UPWK Form 144: 22,162 restricted shares notice

Upwork Inc. (symbol UPWK) notice filed on Form 144 reports a proposed sale of 22,162 restricted shares of common stock with an intended sale date of 05/18/2026.

Rhea-AI Filing Summary

Upwork Inc. (symbol UPWK) notice filed on Form 144 reports a proposed sale of 22,162 restricted shares of common stock with an intended sale date of 05/18/2026. The filing also discloses a prior sale of 9,278 shares on 03/18/2026 for $114,228.88.

Insights

Securities Compliance Analyst

Form 144 documents a planned resale of restricted stock and records a recent sale.

Form 144 is a notice required when an affiliate intends to sell restricted or control securities in reliance on Rule 144. The filing lists 22,162 restricted shares with a planned sale date of 05/18/2026, which notifies broker/dealers and the market of an intended transaction.

Prior activity is shown: 9,278 shares sold on 03/18/2026 for $114,228.88. The filing does not state settlement mechanics or whether sales are part of a scheduled plan; subsequent filings may provide additional details.

Key Figures

Proposed shares to be sold: 22,162 shares Shares sold in past 3 months: 9,278 shares Proceeds from prior sale: $114,228.88

3 metrics

Proposed shares to be sold 22,162 shares planned sale date 05/18/2026

Shares sold in past 3 months 9,278 shares sale date 03/18/2026

Proceeds from prior sale $114,228.88 proceeds from 9,278-share sale on 03/18/2026

Key Terms

Restricted Stock, Form 144, Securities To Be Sold

3 terms

Restricted Stock financial

"Securities To Be Sold | Common | 05/18/2026 | Restricted Stock"

Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.

Form 144 regulatory

"Filer Information ... 144: Filer Information"

Form 144 is a document that investors must file with the government when they plan to sell a large number of shares of a company's stock. It helps ensure transparency so everyone knows how many shares are being sold and when, which can impact the stock's price.

Securities To Be Sold regulatory

"144: Securities To Be Sold | Common | 05/18/2026"

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What does the UPWK Form 144 report?

The filing reports a proposed sale of 22,162 restricted shares with an intended sale date of 05/18/2026. It also records a prior sale of 9,278 shares on 03/18/2026 for $114,228.88.

Who is listed as the broker or filer for the UPWK sale?

Morgan Stanley Smith Barney LLC Executive Financial Services is named in the filing as the broker/filer on the Form 144 associated with this notice.

Does the Form 144 confirm the UPWK shares have been sold?

The Form 144 provides notice of an intended sale of 22,162 shares dated 05/18/2026; it does not itself confirm completion of that sale or settlement status.

What proceeds or values are disclosed in the filing?

The filing discloses proceeds of $114,228.88 from a prior sale of 9,278 shares on 03/18/2026. No proceeds are stated for the proposed 22,162-share sale.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 05/18/2026 - 06:46 PM EDT Learn about SEC filing dates

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	0001975669
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	UPWORK INC.
SEC File Number	001-38678
Address of Issuer	530 Lytton Avenue, Suite 301 Palo Alto CALIFORNIA 94301
Phone	(650) 316-7500
Name of Person for Whose Account the Securities are To Be Sold	ERICA GESSERT
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	Officer

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	22162	191998.27	123518137	05/18/2026	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	05/18/2026	Restricted Stock	Issuer			22162	05/18/2026	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	03/18/2026	9278	114228.88

144: Remarks and Signature

Remarks
Date of Notice	05/18/2026
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	/s/ Erica Allen Gessert
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)