[144] Upwork Inc. SEC Filing

Rhea-AI Filing Summary

Upwork Inc. (UPWK) Form 144 notice: The filing discloses a proposed sale of 19,036 restricted common shares, with an aggregate market value of $263,364.96, against a reported 132,606,579 shares outstanding. The proposed approximate sale date is 08/18/2025 on NASDAQ. The shares were acquired as restricted stock on 08/18/2025 from the issuer and reported as paid in full on that date. The filer also reported two prior sales by the same person in the last three months: 9,267 shares on 06/18/2025 for $125,153.62 and 19,677 shares on 05/19/2025 for $328,895.15. The notice includes the required representation that the seller is unaware of undisclosed material adverse information.

Positive

• Regulatory compliance: Form 144 properly discloses the proposed sale and recent insider sales, supporting market transparency
• Full disclosure of quantities and values: Proposed sale of 19,036 shares valued at $263,364.96 with two prior sales and dollar amounts provided

Negative

• Insider sales reported: The person has sold or proposes to sell a combined number of shares in recent months (19,677, 9,267, and 19,036), which may be viewed unfavorably by some investors

Insights

Securities Analyst

TL;DR: Routine Rule 144 disclosure showing insider/affiliate sales totaling modest dollar amounts relative to shares outstanding.

The Form 144 notifies the market of a proposed sale of 19,036 restricted shares valued at about $263k, and documents recent sales of 9,267 and 19,677 shares in May and June 2025. For investors, this is a compliance disclosure rather than a financial statement event; the quantities represent a small fraction of the 132.6 million shares outstanding, indicating limited direct impact on capitalization or liquidity. The filing fulfills regulatory transparency requirements and allows market participants to track insider disposition activity.

Corporate Governance Expert

TL;DR: Disclosure aligns with Rule 144 obligations; no evidence in the notice of undisclosed adverse information.

The filing contains the seller's representation that they do not possess undisclosed material adverse information and notes the shares were acquired as restricted stock from the issuer. The inclusion of the seller's prior sales in the past three months improves transparency about recent insider activity. This document is a procedural governance disclosure and does not itself state any governance changes, related-party transactions beyond the restricted grant, or compliance exceptions.

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	19036	263364.96	132606579	08/18/2025	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	08/18/2025	Restricted Stock	Issuer			19036	08/18/2025	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	06/18/2025	9267	125153.62
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

What does Upwork's (UPWK) Form 144 disclose?

The Form 144 discloses a proposed sale of 19,036 restricted common shares valued at $263,364.96, with prior sales of 9,267 and 19,677 shares in June and May 2025.

When is the proposed sale date on the UPWK Form 144?

The approximate date of sale listed is 08/18/2025 on NASDAQ.

How many shares outstanding does the filing report for UPWK?

The filing reports 132,606,579 shares outstanding.

How were the shares acquired according to the Form 144?

The 19,036 shares were acquired as restricted stock from the issuer and payment is noted as completed on 08/18/2025.

Does the filer represent possession of undisclosed material information?

Yes, by signing the notice the person represents they do not know any material adverse information about the issuer that has not been publicly disclosed.