[144] UPWORK, INC SEC Filing

Rhea-AI Filing Summary

Upwork, Inc. (UPWK) insider Hayden L. Brown filed a Form 144 to sell 20,000 common shares through Morgan Stanley Smith Barney LLC, with an aggregate market value of $362,800.00, scheduled approximately for 09/18/2025. The filing shows these shares were originally acquired as PSU/RSU on 06/18/2020. The issuer's outstanding shares are listed as 132,606,579. The notice also discloses three recent sales during the past three months attributed to the same account, including 20,000 shares on 09/17/2025 for $360,000.00, 25,577 shares on 08/18/2025 for $353,862.91, and 60,000 shares on 08/15/2025 for $825,450.00. The filing includes the standard representation regarding absence of undisclosed material information and references reliance on Rule 10b5-1 where applicable.

Positive

• Disclosure completed through a broker (Morgan Stanley Smith Barney LLC) showing transactional transparency
• Use of 10b5-1 plans is indicated for some transactions, suggesting pre-arranged trading and compliance with insider trading frameworks
• Acquisition source documented (PSU/RSU granted 06/18/2020), providing clear provenance of the shares being sold

Negative

• None.

Insights

Securities Compliance Specialist

TL;DR: This is a routine Form 144 insider sale with 10b5-1 activity and standard compliance representations; no new issuer disclosures appear.

The filing identifies Hayden L. Brown as the selling person and documents a proposed sale of 20,000 Upwork common shares through Morgan Stanley Smith Barney LLC on 09/18/2025. The shares were granted as PSU/RSU on 06/18/2020. Multiple prior sales in August and September 2025 are listed, some executed under 10b5-1 plans. The notice contains the required attestation that the seller is not aware of material nonpublic information. From a compliance perspective, the form includes expected elements: broker identification, share counts, acquisition details, and a representation about material information. There are no indications in this filing of procedural deficiencies or missing mandatory fields relevant to Rule 144 disclosure.

Financial Analyst

TL;DR: Insider selling is documented but represents a negligible fraction of outstanding shares; no material impact on capitalization shown.

Aggregating the disclosed transactions in the past three months yields approximately 130,000 shares sold, while the issuer's outstanding share count is 132,606,579, indicating the disclosed sales represent well under one-tenth of one percent of outstanding equity. The specific sale in this Form 144 (20,000 shares, $362,800 market value) is small relative to company size based on the outstanding shares provided. The shares were earned via PSU/RSU awards in 2020, consistent with routine vesting and subsequent disposition. There is no earnings, debt, or operational data in this filing to suggest a material change to Upwork's financial position.

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	362800.00	132606579	09/18/2025	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	06/18/2020	PSU/RSU	Issuer			20000	06/18/2020	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
10b5-1 Sales for HAYDEN L BROWN 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	09/17/2025	20000	360000.00
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

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 filed for UPWK disclose about the sale on 09/18/2025?

The Form 144 discloses a proposed sale of 20,000 Upwork common shares through Morgan Stanley Smith Barney LLC with an aggregate market value of $362,800.00, approximately dated 09/18/2025.

Who is the selling person named in the Form 144 for UPWK?

The filing names Hayden L. Brown as the person for whose account the securities are to be sold.

When were the shares being sold originally acquired according to the filing?

The 20,000 shares were acquired as PSU/RSU on 06/18/2020.

What recent sales by the same account are included in the filing?

The filing lists sales in the past three months: 09/17/2025 20,000 shares for $360,000.00; 08/18/2025 25,577 shares for $353,862.91; and 08/15/2025 60,000 shares for $825,450.00.

How large is this sale relative to Upwork's outstanding shares as reported in the filing?

The filing lists 132,606,579 shares outstanding; the 20,000-share sale represents a de minimis portion of that total.