[144] UPWORK, INC SEC Filing

Rhea-AI Filing Summary

Insider sale notice for UPWK common stock. The filing reports a proposed sale of 20,000 shares through Morgan Stanley Smith Barney with an aggregate market value of $392,000, with an approximate sale date of 09/19/2025 on NASDAQ. The shares were acquired as Restricted and Performance Stock Units on 06/18/2020. The filing also discloses multiple recent sales by or for Hayden L. Brown during Aug–Sep 2025 totaling 147,921 shares and generating gross proceeds of $2,347,515.56 across listed transactions. The filer certifies no undisclosed material adverse information and references reliance on Rule 10b5-1 trading instructions where applicable.

Positive

• None.

Negative

• Insider selling concentration: Recent disclosures show 147,921 shares sold in Aug–Sep 2025, which could be viewed negatively by some investors.
• Material context missing in excerpt: The provided content omits issuer name and filer CIK fields, limiting independent verification from this excerpt.

Insights

Financial Analyst

TL;DR: Significant insider selling via 10b5-1 and open notice may exert modest near-term pressure on the stock.

The filing shows an additional planned sale of 20,000 shares and documents prior sales totaling 147,921 shares for the same insider over the past month. The shares originated from Restricted and Performance Stock Units granted in June 2020, indicating these are not open-market purchases but disposition of long-held equity compensation. Aggregate recent gross proceeds of approximately $2.35 million are disclosed across several transactions. For investors, the activity is a clear signal of insider liquidity events rather than an operational disclosure; its market impact depends on trade size relative to daily volume and overall float, which are not provided in this filing.

Corporate Governance Expert

TL;DR: The filing is a routine Rule 144/10b5-1 disclosure documenting compliance with insider-sale procedures.

The notice identifies the sales as likely executed under a Rule 10b5-1 plan or instructions and includes the required representation that the seller has no undisclosed material information. The securities were granted as restricted and performance units in 2020, which is common for executive compensation. The filing provides required broker and transaction details but omits issuer name and filer CIK in the provided excerpt; those omissions in this excerpt limit external verification but may be present in the full submission. From a governance standpoint, the disclosure meets standard form content by listing past sales and planned dispositions.

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

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	20000	392000.00	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	06/18/2020	Restricted and Performance Stock Units	Issuer			20000	06/18/2020	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
10b5-1 Sales for HAYDEN L BROWN 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	09/18/2025	20000	380000.00
HAYDEN L BROWN 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	09/18/2025	22344	428202.65
10b5-1 Sales for HAYDEN L BROWN 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	09/17/2025	20000	360000.00
HAYDEN L BROWN 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	08/18/2025	25577	353862.91
10b5-1 Sales for HAYDEN L BROWN 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	08/15/2025	60000	825450.00

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 are being offered in the UPWK Form 144?

The notice proposes sale of 20,000 common shares with an aggregate market value of $392,000.

Who is the seller named in the filing for UPWK?

The disclosed seller is Hayden L. Brown, with multiple recent transactions listed under his name and 10b5-1 sales.

When were the shares being sold originally acquired?

The shares were acquired as Restricted and Performance Stock Units on 06/18/2020.

Were there recent sales by the same person before this notice?

Yes. The filing lists several sales in Aug–Sep 2025 totaling 147,921 shares with gross proceeds of $2,347,515.56.

Through which broker will the 20,000 shares be sold?

The broker listed is Morgan Stanley Smith Barney LLC, Executive Financial Services, New York, NY.