Upland Software CEO has 1,640 shares withheld

Upland Software’s CEO had shares withheld to cover taxes on RSU vesting, not sold in the market.

Rhea-AI Filing Summary

Upland Software, Inc. (UPLD) reported that CEO and President Nathaniel Sean had 1,640 shares of common stock withheld on September 16, 2026 to satisfy tax withholding obligations upon vesting of restricted stock units. The shares were withheld by the issuer and were not an open market sale. Following this transaction, Sean directly held 48,574 shares of Upland Software common stock. No transactions were made under a Rule 10b5-1 trading plan.

Insider Trade Summary

Tax Withholding: 1,640 shares

Tax Withholding 1 txn

Insider Nathaniel Sean

Role CEO and President

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock F1	1,640	$3.945	$6K

Holdings After Transaction: Common Stock — 48,574 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 taxes: 1,640 shares Per-share value for withholding: $3.945 per share Shares held after transaction: 48,574 shares +2 more

5 metrics

Shares withheld for taxes 1,640 shares Common stock withheld September 16, 2026 to satisfy tax withholding on RSU vesting

Per-share value for withholding $3.945 per share Valuation used for the 1,640 shares withheld for tax obligations

Shares held after transaction 48,574 shares Direct holdings of Upland Software common stock by CEO after withholding

Number of disposition transactions 1 transaction Single tax-withholding disposition reported on this Form 4

Code F shares 1,640 shares Shares reported under code F for payment of tax liability by delivering or withholding securities

Key Terms

restricted stock units, tax withholding obligations, open market sale, Rule 10b5-1

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

"Shares withheld by the issuer to satisfy tax withholding obligations"

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.

Rule 10b5-1 regulatory

"No Rule 10b5-1 trading plan is reported for this transaction"

Rule 10b5-1 is a regulation that allows company insiders to buy or sell their shares at predetermined times, even if they have access to non-public information. It acts like setting a schedule in advance for transactions, helping prevent accusations of unfair trading. This rule provides a way for insiders to plan trades transparently, giving investors confidence that these transactions are not based on hidden information.

FAQ

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

What transaction did UPLD’s CEO report on this Form 4?

CEO and President Nathaniel Sean reported that 1,640 shares of Upland Software common stock were withheld on September 16, 2026 to cover tax withholding obligations related to vesting restricted stock units, rather than being sold in the open market.

Was the UPLD CEO’s Form 4 transaction an open market sale?

No. The filing states the 1,640 shares were withheld by the issuer to satisfy tax withholding obligations upon RSU vesting and that this is not an open market sale of securities.

How many UPLD shares does the CEO hold after this transaction?

After the tax-withholding transaction, CEO Nathaniel Sean directly holds 48,574 shares of Upland Software common stock, as reported in the Form 4.

At what price were the UPLD shares valued for the tax withholding?

The 1,640 shares withheld for tax purposes were valued at $3.945 per share, according to the Form 4 transaction details.

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

No. The Form 4 indicates that no Rule 10b5-1 trading plan is reported for this tax-withholding transaction by Upland Software’s CEO.

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

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Available on EDGAR 09/21/2026 - 05:39 PM Accepted by SEC EDGAR 09/21/2026 - 05:38 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^*

Nathaniel Sean

(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)
	CEO and President

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)		1,640	D	$3.945	48,574	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:

	Sean Nathaniel	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)