Upwork (NASDAQ: UPWK) CEO lines up another stock sale

Rhea-AI Filing Summary

Upwork, Inc. (UPWK) received a notice that its CEO, Hayden Brown, plans to sell shares under Rule 144. A total of 23,241 common shares are indicated for sale through Morgan Stanley Smith Barney LLC, comprising 7,371 performance shares and 15,870 restricted stock, with a filing date of August 18, 2026. Brown previously sold 23,468 common shares over the prior three months for $191,280.63.

Key Figures

Planned shares to be sold: 23,241 shares Performance shares to be sold: 7,371 shares Restricted stock to be sold: 15,870 shares +3 more

6 metrics

Planned shares to be sold 23,241 shares Common stock listed with Morgan Stanley Smith Barney LLC as of 08/18/2026

Performance shares to be sold 7,371 shares Performance Shares of common stock dated 08/18/2026

Restricted stock to be sold 15,870 shares Restricted Stock of common stock dated 08/18/2026

Shares sold in prior 3 months 23,468 shares Common stock sold on 06/18/2026

Proceeds from prior 3-month sales $191,280.63 Aggregate consideration for 23,468 common shares sold on 06/18/2026

Filing date 08/18/2026 Date associated with current planned sales and signature

Key Terms

Rule 144, Performance Shares, Restricted Stock, Issuer

4 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

Performance Shares financial

"Common | 08/18/2026 | Performance Shares | Issuer"

Performance shares are a type of company stock given to executives or employees that only become theirs if the company meets specific goals, like hitting certain profits or growth targets. They motivate leaders to work toward the company’s success, because their additional shares depend on achieving these results.

Restricted Stock financial

"Common | 08/18/2026 | Restricted Stock | Issuer"

Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.

Issuer regulatory

"Performance Shares | Issuer | | | 7371"

FAQ

What does the Form 144 filing by UPWK’s Hayden Brown disclose?

The filing discloses that Hayden Brown plans to sell 23,241 UPWK common shares under Rule 144 through Morgan Stanley Smith Barney LLC, including both performance shares and restricted stock.

How many UPWK shares is Hayden Brown planning to sell under Rule 144?

Hayden Brown plans to sell 23,241 UPWK common shares. These consist of 7,371 performance shares and 15,870 restricted stock, all referenced with a date of August 18, 2026.

Which broker is handling Hayden Brown’s planned UPWK share sales?

The planned sale of 23,241 UPWK common shares is listed through Morgan Stanley Smith Barney LLC Executive Financial Services, located at 1 New York Plaza, 8th Floor, New York, NY 10004.

What UPWK stock has Hayden Brown sold in the last three months?

Over the prior three months, Hayden Brown sold 23,468 UPWK common shares on June 18, 2026 for aggregate proceeds of $191,280.63, as reported in the sales history section.

What types of UPWK equity awards are included in Hayden Brown’s planned sale?

The planned sale includes 7,371 performance shares and 15,870 restricted stock of UPWK common shares, both identified as issued by the issuer and dated August 18, 2026.

On which market is UPWK common stock related to this Form 144 listed?

The common stock referenced in this Form 144 is listed on NASDAQ, with the securities information table tying the 23,241 common shares to that market as of August 18, 2026.

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

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Available on EDGAR 08/18/2026 - 06:03 PM Accepted by SEC EDGAR 08/18/2026 - 06:03 PM Learn about SEC filing dates

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0001753662
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	UPWORK INC.
SEC File Number	001-38678
Address of Issuer	530 Lytton Avenue, Suite 301 Palo Alto CALIFORNIA 94301
Phone	(650) 316-7500
Name of Person for Whose Account the Securities are To Be Sold	HAYDEN BROWN
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Officer
Relationship to Issuer	Director

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	23241	195821.69	124903365	08/18/2026	NASDAQ

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	08/18/2026	Performance Shares	Issuer			7371	08/18/2026	Not Applicable
Common	08/18/2026	Restricted Stock	Issuer			15870	08/18/2026	Not Applicable

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
HAYDEN BROWN 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	06/18/2026	23468	191280.63

144: Remarks and Signature

Remarks
Date of Notice	08/18/2026
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	/s/ Hayden L. Brown
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)