[Form 4] Upland Software, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Upland Software insider J. McDonald reported a tax-withholding disposition of restricted stock units on 09/16/2025. The filing shows 22,956 shares were withheld at an effective price of $2.48; the filer held 2,429,169 shares directly after the transaction and 363,738 shares indirectly through National Financial Services as custodian for J. McDonald. The report clarifies the withheld shares were to satisfy tax obligations and were not an open-market sale. The filing notes an additional 125,000 shares held in a trust for Mr. McDonald’s children are excluded from the reported beneficial ownership. The form is signed by an attorney-in-fact on 09/17/2025.

Positive

• Transaction was tax withholding, not an open-market sale, which reduces potential negative market interpretation
• Reporter retains significant direct ownership (2,429,169 shares) indicating ongoing insider alignment with shareholders
• Filing discloses indirect holdings and trust shares (363,738 indirect; 125,000 in trust), adding transparency

Negative

• None.

Insights

Securities Analyst

TL;DR: Routine tax-withholding disposition, not an open-market sale; insider still holds material equity stake.

The reported disposal of 22,956 shares at $2.48 reflects shares withheld to cover tax obligations upon RSU vesting rather than active selling. Post-transaction direct ownership of 2,429,169 shares and indirect ownership of 363,738 shares indicate continued substantial insider exposure to UPLD equity. This type of Form 4 is typically neutral for market interpretation when clearly documented as tax withholding.

Corporate Governance Expert

TL;DR: Disclosure is consistent with Section 16 reporting; the filing documents appropriate insider action and trust exclusions.

The form accurately discloses the reporter's roles as Director and CEO and specifies the nature of the disposition as tax withholding. The separate disclosure that 125,000 shares held in a trust are excluded from the beneficial ownership calculation provides useful clarity on family trust holdings. Signature by an attorney-in-fact is properly noted with date.

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).

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)
09/16/2025

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	09/16/2025		F(1)		22,956	D	$2.48	2,429,169(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)	09/17/2025
	** 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 did UPLD insider J. McDonald report on 09/16/2025?

The report shows 22,956 shares were withheld to satisfy tax withholding on vested RSUs; this was not an open-market sale.

How many Upland Software shares does J. McDonald beneficially own after the transaction?

After the transaction he beneficially owns 2,429,169 shares directly and 363,738 shares indirectly through National Financial Services.

At what price were the withheld shares reported?

The withheld shares are reported with a price of $2.48 per share.

Are there any additional shares held in trust for Mr. McDonald’s children?

Yes, the filing states 125,000 shares are held in a trust for his children and are excluded from the reported beneficial ownership.

Who signed the Form 4 and when?

The Form 4 is signed by Michael D. Hill as attorney-in-fact for J. McDonald on 09/17/2025.