[144] UPWORK, INC SEC Filing

Rhea-AI Filing Summary

Upwork, Inc. Form 144 filing: This notice reports a proposed sale of 22,344 shares of Upwork common stock by an affiliated person, to be executed through Morgan Stanley Smith Barney LLC on 09/18/2025 with an aggregate market value of $428,202.65 based on the filing. The securities are described as restricted stock acquired from the issuer on 09/18/2025 and the filing indicates prior sales by the same person, Hayden Brown, totaling 103,577 shares across three transactions in the past three months, generating gross proceeds of $1,539,310.36. The filer certifies no undisclosed material adverse information.

Positive

• None.

Negative

• Insider selling concentration: The filing and recent transactions show 103,577 shares sold in the past three months plus a proposed sale of 22,344 shares.
• Material proceeds disclosed: Recent gross proceeds reported total $1,539,310.36, indicating sizable dispositions by the same person.

Insights

Securities Analyst

TL;DR: Significant insider sales reported; cumulative recent dispositions exceed 100k shares and may be noticed by investors.

The filing shows a proposed sale of 22,344 restricted shares to be executed through a major brokerage on 09/18/2025 valued at $428,202.65 and discloses three recent sales by Hayden Brown totaling 103,577 shares in the prior three months with gross proceeds of $1,539,310.36. These figures are explicit in the filing and represent material insider disposition activity relative to an individual holder. The filing contains no financial performance data or forward-looking commentary; assessment should be limited to the mechanics and scale of the sales disclosed.

Corporate Governance Expert

TL;DR: The Form 144 documents compliant disposition activity but raises governance questions about insider selling cadence.

The notice indicates the securities were acquired as restricted stock from the issuer and that sales are being routed via Morgan Stanley Smith Barney LLC. The signer affirms no material nonpublic information exists. From a governance perspective, the filing is procedural and complies with Rule 144 disclosure requirements; however, repeated sales by the same person within a short period are notable to stakeholders monitoring insider transactions. The filing itself contains no assertions beyond sale mechanics and certification.

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	22344	428202.65	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	09/18/2025	Restricted Stock	Issuer			22344	09/18/2025	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	09/17/2025	20000	360000.00
HAYDEN BROWN 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	08/18/2025	25577	353860.36
HAYDEN BROWN 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	08/15/2025	60000	825450.00

144: Remarks and Signature

Remarks

Date of Notice

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 UPWK Form 144 filed on 09/18/2025 report?

The filing reports a proposed sale of 22,344 shares of Upwork common stock via Morgan Stanley Smith Barney LLC on 09/18/2025 with an aggregate market value of $428,202.65.

Who sold shares disclosed in the Form 144 for UPWK?

The filing and related recent-sales table identify Hayden Brown as the seller for recent transactions and as the person associated with the proposed sale.

How many shares did Hayden Brown sell in the past three months according to the filing?

The filing discloses three sales on 09/17/2025 (20,000 shares), 08/18/2025 (25,577 shares), and 08/15/2025 (60,000 shares), totaling 105,577 shares sold in those listed transactions and a proposed additional 22,344 shares.

What proceeds were generated by the recent sales disclosed in the Form 144?

The gross proceeds reported for the three recent sales are $360,000.00, $353,860.36, and $825,450.00, totaling $1,539,310.36.

Were the securities to be sold acquired as a gift or purchased?

The filing states the securities to be sold were acquired as restricted stock from the issuer and lists the acquisition and payment date as 09/18/2025.