[144] Upwork Inc. SEC Filing

Rhea-AI Filing Summary

Upwork Inc. (Ticker: UPWK) – Form 144 filing (Rule 144 proposed insider sale)

The notice discloses that an insider plans to sell 11,562 common shares of Upwork Inc. through Morgan Stanley Smith Barney on or about 18 June 2025 on Nasdaq. The broker estimates an aggregate market value of $156,148.28, implying an average price of roughly $13.51 per share. Compared with the company’s stated 131,589,909 shares outstanding, the proposed sale represents approximately 0.009 % of the float, indicating a relatively immaterial dilution impact.

Recent trading history reported in the filing shows the same insider, David Bottoms, has already disposed of 14,352 shares across four transactions between 19 March 2025 and 20 May 2025, generating $208,613.72 in gross proceeds. If the new sale is executed, cumulative dispositions over the three-month window will reach 25,914 shares (≈0.020 % of shares outstanding) for total proceeds of roughly $364,762.

The filer certifies that no non-public material adverse information is known and that the sale complies with Rule 144 requirements. No additional financial performance data, corporate developments, or earnings information are included in this filing.

Positive

• Sale size is immaterial—11,562 shares represent only about 0.009 % of total shares outstanding, limiting dilution and market impact.
• Regulatory compliance: The insider uses Form 144 and certifies unawareness of material non-public information, indicating adherence to disclosure rules.

Negative

• Continued insider selling trend: Including past 3-month activity, insider dispositions total 25,914 shares, which may be viewed as a bearish sentiment indicator, albeit small in scale.

Insights

Securities Analyst

TL;DR: Small-scale Rule 144 insider sale; negligible dilution, but adds to recent selling trend.

The proposed 11.6 k-share sale—less than 0.01 % of Upwork’s outstanding shares—poses minimal supply pressure. However, when combined with the 14.3 k shares already sold since March, it extends a pattern of insider disposition that some investors may interpret as a sentiment headwind. The dollar amounts remain modest relative to Upwork’s market cap, so valuation impact should be limited. The Rule 144 disclosure and the filer’s certification lower regulatory risk; no operational or financial metrics are provided, so the filing is not an earnings signal. Overall, I view the news as slightly negative but low impact.

Corporate Governance Expert

TL;DR: Routine, compliant Form 144; insider diversifying holdings, limited governance concern.

From a governance perspective, the filing evidences proper adherence to SEC Rule 144 and includes the seller’s representation of no undisclosed adverse information. Sale size is immaterial and executed through a reputable broker, suggesting standard liquidity management rather than a strategic exit. Investors should note the clustering of sales within a quarter, but the aggregate level remains too small to raise red-flag governance issues. Accordingly, I deem the event neutral in governance terms.

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	11562	156148.28	131589909	06/18/2025	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	06/18/2025	Restricted Stock	Issuer			11562	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	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
DAVID BOTTOMS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	03/19/2025	9593	129133.15

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

How many Upwork (UPWK) shares does the insider intend to sell?

The Form 144 lists 11,562 common shares to be sold.

What is the estimated market value of the proposed UPWK share sale?

Aggregate market value is $156,148.28 according to the filing.

When is the proposed sale of UPWK shares expected to occur?

The filing cites an approximate sale date of 18 June 2025.

How many Upwork shares were already sold by the insider in the last three months?

The filing details 14,352 shares sold between 19 March 2025 and 20 May 2025.

What percentage of Upwork’s outstanding shares does the new sale represent?

The 11,562 shares equal roughly 0.009 % of the 131,589,909 shares outstanding.

Which broker will handle the sale of the UPWK shares?

The proposed sale will be executed through Morgan Stanley Smith Barney LLC.