Upwork Insider Files Rule 144 to Sell 10,894 Restricted Shares

Rhea-AI Filing Summary

Upwork, Inc. insider notice reports a proposed sale of 10,894 restricted common shares through Morgan Stanley Smith Barney on 09/18/2025 with an aggregate market value of $208,773.71 based on the filing. The filing shows the shares were acquired as restricted stock from the issuer on 09/18/2025. The filer also reported three recent open-market sales by the same person in August 2025 totaling 12,750 shares for gross proceeds of $162,701.01. The issuer has 132,606,579 shares outstanding per the notice.

Insights

Financial Analyst

TL;DR: Routine insider sale notice; size is immaterial relative to total shares outstanding and shows standard liquidity actions.

The Form 144 documents a proposed brokered sale of 10,894 restricted shares via Morgan Stanley, valued at $208,773.71. Compared with 132.6 million shares outstanding, the planned sale represents a de minimis fraction of equity and is unlikely to affect valuation or share liquidity materially. Recent reported August sales totaling 12,750 shares and $162,701.01 in proceeds indicate the insider has been selling modest parcels over the past month. This filing appears to be procedural compliance with Rule 144 rather than a signal of company-specific distress or material news.

Corporate Governance Expert

TL;DR: Compliance-focused filing showing insider liquidation under Rule 144; no disclosed undisclosed material information.

The filer represents under signature that no undisclosed material adverse information is known. The sale is being routed through a registered broker and the securities were reported as restricted stock acquired from the issuer on the same filing date. The filing includes prior open-market dispositions in August, consistent with staged selling. From a governance perspective, documentation of broker, acquisition type, and prior sales meets standard disclosure norms for insider transactions.

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

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	10894	208773.71	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			10894	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
DAVID BOTTOMS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	08/29/2025	1690	25265.50
DAVID BOTTOMS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	08/18/2025	2060	28500.31
DAVID BOTTOMS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	08/08/2025	9000	115936.20

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 Form 144 filed for UPWK disclose?

The filing discloses a proposed sale of 10,894 restricted common shares via Morgan Stanley on 09/18/2025, valued at $208,773.71.

Who is the broker handling the UPWK sale listed in the Form 144?

The broker named in the notice is Morgan Stanley Smith Barney LLC, Executive Financial Services, 1 New York Plaza, 8th Floor, New York, NY 10004.

How many shares outstanding does the Form 144 report for Upwork (UPWK)?

The notice reports 132,606,579 shares outstanding.

Were there any recent insider sales reported in the Form 144 for UPWK?

Yes. The filer reported three August 2025 open-market sales totaling 12,750 shares for gross proceeds of $162,701.01.

What acquisition type is reported for the securities to be sold?

The securities to be sold were acquired as restricted stock from the issuer, with acquisition and payment dates listed as 09/18/2025.