, provided that the participant continues to be a service provider through each such vesting date, except as otherwise specified in the Executive Employment Agreement between the Company and participant.
2. F2. Shares held by trust for the benefit of reporting person's family. Reporting person is the trustee of the trust.

FAQ

What did Upland Software (UPLD) CFO Michael Douglass Hill report in this Form 4?

Upland Software CFO Michael Douglass Hill reported receiving a grant of 70,000 common shares on February 23, 2026. The grant was priced at $0.00 per share and reflects equity compensation rather than an open‑market stock purchase or sale.

How do the 70,000 UPLD shares granted to the CFO vest over time?

The 70,000 restricted stock units vest in twelve equal quarterly installments. Vesting begins on the three‑month anniversary of the Vesting Commencement Date of December 16, 2025, contingent on Hill continuing as a service provider or as modified by his executive employment agreement.

What is Michael Douglass Hill’s direct ownership in Upland Software (UPLD) after this filing?

After the reported grant, Michael Douglass Hill directly owns 401,222 shares of Upland Software common stock. This figure reflects his direct holdings following the 70,000‑share equity award reported as a grant or award acquisition transaction on February 23, 2026.

What indirect Upland Software (UPLD) holdings are associated with the MDH Trust?

The filing shows 160,042 Upland Software common shares held indirectly through the MDH Trust. The trust is for the benefit of Hill’s family, and he serves as trustee, meaning these shares are reported as indirectly owned in addition to his direct holdings.

Was the Upland Software (UPLD) CFO’s Form 4 transaction a market buy or sell?

The transaction was not a market buy or sell; it was a grant or award acquisition of 70,000 common shares at a stated price of $0.00 per share. It reflects stock‑based compensation rather than a discretionary trade in the open market.

What agreement governs vesting of the Upland Software (UPLD) CFO’s RSUs?

Vesting of Hill’s restricted stock units is tied to continued service and the Executive Employment Agreement between Upland Software and the participant. The units vest quarterly starting after the December 16, 2025 Vesting Commencement Date, unless the agreement provides otherwise.

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Form 4 Insider Transactions: What Each Field Means →

Accepted by SEC EDGAR 02/25/2026 - 05:53 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 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)
02/23/2026

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	02/23/2026		A		70,000(1)	A	$0	401,222	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. The restricted stock units vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2025, provided that the participant continues to be a service provider through each such vesting date, except as otherwise specified in the Executive Employment Agreement between the Company and participant.

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	02/25/2026
	** 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.