Upwork officer plans sale of 9,336 shares

Officer Erica Allen Gessert filed a Rule 144 notice to sell 9,336 UPWK common shares, following sales of 22,844 shares over the prior three months.

Rhea-AI Filing Summary

UPWORK, INC (UPWK) was notified that officer Erica Allen Gessert intends to sell 9,336 shares of its common stock under Rule 144 through Morgan Stanley Smith Barney LLC, with a stated approximate aggregate market value of $78,897.60 as of September 18, 2026 on NASDAQ.

The shares to be sold are described as restricted stock held by the issuer’s officer, and the notice also reports that Gessert sold 22,844 shares of common stock during the prior three months for an aggregate sale price of $192,476.69.

Key Figures

Proposed shares to be sold: 9,336 shares Approximate aggregate market value of proposed sale: $78,897.60 CUSIP or security identifier: 124903365 +3 more

6 metrics

Proposed shares to be sold 9,336 shares Common stock proposed for sale under Rule 144 as of September 18, 2026

Approximate aggregate market value of proposed sale $78,897.60 Value of 9,336 UPWK common shares in the planned Rule 144 sale

CUSIP or security identifier 124903365 Identifier associated with the UPWK common stock listed in the securities information

Shares sold in past 3 months 22,844 shares UPWK common stock sold on August 18, 2026 by Erica Gessert

Aggregate proceeds from past 3-month sale $192,476.69 Sale of 22,844 shares of UPWK common stock on August 18, 2026

Date of proposed Rule 144 sale September 18, 2026 Date tied to the proposed sale of 9,336 UPWK shares

Key Terms

Rule 144, restricted stock, aggregate market value, Issuer

4 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

restricted stock financial

"Common | 09/18/2026 | Restricted Stock | Issuer"

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.

aggregate market value financial

"Common | Morgan Stanley Smith Barney LLC ... | 9336 | 78897.60"

Aggregate market value is the combined price you would pay to buy all outstanding shares of a company or all companies in a group at current market prices — essentially the sum of each stock’s market capitalization. It matters to investors because it shows the overall size and weight of an investment or sector (like the total cost to buy every piece of a puzzle), helps compare scale across companies or markets, and influences index composition and risk exposure.

Issuer regulatory

"Restricted Stock | Issuer"

FAQ

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

What does the Form 144 filing by UPWK officer Erica Gessert disclose?

It discloses that officer Erica Allen Gessert intends to sell 9,336 shares of UPWK common stock under Rule 144, with an approximate aggregate market value of $78,897.60 as of September 18, 2026, through Morgan Stanley Smith Barney LLC on NASDAQ.

How many UPWK shares has Erica Gessert sold in the last three months?

The notice reports that 22,844 shares of UPWK common stock were sold on August 18, 2026 for an aggregate sale price of $192,476.69 during the past three months.

What type of UPWK securities are covered by this Form 144 filing?

The filing covers common stock of UPWORK, INC that is described as restricted stock, with 9,336 shares proposed to be sold under Rule 144 as of September 18, 2026.

Which broker is handling the planned UPWK share sale under Form 144?

The proposed sale of 9,336 UPWK common shares is to be executed through Morgan Stanley Smith Barney LLC Executive Financial Services, located at 1 New York Plaza, 8th Floor, New York, NY 10004.

On which market are the UPWK shares in this Form 144 intended to be sold?

The Form 144 states that the 9,336 shares of UPWK common stock covered by the notice are to be sold on NASDAQ as of September 18, 2026.

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

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Available on EDGAR 09/18/2026 - 04:31 PM Accepted by SEC EDGAR 09/18/2026 - 04:31 PM 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	9336	78897.60	124903365	09/18/2026	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	09/18/2026	Restricted Stock	Issuer			9336	09/18/2026	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	08/18/2026	22844	192476.69

144: Remarks and Signature

Remarks
Date of Notice	09/18/2026
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)