Upwork insider plans sale of 23,893 shares

Hayden Brown files a Rule 144 notice to resell 23,893 shares of UPWK common stock, following earlier sales in August 2026.

Available on EDGAR 09/18/2026 - 04:23 PM EDT Accepted by SEC EDGAR 09/18/2026 - 04:23 PM EDT Learn about SEC filing dates

Rhea-AI Filing Summary

UPWORK, INC (UPWK) is the issuer for a planned resale of common stock under Rule 144 by Hayden Brown through Morgan Stanley Smith Barney. The notice covers 23,893 shares of common stock, with an aggregate market value of $201,917.35, and lists prior sales in the past three months.

Key Figures

Shares proposed to be sold under Rule 144: 23,893 shares Aggregate market value of shares in notice: $201,917.35 CUSIP: 124903365 +5 more

8 metrics

Shares proposed to be sold under Rule 144 23,893 shares Common stock covered by the current Form 144 notice

Aggregate market value of shares in notice $201,917.35 Market value of 23,893 UPWORK, INC common shares

CUSIP 124903365 CUSIP for UPWORK, INC common stock in this notice

Proposed transaction date September 18, 2026 Planned date for sales under this Form 144

Shares sold August 18, 2026 (first transaction) 23,241 shares Common stock sold for $195,821.69 in prior 3 months

Proceeds from August 18, 2026 (first transaction) $195,821.69 Sale of 23,241 common shares

Shares sold August 18, 2026 (second transaction) 50,000 shares Common stock sold for $421,355.00 in prior 3 months

Proceeds from August 18, 2026 (second transaction) $421,355.00 Sale of 50,000 common shares

Key Terms

Rule 144, Restricted Stock, aggregate market value, 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.

Restricted Stock financial

"Common | 09/18/2026 | 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.

aggregate market value financial

"Common | ... | 201917.35 | 124903365"

Aggregate market value is the combined price you would pay to buy all outstanding shares of a company or all companies in a group at current market prices — essentially the sum of each stock’s market capitalization. It matters to investors because it shows the overall size and weight of an investment or sector (like the total cost to buy every piece of a puzzle), helps compare scale across companies or markets, and influences index composition and risk exposure.

Issuer regulatory

"Restricted Stock | Issuer"

FAQ

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

What does the Form 144 filing disclose for UPWK?

The Form 144 filing discloses that 23,893 shares of UPWORK, INC (UPWK) common stock, with an aggregate market value of $201,917.35, may be sold under Rule 144 for the account of Hayden Brown through Morgan Stanley Smith Barney.

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

Hayden Brown’s notice covers the potential sale of 23,893 shares of UPWORK, INC common stock, as indicated in the Form 144 securities information section.

What is the aggregate market value of the UPWK shares in this Form 144?

The aggregate market value of the UPWORK, INC common shares covered by this Form 144 notice is $201,917.35, based on the information provided in the securities section.

Which broker is listed for the planned UPWK share sales?

The broker listed for the planned UPWORK, INC share sales is Morgan Stanley Smith Barney LLC Executive Financial Services, located at 1 New York Plaza, 8th Floor, New York, NY 10004.

What UPWK shares has Hayden Brown sold in the past three months?

In the past three months, Hayden Brown reported selling 23,241 shares of UPWORK, INC common stock for $195,821.69 and 50,000 shares for $421,355.00, both on August 18, 2026.

When is the proposed sale date for the UPWK shares in this Form 144?

The proposed transaction date for the UPWORK, INC common shares covered by this Form 144 notice is September 18, 2026, as listed in the securities information and securities to be sold sections.

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

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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	23893	201917.35	124903365	09/18/2026	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	09/18/2026	Restricted Stock	Issuer			23893	09/18/2026	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	08/18/2026	23241	195821.69
HAYDEN BROWN 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	08/18/2026	50000	421355.00

144: Remarks and Signature

Remarks
Date of Notice	09/18/2026
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)