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

Rhea-AI Filing Summary

Upland Software director and CEO J. McDonald reported an insider sale of 14,438 shares of common stock on 09/11/2025 at a weighted average price of $2.3593 per share. The filing shows 2,452,125 shares held directly after the sale and 363,738 shares held indirectly through National Financial Services as custodian for J. McDonald. The filer says the sales were made to recognize general portfolio tax savings and that the price reflects multiple trades between $2.31 and $2.43. The filing excludes 125,000 shares held in a trust for his children.

Positive

• Transparent disclosure of weighted average sale price and price range ($2.31 to $2.43).
• Reason for sale provided: "general portfolio tax savings," reducing likelihood of signaling company-specific negative information.
• Post-transaction holdings disclosed: 2,452,125 direct shares and 363,738 indirect shares, aiding investor clarity.

Negative

• Insider sale reported: 14,438 shares disposed, which may be noted by some investors even if immaterial.
• No evidence of a 10b5-1 plan was indicated, so timing rationale rests solely on the stated tax purpose.

Insights

Financial Analyst

Insider sale is small relative to total holdings and appears tax-driven, not a signal of material company change.

The sale of 14,438 shares against total direct beneficial ownership of 2,452,125 shares represents a de minimis reduction (well under 1%). The filing provides a clear reason: "general portfolio tax savings," and discloses a weighted average sale price of $2.3593 executed across multiple trades between $2.31 and $2.43. No derivative transactions or other unusual dispositions are reported. From a financial perspective, this is a routine Section 16 sale without material impact on outstanding shares or corporate capital structure.

Corporate Governance Expert

Disclosure is compliant and sufficiently detailed for an 16(a) sale, including execution price range and trustee-held exclusions.

The Form 4 lists the reporting person's roles as both director and CEO and confirms timely reporting of the sale date and aggregated post-transaction holdings. The explanation notes multiple trade prices and offers to provide further breakdown upon request, which aligns with best practices for transparency. The filing also clarifies indirect holdings and trust assets excluded from beneficial ownership totals. There are no indications of rule 10b5-1 plan reliance in this filing.

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)
09/11/2025

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	09/11/2025		S(1)		14,438	D	$2.3593(2)	2,452,125(3)	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. Sales made to recognize general portfolio tax savings.

2. This transaction was executed in multiple trades at prices ranging from $2.31 to $2.43. The price reported above reflects the weighted average sale price. The Reporting Person undertakes to provide upon request by the staff of the Securities and Exchange Commission, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate sale price.

3. 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)	09/11/2025
	** 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 J. McDonald (UPLD) report on Form 4 filed 09/11/2025?

He reported a sale of 14,438 shares of Upland common stock executed on 09/11/2025 at a weighted average price of $2.3593.

How many UPLD shares does J. McDonald beneficially own after the reported transaction?

The filing shows 2,452,125 shares held directly after the sale and 363,738 shares held indirectly through National Financial Services.

Why were the shares sold according to the Form 4?

The reporting person states the sales were made to recognize general portfolio tax savings.

What price range were the shares sold at in the UPLD Form 4?

The transaction was executed in multiple trades at prices ranging from $2.31 to $2.43, with a weighted average of $2.3593.

Are there any shares held in trust that are excluded from the beneficial ownership total?

Yes. The filing states it does not include 125,000 shares of common stock held in a trust for Mr. McDonald's children for which The Bryn Mawr Trust Company of Delaware is trustee.