[144] Upwork Inc. SEC Filing

Rhea-AI Filing Summary

Upwork Inc. (Form 144) — This notice states that David Bottoms intends to sell 9,000 shares of Common stock through Morgan Stanley Smith Barney LLC on 08/08/2025 on NASDAQ, with an aggregate market value of $115,936.20. The filing reports 132,606,579 shares outstanding, and the 9,000-share block was acquired as restricted stock from the issuer on 06/18/2025.

The form also lists securities sold by the same person during the past three months: 11,562 shares on 06/18/2025 (gross proceeds $156,148.28), 1,620 shares on 05/20/2025 (gross proceeds $26,583.39), 2,130 shares on 05/19/2025 (gross proceeds $35,602.31), and 1,009 shares on 05/15/2025 (gross proceeds $17,294.87). The filer represents there is no undisclosed material adverse information and certifies the truthfulness of the notice.

Positive

• Proposed sale disclosed under Rule 144 with broker, sale date, and aggregate market value specified
• Acquisition details provided: 9,000 shares were acquired as restricted stock from the issuer on 06/18/2025
• Recent insider sales disclosed with dates and gross proceeds for multiple transactions in May–June 2025

Negative

• Insider liquidity activity: the filer sold multiple blocks in the past three months (11,562; 1,620; 2,130; 1,009 shares), which investors may note
• Proposed sale scheduled for 08/08/2025, indicating continued insider disposals in the period

Insights

Securities Analyst

TL;DR: Insider plans a small proposed sale (9,000 shares) relative to outstanding shares; prior small sales are disclosed.

The proposed sale of 9,000 shares at an aggregate reported market value of $115,936.20 represents a de minimis fraction of the 132,606,579 shares outstanding, limiting direct market impact. The filing documents that these shares were acquired as restricted stock on 06/18/2025 and that several small dispositions by the same person occurred in May and June 2025 with listed gross proceeds. From an execution and disclosure standpoint the Form 144 complies with the Rule 144 notice requirements by reporting broker, sale date, and acquisition details.

Corporate Governance Expert

TL;DR: The filing is a routine insider sale notice with required representations; disclosures are specific and include recent sales history.

The notice names the selling person and broker and lists acquisition and payment details (restricted stock acquired 06/18/2025) and recent sales amounts and proceeds. The signer asserts no undisclosed material adverse information. These elements align with transparency expectations for insider transactions, allowing stakeholders to see timing and scale of insider liquidity events without implying any undisclosed issuer issues.

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	9000	115936.20	132606579	08/08/2025	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			9000	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
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
DAVID BOTTOM 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	05/15/2025	1009	17294.87

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 (UPWK) Form 144 disclose about the proposed sale?

The Form 144 states David Bottoms intends to sell 9,000 common shares through Morgan Stanley Smith Barney on 08/08/2025 on NASDAQ, valued at $115,936.20.

When and how were the 9,000 shares being offered acquired?

The filing shows the 9,000 shares were acquired as restricted stock from the issuer on 06/18/2025 and payment is recorded as 06/18/2025.

Has the filer sold other Upwork shares recently?

Yes. The filing lists sales by David Bottoms in the past three months: 11,562 shares on 06/18/2025 (gross proceeds $156,148.28), 1,620 on 05/20/2025 ($26,583.39), 2,130 on 05/19/2025 ($35,602.31), and 1,009 on 05/15/2025 ($17,294.87).

Who is the broker named in the Form 144?

The broker listed for the proposed sale is Morgan Stanley Smith Barney LLC, Executive Financial Services, 1 New York Plaza, 8th Floor, New York, NY 10004.

Does the filer state any undisclosed material adverse information?

The filer represents by signing the notice that they do not know any material adverse information