Insider sells 9,044 common shares

UPWK insider sale reported: Erica Gessert sold 9,044 common shares on 12/18/2025 for $186,196.97.

Rhea-AI Filing Summary

UPWK insider sale reported: Erica Gessert sold 9,044 common shares on 12/18/2025 for $186,196.97.

The filing also lists securities to be sold on 02/18/2026: 12,742 restricted stock and 13,550 performance shares, each labeled Issuer.

Insights

Securities Compliance Officer

Routine Form 144 sale notification by an insider; proceeds and planned issuer-held share dispositions are recorded.

The filing documents a reported sale of 9,044 common shares on 12/18/2025 for $186,196.97. It also lists planned dispositions dated 02/18/2026 of 12,742 restricted stock and 13,550 performance shares identified as Issuer.

Regulatory treatment and timing follow standard resale notice procedures; cash‑flow treatment and final settlement timing are not stated in the excerpt. Subsequent filings or broker confirmations would show execution details.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What did the UPWK Form 144 report about Erica Gessert?

The Form 144 reports that Erica Gessert sold 9,044 common shares on 12/18/2025, receiving $186,196.97. The filing also lists planned issuer-designated shares to be sold on 02/18/2026.

How many shares and what proceeds were disclosed in the sale?

The filing discloses a sale of 9,044 common shares with proceeds of $186,196.97. The transaction date shown is 12/18/2025 as reported in the Form 144 excerpt.

What securities are listed as "to be sold" on the filing?

The excerpt lists securities to be sold on 02/18/2026: 12,742 restricted stock and 13,550 performance shares, both identified in the table with the designation Issuer.

Does the filing state who handled the sale or broker details?

The excerpt lists Morgan Stanley Smith Barney LLC with an address at 1 New York Plaza, 8th Floor, New York, NY 10004, which is shown under securities/broker information in the Form 144 excerpt.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 02/18/2026 - 04:35 PM Learn about SEC filing dates

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	0001975669
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	UPWORK INC.
SEC File Number	001-38678
Address of Issuer	530 Lytton Avenue, Suite 301 Palo Alto CALIFORNIA 94301
Phone	(650) 316-7500
Name of Person for Whose Account the Securities are To Be Sold	ERICA GESSERT
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	Officer

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	26292	363376.84	130380213	02/18/2026	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	02/18/2026	Restricted Stock	Issuer			12742	02/18/2026	Not Applicable
Common	02/18/2026	Performance Shares	Issuer			13550	02/18/2026	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
ERICA GESSERT 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	12/18/2025	9044	186196.97

144: Remarks and Signature

Remarks
Date of Notice	02/18/2026
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	/s/ Erica Allen Gessert
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)