Upwork insider sold 109,293 shares recently; 20,000 more planned

Rhea-AI Filing Summary

Upwork, Inc. insider sale notice: This Form 144 shows an intended sale of 20,000 common shares by a person for whose account the securities are to be sold, through Morgan Stanley Smith Barney on 09/17/2025, with an aggregate market value of $342,000.00. The shares were originally acquired as Restricted and Performance Stock Units on 11/18/2022. The filing also discloses three recent sales by the same person totaling 109,293 shares with gross proceeds of $1,499,606.98, including an explicit Rule 10b5-1 plan sale of 60,000 shares on 08/15/2025. Outstanding shares noted are 132,606,579.

Positive

• Disclosure compliance: The filer submitted a Form 144 with required details for the proposed sale.
• Use of 10b5-1 plan: One sale (60,000 shares on 08/15/2025) was executed under a documented 10b5-1 plan, indicating preplanned trading.

Negative

• Insider selling activity: Recent sales total 109,293 shares, which may be noted by investors even if small versus outstanding shares.

Insights

Securities Analyst

TL;DR: Insider plans a modest sale of 20,000 shares; several recent dispositions including a 10b5-1 sale were disclosed.

The filing documents a routine Rule 144 notice for the proposed sale of 20,000 common shares valued at $342,000, acquired as RSUs/PSUs in 2022. Recent transactions show aggregate dispositions of 109,293 shares over three dates, including a 10b5-1 plan sale of 60,000 shares, which indicates preplanned execution rather than opportunistic trading. Relative to the 132.6 million shares outstanding, these amounts are small in percentage terms, so the market-cap impact is likely limited. Disclosure is complete and compliant with Rule 144 requirements.

Corporate Governance Expert

TL;DR: Filing reflects transparent insider selling with representation of no undisclosed material information.

The filer certifies no undisclosed material adverse information and notes reliance on a 10b5-1 plan for at least one sale, which supports procedural compliance. The origin of the sold shares as Restricted/Performance Stock Units is stated, providing necessary context on acquisition. From a governance standpoint, the filing meets statutory disclosure norms; the volume sold versus shares outstanding is small, suggesting limited governance concern, though concentrated insider activity over a short period merits routine investor attention to subsequent disclosures.

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

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

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

Relationship to Issuer

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	20000	342000.00	132606579	09/17/2025	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	11/18/2022	Restricted and Performance Stock Units	Issuer			20000	11/18/2022	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 L BROWN 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	08/18/2025	25577	353862.91
10b5-1 Sales for HAYDEN L BROWN 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	08/15/2025	60000	825450.00
HAYDEN L BROWN 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	06/18/2025	23716	320294.07

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What does the Form 144 for UPWK disclose?

The form discloses a proposed sale of 20,000 common shares on 09/17/2025 valued at $342,000.00, acquired as RSUs/PSUs on 11/18/2022.

How many shares did the insider recently sell and for how much?

The filing lists three sales totaling 109,293 shares with combined gross proceeds of $1,499,606.98 on dates 06/18/2025, 08/15/2025 (10b5-1), and 08/18/2025.

Were any sales executed under a Rule 10b5-1 plan?

Yes. The filing explicitly shows a 10b5-1 sale of 60,000 shares on 08/15/2025.

What was the acquisition origin of the shares to be sold?

The 20,000 shares proposed for sale were acquired as Restricted and Performance Stock Units from the issuer on 11/18/2022.

How many shares outstanding does the issuer report?

The filing lists 132,606,579 shares outstanding for the issuer.