Upwork (NASDAQ: UPWK) officer to sell 22,844 shares of stock

Rhea-AI Filing Summary

Upwork, Inc. (UPWK) is the issuer for a planned sale of common stock by officer Erica Gessert under Rule 144. The notice covers up to 22,844 common shares, with an indicated transaction value of $192,476.69, to be sold through Morgan Stanley Smith Barney LLC, with an earliest sale date of 08/18/2026. In the prior three months, Gessert sold 9,169 common shares on 06/18/2026 for proceeds of $74,733.77.

Key Figures

Planned shares to be sold: 22,844 shares Indicated value of planned sale: $192,476.69 Earliest sale date: 08/18/2026 +2 more

5 metrics

Planned shares to be sold 22,844 shares Common stock covered by the Rule 144 notice

Indicated value of planned sale $192,476.69 Value associated with the 22,844 Upwork common shares

Earliest sale date 08/18/2026 Date when the Rule 144 shares may first be sold

Shares sold in prior 3 months 9,169 shares Common stock sold on 06/18/2026

Proceeds from prior 3-month sale $74,733.77 Value of 9,169 common shares sold on 06/18/2026

Key Terms

Rule 144, Restricted Stock, Securities To Be Sold, Executive Financial Services

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 | 08/18/2026 | 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.

Securities To Be Sold financial

"144: Securities To Be Sold"

Executive Financial Services financial

"Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza"

FAQ

What insider sale is being reported for Upwork Inc. (UPWK)?

An officer of Upwork, Erica Gessert, has filed a notice to sell up to 22,844 common shares of Upwork stock. The planned sale is under Rule 144 and is scheduled no earlier than 08/18/2026 through Morgan Stanley Smith Barney LLC.

How many Upwork (UPWK) shares may Erica Gessert sell and what is the value?

The notice covers up to 22,844 common shares of Upwork with an indicated value of $192,476.69. These shares are to be sold as restricted stock under Rule 144, through Morgan Stanley Smith Barney LLC’s Executive Financial Services group.

When can the reported Upwork (UPWK) Rule 144 sale begin?

The earliest sale date disclosed is 08/18/2026. This date marks when the covered 22,844 Upwork common shares may first be sold under Rule 144, subject to its volume and other conditions for resales of restricted or control securities.

What Upwork (UPWK) stock sales has Erica Gessert made in the last three months?

In the prior three months, 9,169 common shares of Upwork were sold on 06/18/2026 for $74,733.77. These past sales are disclosed to show aggregate trading activity required to be reported in connection with Rule 144 resale limitations.

Through which broker will the Upwork (UPWK) shares be sold?

The planned sale of 22,844 Upwork common shares will be handled by Morgan Stanley Smith Barney LLC, Executive Financial Services, at 1 New York Plaza, New York. This broker acts as the intermediary for the Rule 144 restricted stock transaction.

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

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Available on EDGAR 08/18/2026 - 05:29 PM Accepted by SEC EDGAR 08/18/2026 - 05:28 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	22844	192476.69	124903365	08/18/2026	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	08/18/2026	Restricted Stock	Issuer			22844	08/18/2026	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	06/18/2026	9169	74733.77

144: Remarks and Signature

Remarks
Date of Notice	08/18/2026
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)