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

Rhea-AI Filing Summary

Upland Software (UPLD) reported an insider equity award on a Form 4. A company director acquired 25,000 shares of common stock in the form of restricted stock units (RSUs) on 10/27/2025 at a stated price of $0 per unit.

The RSUs vest as disclosed: one-half on 12/16/2025, with the remainder vesting in two equal quarterly installments on 3/16/2026 and 6/16/2026. Following this transaction, the reporting person beneficially owned 191,437 shares. The ownership form is listed as Direct.

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^*

MAY DAVID

(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
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
10/27/2025

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	10/27/2025		A		25,000(1)	A	$0	191,437	D

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. Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/25 and the remaining shall in two equal quarterly installments on each of 3/16/26 and 6/16/26.

Remarks:

	/s/ Michael D. Hill (as attorney-in-fact for D. May)	10/29/2025
	** 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 report on this Form 4?

A director acquired 25,000 restricted stock units (RSUs) of Upland Software common stock on 10/27/2025.

What is the vesting schedule for the 25,000 RSUs at UPLD?

One-half vests on 12/16/2025, with the remainder vesting in two equal quarterly installments on 3/16/2026 and 6/16/2026.

What was the reported price for the RSUs?

The RSUs were reported at a stated price of $0 per unit.

How many UPLD shares does the reporting person own after the transaction?

Beneficial ownership following the transaction is 191,437 shares.

What is the insider’s relationship to Upland Software (UPLD)?

The reporting person is a Director of Upland Software, Inc.

Is the ownership direct or indirect?

The Form 4 indicates Direct ownership.