[144] UPWORK, INC SEC Filing

Rhea-AI Filing Summary

Upwork, Inc. insider filings show a proposed sale of 10,014 common shares (restricted stock units) acquired on 09/18/2025, with an aggregate market value of $196,274.40, to be sold on 09/19/2025 on NASDAQ. The RSUs were granted by the issuer and paid on the acquisition date. The filer has recorded multiple sales of common stock over the prior three months totaling 29,648 shares with combined gross proceeds of $425,480.53 (sales on 08/08/2025, 08/18/2025, 08/29/2025, and 09/18/2025). The notice includes the standard insider representation that no material non-public information is known.

Positive

• Disclosure of planned sale under Rule 144 provides transparency to the market
• RSUs were acquired and paid on 09/18/2025, showing clear provenance of the shares

Negative

• Insider selling activity totaling 29,648 shares in three months could be perceived negatively by some investors
• Filing lacks context on proportion of insider holdings, limiting assessment of materiality

Insights

Securities Analyst

TL;DR: Insider is selling recent RSUs and has executed several recent sales; transaction size is modest relative to large-cap market caps.

The filing documents a routine Rule 144 notice for 10,014 RSUs acquired and to be sold the following day, indicating a planned disposition rather than an atypical corporate event. Prior dispositions over the past three months total 29,648 shares and roughly $425k in proceeds, consistent with staged selling of equity compensation. There is no disclosure here of material non-public information or changes to corporate fundamentals. Impact on capital structure or liquidity is immaterial given typical public float sizes for Nasdaq-listed issuers.

Corporate Governance Expert

TL;DR: Filing appears to be a routine insider sale under Rule 144 and includes the requisite attestation.

The notice records acquisition via restricted stock units and subsequent planned sale, with the signer attesting to absence of undisclosed material information and referencing Rule 10b5-1 where applicable. The pattern of multiple scheduled sales suggests compliance with personal liquidity planning or 10b5-1 arrangements rather than event-driven exits. No governance red flags or regulatory issues are evident from the disclosed details alone.

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	10014	196274.40	132606579	09/19/2025	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	09/18/2025	Restricted Stock Units	Issuer			10014	09/18/2025	N/A

* 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 Ave, Suite 301 Palo Alto CA 94301	Common	09/18/2025	10894	208773.71
10b5-1 Sales for DAVID TIMOTHY BOTTOMS 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	08/29/2025	1690	25265.50
DAVID BOTTOMS 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	08/18/2025	2060	28504.22
DAVID BOTTOMS 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	08/08/2025	9000	115937.10

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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 shares is the Upwork (UPWK) insider planning to sell?

The filing notifies a proposed sale of 10,014 common shares (restricted stock units) scheduled for 09/19/2025 on NASDAQ.

When were the shares being sold by the insider acquired?

The RSUs were acquired and paid on 09/18/2025, with the issuer listed as the source.

How much value do the proposed shares represent?

The aggregate market value of the 10,014 shares is reported as $196,274.40.

Has the insider sold other Upwork shares recently?

Yes. The filer sold 9,000 shares on 08/08/2025, 2,060 on 08/18/2025, 1,690 on 08/29/2025, and 10,894 on 09/18/2025, totaling 29,648 shares and $425,480.53 in gross proceeds.

Does the filing indicate any undisclosed material information about Upwork?

The signer represents they do not know any material adverse information about the issuer that is not publicly disclosed.