Upland Software CFO has 1,117 shares withheld

Upland Software’s CFO had shares withheld to cover RSU tax obligations, leaving her with 28,883 directly held shares.

Rhea-AI Filing Summary

Upland Software, Inc. (UPLD) reported that its Chief Financial Officer Jennifer L. Simon had 1,117 shares of common stock withheld on September 16, 2026 to satisfy tax withholding obligations related to vesting of restricted stock units. After this withholding, she directly holds 28,883 shares of Upland common stock. The company notes this was not an open market sale of securities.

Insider Trade Summary

Tax Withholding: 1,117 shares

Tax Withholding 1 txn

Insider Simon Jennifer L.

Role Chief Financial Officer

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock F1	1,117	$3.945	$4K

Holdings After Transaction: Common Stock — 28,883 shares (Direct)

Footnotes (1)

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.

Key Figures

Shares withheld for tax: 1,117 shares Price per share for tax withholding: $3.945 per share Shares held after transaction: 28,883 shares

3 metrics

Shares withheld for tax 1,117 shares Shares withheld on September 16, 2026 to satisfy tax withholding obligations on RSU vesting

Price per share for tax withholding $3.945 per share Valuation used for the 1,117 shares withheld on September 16, 2026

Shares held after transaction 28,883 shares CFO Jennifer L. Simon’s directly held Upland common shares after the tax-withholding transaction

Key Terms

restricted stock units, tax withholding obligations, open market sale, Form 4

4 terms

restricted stock units financial

"in connection with the vesting of restricted stock units"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

tax withholding obligations financial

"to satisfy tax withholding obligations in connection with the vesting"

open market sale financial

"This is not an open market sale of securities"

An open market sale is when a company or a shareholder sells shares through the regular stock market to any willing buyer, using ordinary exchange trading rather than private deals. It matters to investors because it increases the number of shares available and can push the price down or change ownership balance—think of it like someone putting extra items on a supermarket shelf for any shopper to buy, which can lower the item's price if supply suddenly grows.

Form 4 regulatory

"according to a Form 4 filing"

Form 4 is a official document that company insiders, such as executives or major shareholders, file with regulators whenever they buy or sell company shares. It provides transparency about how those with inside knowledge are trading, helping investors see if insiders are confident in the company's prospects or may be selling for personal reasons. This information can influence investor decisions by revealing insiders' perspectives on the company's value.

FAQ

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

What insider transaction did UPLD report for CFO Jennifer L. Simon?

Upland Software reported that CFO Jennifer L. Simon had 1,117 shares of common stock withheld on September 16, 2026 to satisfy tax withholding obligations tied to vesting restricted stock units, according to a Form 4 filing.

Was the UPLD CFO’s September 16, 2026 transaction an open market sale?

No. The footnote states the 1,117 shares were withheld by Upland Software to satisfy tax withholding obligations upon RSU vesting and that this was not an open market sale of securities.

How many UPLD shares does the CFO hold after this Form 4 transaction?

After the September 16, 2026 withholding, CFO Jennifer L. Simon directly holds 28,883 shares of Upland Software common stock, as reported in the Form 4 filing.

What price per share is associated with the UPLD CFO’s withheld shares?

The 1,117 shares withheld to satisfy tax obligations are reported at $3.945 per share in the Form 4, which is used to value the tax-withholding disposition.

Was the UPLD CFO’s Form 4 transaction under a Rule 10b5-1 trading plan?

The Form 4 indicates no Rule 10b5-1 plan is reported; the document-level checkbox for such a plan is marked false, and the footnote describes only tax-related share withholding on RSU vesting.

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

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Available on EDGAR 09/21/2026 - 05:38 PM Accepted by SEC EDGAR 09/21/2026 - 05:37 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^*

Simon Jennifer L.

(Last) (First) (Middle)

900 S. CAPITAL OF TEXAS HWY

LAS CIMAS IV, SUITE 300

(Street)

AUSTIN TEXAS 78746

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Upland Software, Inc. [ UPLD ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
09/16/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	09/16/2026		F(1)		1,117	D	$3.945	28,883	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. 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.

Remarks:

	Jennifer Simon	09/21/2026
	** 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.
* Form 4: SEC 1474 (03-26)