[144] Upwork Inc. SEC Filing

Rhea-AI Filing Summary

Upwork Inc. (UPWK) filed a Form 144 indicating a planned insider sale of 9,267 common shares by Erica Gessert through Morgan Stanley Smith Barney. The proposed sale, valued at roughly $125,154, represents less than 0.01% of the company’s 131.6 million outstanding shares and is scheduled for 18 Jun 2025 on NASDAQ. Form data also shows Gessert sold 19,677 shares for $328,895 on 19 May 2025. The shares to be sold were acquired as restricted stock on the same date as the planned sale, suggesting a routine disposition following vesting. Given the small size relative to float and the absence of additional disclosures, the filing is unlikely to have a material impact on UPWK’s valuation.

Insights

Securities Analyst

TL;DR: Minor insider sale totaling 9.3k shares; immaterial to float, neutral signal.

The Form 144 shows CFO Erica Gessert intends to sell 9,267 shares (~$125k). Combined with a prior 19,677-share sale last month, total disposal over three months is ~29k shares valued at ~$454k—still only 0.02% of shares outstanding. Such volumes are standard for executive liquidity or tax obligations and do not indicate fundamental weakness. No material adverse information is asserted, and no new financial metrics are disclosed. I classify the filing as routine and not impactful for investors.

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	9267	125153.62	131589909	06/18/2025	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	06/18/2025	Restricted Stock	Issuer			9267	06/18/2025	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	05/19/2025	19677	328895.15

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

How many Upwork (UPWK) shares are being registered for sale under this Form 144?

A total of 9,267 common shares are proposed for sale.

What is the aggregate market value of the shares to be sold?

The filing lists an aggregate market value of approximately $125,153.62.

Who is selling the shares and what is their relationship to Upwork?

The seller is Erica Gessert, identified as an insider of Upwork Inc.

When is the planned sale date for these shares?

The anticipated sale date disclosed is 18 June 2025.

How many UPWK shares has the insider sold in the past three months?

In addition to this filing, 19,677 shares were sold on 19 May 2025.