[144] Upwork Inc. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for UPWK: insider sale notice and recent insider transactions. The filing shows a proposed sale of 2,060 common shares through Morgan Stanley Smith Barney with an aggregate market value of $28,500.31 and an approximate sale date of 08/18/2025. The shares are listed as restricted stock acquired on 08/18/2025. The filer, identified in prior sales as David Bottoms, sold 24,312 common shares across four transactions in the past three months, generating gross proceeds totaling $333,270.18. The issuer's number of shares outstanding is reported as 132,606,579, making the planned sale a very small fraction of outstanding shares. The filer certifies no undisclosed material adverse information.

Positive

• Regulatory compliance: Form 144 filed and broker information provided, indicating adherence to disclosure requirements
• Planned sale is small relative to outstanding shares: 2,060 versus 132,606,579 outstanding shares

Negative

• Insider selling activity: 24,312 shares sold in the past three months by the same person, generating $333,270.18 in gross proceeds
• Concentration of past sales: Multiple transactions within a short period may be viewed unfavorably by some investors

Insights

Financial Analyst

TL;DR: Insider plans a modest sale (2,060 shares) after recent larger dispositions totaling 24,312 shares; total proceeds reported $333,270.18.

The filing documents a small proposed sale relative to the company's 132,606,579 shares outstanding, suggesting limited direct market impact from the 2,060-share transaction. However, the cumulative insider sales of 24,312 shares in the prior three months produced $333,270.18 in gross proceeds, indicating meaningful insider liquidity activity. For valuation or modeling purposes, these sales are data points on insider behavior but do not, by themselves, change the company’s financials.

Corporate Governance Expert

TL;DR: Filing indicates compliance with Rule 144 and a representation of no undisclosed material adverse information.

The Form 144 provides required disclosure for an insider sale and includes the signer’s certification regarding undisclosed material information and potential Rule 10b5-1 plan language. The transaction is reported as restricted stock acquired and to be sold on the same date listed, with broker details provided. This transparency supports regulatory compliance; the pattern of recent sales merits monitoring but does not, based solely on this filing, imply governance violations.

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	2060	28500.31	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			2060	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
DAVID BOTTOMS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	08/08/2025	9000	115936.20
DAVID BOTTOMS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	06/18/2025	11562	156148.28
DAVID BOTTOMS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	05/20/2025	1620	26583.39
DAVID BOTTOMS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	05/19/2025	2130	35602.31

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 did the UPWK Form 144 disclose about the proposed sale?

The filing discloses a proposed sale of 2,060 common shares through Morgan Stanley Smith Barney with an aggregate market value of $28,500.31 and an approximate sale date of 08/18/2025.

Who is the seller named in recent UPWK transactions?

Recent sales are attributed to David Bottoms at 530 Lytton Avenue, Palo Alto, CA, with four listed sales in the past three months.

How many shares did the insider sell in the past three months and what were the proceeds?

The insider sold a total of 24,312 common shares on 05/19/2025, 05/20/2025, 06/18/2025, and 08/08/2025, generating gross proceeds of $333,270.18.

What type of shares are being sold according to the Form 144?

The filing indicates the securities to be sold are Common shares and the planned sale arises from restricted stock acquired on 08/18/2025.

Does the filing indicate any undisclosed material adverse information?

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