Upland Software (UPLD) CEO McDonald reports RSU tax share withholding

Rhea-AI Filing Summary

Upland Software, Inc. CEO and director J. McDonald reported an automatic share withholding related to equity compensation. On 12/16/2025, 19,677 shares of Upland common stock were withheld by the company at a price of $1.485 per share to cover tax obligations tied to the vesting of restricted stock units, and the filing clarifies this was not an open market sale. After this transaction, McDonald beneficially owned 2,409,492 shares directly and 363,738 shares indirectly through National Financial Services as custodian for a retirement account. The disclosure also notes that these totals do not include 125,000 additional shares held in a trust for the benefit of McDonald’s children.

Insider Trade Summary

2 transactions reported

Mixed 2 txns

Insider MCDONALD JOHN T

Role CEO

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock	19,677	$1.485	$29K
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 2,409,492 shares (Direct); Common Stock — 363,738 shares (Indirect, By National Financial Services as Cust FBO J. McDonald RRA)

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. Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.

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^*

MCDONALD JOHN T

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	CEO

3. Date of Earliest Transaction (Month/Day/Year)
12/16/2025

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	12/16/2025		F(1)		19,677	D	$1.485	2,409,492(2)	D
Common Stock								363,738	I	By National Financial Services as Cust FBO J. McDonald RRA

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. Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.

Remarks:

	/s/ Michael D. Hill (as attorney-in-fact for J. McDonald)	12/17/2025
	** 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 insider transaction did Upland Software (UPLD) report for J. McDonald?

The filing shows that on 12/16/2025, 19,677 shares of Upland common stock were withheld by the issuer to satisfy tax withholding obligations from the vesting of restricted stock units, and it states this was not an open market sale.

At what price were Upland Software (UPLD) shares withheld for taxes?

The 19,677 shares withheld to cover tax obligations related to restricted stock unit vesting were valued at a price of $1.485 per share.

How many Upland Software (UPLD) shares does J. McDonald beneficially own after this transaction?

Following the reported withholding, J. McDonald beneficially owns 2,409,492 shares of Upland common stock directly and 363,738 shares indirectly through National Financial Services as custodian for a retirement account.

Does the Upland Software (UPLD) Form 4 involve an open market sale by J. McDonald?

No. The explanation states that the shares were withheld by the issuer to satisfy tax withholding obligations in connection with restricted stock unit vesting and that this is not an open market sale of securities.

Are there additional Upland Software (UPLD) shares associated with J. McDonald not counted in the reported totals?

Yes. The filing notes that the reported beneficial ownership does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald’s children, for which The Bryn Mawr Trust Company of Delaware serves as trustee.

What is J. McDonald’s role at Upland Software (UPLD)?

The reporting person, J. McDonald, is identified as both a director and an officer of Upland Software, Inc., with the title of CEO.