Upland Software (UPLD) CEO has shares withheld to cover tax bill

Filing Impact

(Neutral)

Filing Sentiment

(Neutral)

Form Type

Rhea-AI Filing Summary

Upland Software, Inc. CEO and President Nathaniel Sean reported a routine tax-related share disposition. On 2026-06-16, 18,605 shares of common stock were withheld by the company to cover tax obligations from vesting restricted stock units, at $0.6064 per share. This was explicitly described as not being an open market sale. After the withholding, Sean directly held 502,146 shares of Upland Software common stock.

Insider Trade Summary

1 transaction reported

Mixed 1 txn

Insider Nathaniel Sean

Role CEO and President

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock	18,605	$0.6064	$11K

Holdings After Transaction: Common Stock — 502,146 shares (Direct, null)

Footnotes (1)

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Key Figures

Shares withheld for taxes: 18,605 shares Tax withholding share value: $0.6064 per share Shares held after transaction: 502,146 shares

3 metrics

Shares withheld for taxes 18,605 shares Tax withholding on RSU vesting, 2026-06-16

Tax withholding share value $0.6064 per share Valuation used for withheld shares

Shares held after transaction 502,146 shares CEO direct ownership after tax withholding

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

"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.

Form 4 regulatory

"This Form 4 reports a tax-withholding disposition by the CEO."

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.

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Form 4 Insider Transactions: What Each Field Means →

06/16/2026 - 06:33 PM

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)
06/16/2026

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	06/16/2026		F⁽¹⁾		18,605	D	$0.6064	502,146	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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

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:

	/s/ Michael D. Hill (as attorney-in-fact for S. Nathaniel)	06/16/2026
	** 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)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transaction did Upland Software (UPLD) report in this Form 4?

Upland Software reported that CEO Nathaniel Sean had 18,605 common shares withheld to cover tax obligations from vesting restricted stock units. This was a tax-withholding disposition, not a market sale, and is part of routine equity compensation administration.

Was the Upland Software (UPLD) CEO’s Form 4 transaction an open market sale?

No, the filing states the shares were withheld by Upland Software to satisfy tax withholding obligations on vesting restricted stock units. The footnote clarifies this is not an open market sale of securities, but a non-market tax payment mechanism.

How many Upland Software (UPLD) shares were withheld for the CEO’s taxes?

The Form 4 shows that 18,605 shares of Upland Software common stock were withheld. These shares covered tax liabilities triggered by the vesting of restricted stock units and did not involve selling shares into the open market.

What is the Upland Software (UPLD) CEO’s shareholding after this Form 4 event?

Following the tax-withholding transaction, CEO Nathaniel Sean directly held 502,146 shares of Upland Software common stock. This figure reflects his position after 18,605 shares were withheld by the issuer to satisfy equity award-related tax obligations.

At what price were Upland Software (UPLD) shares valued for the tax withholding?

The withheld shares were valued at $0.6064 per share for tax purposes. This price applies to the 18,605 shares used to satisfy the CEO’s tax obligations associated with vesting restricted stock units, as disclosed in the Form 4 filing.