Upland Software CEO reports tax-withheld shares

Upland Software CEO John T. McDonald reported a routine tax-related share disposition.

Rhea-AI Filing Summary

Upland Software CEO John T. McDonald reported a routine tax-related share disposition. On the vesting of restricted stock units, 18,605 shares of Common Stock were withheld by the company at $0.54 per share to cover tax obligations, which the filing specifies is not an open market sale. After this withholding, McDonald directly owns 2,390,887 shares of Upland Software common stock. He also has an additional 363,738 shares held indirectly through an account at National Financial Services, and a footnote notes a separate 125,000 shares held in a trust for his children.

Insider Trade Summary

Exercise Price or Tax Liability: 18,605 shares

Exercise Price or Tax Liability 2 txns

Insider MCDONALD JOHN T

Role CEO

Type	Security	Shares	Price	Value
Exercise Price or Tax Liability	Common Stock	18,605	$0.54	$10K
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 2,390,887 shares (Direct); Common Stock — 363,738 shares (Indirect, By National Financial Services as Cust FBO J. McDonald RRA)

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. 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.

FAQ

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

What insider transaction did Upland Software (UPLD) report for CEO John T. McDonald?

Upland Software reported that CEO John T. McDonald had 18,605 shares of Common Stock withheld to cover tax obligations from vested restricted stock units. The filing emphasizes this was not an open market sale but a tax-withholding disposition by the issuer.

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

No, the Form 4 states the 18,605 shares were withheld by Upland Software to satisfy tax obligations from RSU vesting. A footnote explicitly clarifies this was not an open market sale of securities but an administrative tax-withholding transaction.

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

After the tax-withholding transaction, CEO John T. McDonald directly owns 2,390,887 shares of Upland Software Common Stock. The filing also shows 363,738 shares held indirectly through National Financial Services as custodian for his account, reflecting additional indirect ownership.

What price per share was used for the Upland Software (UPLD) tax-withholding shares?

The filing reports that the 18,605 withheld shares were valued at $0.54 per share. This price is used solely for the tax-withholding disposition related to restricted stock unit vesting, not as a reported open market transaction price.

Does the Upland Software (UPLD) Form 4 mention any shares held in trust for the CEO’s children?

Yes, a footnote states there are 125,000 shares of Upland Software common stock held in a trust for John T. McDonald’s children, with The Bryn Mawr Trust Company of Delaware serving as trustee over those shares.

What indirect Upland Software (UPLD) holdings are reported for the CEO on this Form 4?

The Form 4 lists 363,738 shares of Common Stock held indirectly “By National Financial Services as Cust FBO J. McDonald RRA.” This entry reflects indirect ownership separate from McDonald’s 2,390,887 directly held Upland Software shares.

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

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Accepted by SEC EDGAR 03/17/2026 - 04:33 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^*

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)
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)		18,605	D	$0.54	2,390,887(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)	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.