UPWK Form 144: Erica Gessert Proposed Sale and Recent Disposition

Rhea-AI Filing Summary

Form 144 notice for Upwork, Inc. (UPWK) reports a proposed sale of 8,730 common shares through Morgan Stanley Smith Barney on NASDAQ with an aggregate market value of $167,302.59. The filer indicates those shares were acquired as restricted stock from the issuer and the acquisition and proposed sale are both dated 09/18/2025. The filing also discloses a prior sale by the same person, Erica Gessert, of 19,036 shares on 08/18/2025 for gross proceeds of $263,364.96. The document contains the broker name and the total shares outstanding reported as 132,606,579. The standard signature representation affirms no undisclosed material adverse information.

Insights

Securities Analyst

TL;DR: Insider sale notice for 8,730 shares; small relative size versus outstanding shares, routine disclosure.

The Form 144 shows a proposed sale of 8,730 Upwork common shares through Morgan Stanley Smith Barney with market value of $167,302.59, and indicates those shares were restricted stock acquired from the issuer on the same date as the proposed sale. The filing also lists a recent prior sale of 19,036 shares by Erica Gessert on 08/18/2025 for $263,364.96. Compared with the reported 132,606,579 shares outstanding, the disclosed transactions constitute an immaterial percentage of the float. This is a routine Rule 144 notification documenting compliance with resale limitations and brokered sale arrangements.

Corporate Governance Expert

TL;DR: Notice documents compliance with resale rules; contains required representations but no new company disclosures.

The filing includes the mandatory representation that the seller is unaware of undisclosed material adverse information and notes the transaction uses a registered broker-dealer. The acquisition row states the shares were granted as restricted stock by the issuer and paid on 09/18/2025, which is relevant to lock-up and holding-period calculations under Rule 144. There are no indications of unusual terms or contingent consideration disclosed. From a governance standpoint, this filing fulfills disclosure obligations without revealing material corporate developments.

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	8730	167302.59	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			8730	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
ERICA GESSERT 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	08/18/2025	19036	263364.96

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?

It discloses a proposed sale of 8,730 Upwork common shares through Morgan Stanley Smith Barney on NASDAQ with an aggregate market value of $167,302.59.

Who is the seller named in the filing and did they sell other shares recently?

The filing names Erica Gessert and also reports she sold 19,036 shares on 08/18/2025 for gross proceeds of $263,364.96.

How many shares does Upwork report outstanding in the filing?

The filing reports 132,606,579 shares outstanding, which provides context for the size of the proposed sale.

What type of acquisition is reported for the shares to be sold?

The 8,730 shares were acquired as restricted stock from the issuer with acquisition and payment dates listed as 09/18/2025.

Which broker is handling the proposed sale?

Morgan Stanley Smith Barney LLC is listed as the broker for the proposed sale.