Upwork (UPWK) insider plans $409K stock sale in August 2026

Rhea-AI Filing Summary

UPWORK, INC (UPWK) received a notice under Rule 144 that Hayden Brown intends to sell up to 50,000 shares of Upwork common stock through Morgan Stanley Smith Barney LLC. The proposed sale has an indicated aggregate market value of about $409,500.00 based on recent prices and a planned sale date of 08/18/2026.

The shares to be sold were acquired upon the vesting of restricted stock units and performance stock units during the period from 02/18/2024 through 05/18/2024. Upwork reports approximately 124,903,365 shares of common stock outstanding. In the prior three months, Hayden Brown sold 23,468 shares for proceeds of $191,280.63.

Key Figures

Planned shares to be sold: 50,000 shares Indicated aggregate market value: $409,500.00 Shares outstanding: 124,903,365 shares +4 more

7 metrics

Planned shares to be sold 50,000 shares Common stock to be sold by Hayden Brown under Rule 144

Indicated aggregate market value $409,500.00 Estimated value of 50,000 shares proposed for sale

Shares outstanding 124,903,365 shares Approximate UPWK common shares outstanding

Planned sale date 08/18/2026 Expected date of the proposed Rule 144 sale

Shares sold in past 3 months 23,468 shares UPWK common shares sold on 06/18/2026

Proceeds from past 3-month sales $191,280.63 Value of 23,468 shares sold on 06/18/2026

RSU/PSU vesting period 02/18/2024–05/18/2024 Period during which units vested and shares were acquired

Key Terms

Rule 144, restricted stock units, performance stock units, Form 144

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 units financial

"acquired upon the vesting of restricted stock units and performance 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.

performance stock units financial

"acquired upon the vesting of restricted stock units and performance stock units"

Performance stock units are a type of company award that grants employees shares of stock only if certain performance goals are met. They motivate employees to work toward specific company achievements, aligning their interests with those of shareholders. For investors, they can influence a company's future stock supply and reflect management’s confidence in reaching key targets.

Form 144 regulatory

"144: Securities To Be Sold"

Form 144 is a document that investors must file with the government when they plan to sell a large number of shares of a company's stock. It helps ensure transparency so everyone knows how many shares are being sold and when, which can impact the stock's price.

FAQ

What does the Form 144 filing disclose for UPWK and Hayden Brown?

The filing states that Hayden Brown plans to sell up to 50,000 UPWK common shares under Rule 144, with an indicated aggregate value of $409,500.00, and that prior three-month sales totaled 23,468 shares.

How many UPWK shares does Hayden Brown plan to sell under this Form 144?

Hayden Brown plans to sell up to 50,000 shares of UPWK common stock. The shares are expected to be sold through Morgan Stanley Smith Barney LLC, with an estimated total value of $409,500.00 based on the referenced market price.

What is the approximate market value of the UPWK shares to be sold?

The intended sale of 50,000 UPWK shares has an indicated aggregate market value of about $409,500.00. This value is based on the market price reference used in the notice for the planned sale dated 08/18/2026.

How many UPWK shares are outstanding according to this Form 144?

The notice reports that approximately 124,903,365 shares of UPWK common stock are outstanding. This figure provides context for the planned 50,000-share sale under Rule 144 as a small portion of total shares.

What prior UPWK stock sales by Hayden Brown are disclosed in this Form 144?

The filing notes that on 06/18/2026, Hayden Brown sold 23,468 UPWK common shares for proceeds of $191,280.63. These transactions are reported as securities sold during the past three months, as required by Rule 144.

How were the UPWK shares being sold by Hayden Brown acquired?

The shares were acquired upon the vesting of restricted stock units (RSUs) and performance stock units (PSUs) during the period from 02/18/2024 through 05/18/2024, according to the remarks section of the notice.

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Available on EDGAR 08/18/2026 - 04:27 PM Accepted by SEC EDGAR 08/18/2026 - 04:26 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 Ave, Suite 301 Palo Alto CALIFORNIA 94301
Phone	6503167500
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	Director
Relationship to Issuer	Officer

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	50000	409500.00	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	02/18/2024	RSU/PSU	Issuer			50000	02/18/2024	N/A

* 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 Ave, Suite 301 Palo Alto CA 94301	Common	06/18/2026	23468	191280.63

144: Remarks and Signature

Remarks	The securities to be sold were acquired upon the vesting of restricted stock units and performance stock units during the period of 02/18/2024 through 05/18/2024.
Date of Notice	08/18/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	11/19/2025
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 Brown
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)