[8-K] Upwork Inc. Reports Material Event

Rhea-AI Filing Summary

Upwork Inc. announced the appointment of Anthony Kappus as Chief Operating Officer, effective September 2, 2025. Mr. Kappus joins after 11 years at Redfin, where he served in roles including Chief of Digital Revenue and Chief Legal Officer.

His initial compensation includes an annual base salary of $500,000, a target annual bonus equal to 60% of base salary, and a restricted stock unit award equal to $7,250,000 divided by the 30-day average closing price prior to grant. The RSU vests 25% on September 18, 2026 and 6.25% on each quarterly anniversary thereafter. The Severance Agreement provides 12 months base salary and up to 12 months of continued medical premiums if terminated without cause, and in specified change-in-control windows adds a pro-rated bonus and 100% acceleration of then-unvested equity and cash awards (excluding performance-vested awards). The company disclosed no related-party arrangements and furnished a press release as Exhibit 99.1.

Positive

• Experienced hire: Anthony Kappus brings 11 years of senior experience at Redfin, including revenue and legal leadership roles.
• Equity alignment: RSU award valued at $7,250,000 ties a material portion of compensation to shareholder value.
• Clear vesting schedule: RSU vests 25% on September 18, 2026 and 6.25% each quarter thereafter, linking pay to multi-quarter service.
• No related-party conflicts disclosed: Company stated there are no arrangements or family relationships requiring Item 404 disclosure.

Negative

• Change-in-control acceleration: Severance terms provide 100% acceleration of then-unvested equity and cash awards in specified windows, which could accelerate dilution and expense.
• Guaranteed severance: Termination without cause outside change-in-control triggers a lump-sum payment equal to 12 months base salary and up to 12 months of medical premiums.
• Automatic renewals: The Severance Agreement auto-renews for successive three-year terms unless notice is provided, potentially extending protections without fresh approval.

Insights

Corporate Governance Expert

TL;DR: Appointment strengthens operational leadership; governance flags include robust change-in-control acceleration that could lead to dilution or accelerated expense.

The appointment of an experienced senior executive with combined revenue and legal experience introduces operational depth at the C-suite level. Material governance items disclosed include a time-based equity grant valued at $7.25 million (converted to shares at the 30-day average price) and a change-in-control provision that triggers 100% acceleration of then-unvested equity and cash awards in specified windows. Such acceleration is a standard retention feature but is material to shareholders because it can accelerate dilution and expense recognition at or around a transaction. The Severance Agreement term and automatic renewals warrant monitoring from a governance and compensation oversight perspective.

Compensation Analyst

TL;DR: Package mixes moderate cash with a sizable equity award and standard severance; alignment is strong but change-in-control protections are generous.

Economically, the package is composed of a $500,000 base salary, a target annual bonus of 60% of base, and an RSU grant with an initial grant value of $7,250,000 (to be converted into a share count using the 30-day average closing price before grant). Vesting is time-based: 25% after roughly one year and 6.25% quarterly thereafter, which ties long-term retention to service. Severance outside a change-in-control equals 12 months base salary plus up to 12 months of medical premiums. In defined change-in-control windows the package adds a pro-rated bonus and full acceleration of non-performance equity, increasing near-term cost exposure to the company. Overall, the structure aligns incentives but contains material change-in-control protections that affect accounting and potential dilution timing.

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UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

_______________________________________________________

FORM 8-K

_______________________________________________________

CURRENT REPORT

Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): August 12, 2025

_______________________________________________________

UPWORK INC.

(Exact name of Registrant as Specified in Its Charter)

_______________________________________________________

Delaware						001-38678			46-4337682
(State or Other Jurisdiction of Incorporation)						(Commission File Number)			(IRS Employer Identification No.)
530 Lytton Avenue, Suite 301
Palo Alto,			California						94301
(Address of Principal Executive Offices)									(Zip Code)

Registrant’s Telephone Number, Including Area Code: (650) 316-7500

Not Applicable

(Former Name or Former Address, if Changed Since Last Report)

_______________________________________________________

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (see General Instructions A.2. below):

☐    Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐    Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

☐    Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐    Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of Each Class			Trading Symbol			Name of Each Exchange on Which Registered
Common Stock, $0.0001 par value per share			UPWK			The Nasdaq Stock Market LLC

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ¨

Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers.

On August 12, 2025, Upwork Inc., or the Company, announced the appointment of Anthony Kappus, age 45, as its Chief Operating Officer and principal operating officer, effective September 2, 2025. Prior to joining the Company, Mr. Kappus served in a variety of roles over 11 years at Redfin Corporation, including most recently as Chief of Digital Revenue and Chief Legal Officer. Mr. Kappus received a Bachelor of Commerce from the University of Calgary and a J.D. from the University of Washington School of Law.

In connection with Mr. Kappus’s appointment as the Company’s Chief Operating Officer and principal operating officer, Mr. Kappus will receive an initial annual base salary of $500,000. In addition, Mr. Kappus will be eligible to participate in the Company’s bonus plan and will have a target annual bonus of 60% of his base salary. Mr. Kappus will also be granted a restricted stock unit award, or the RSU, under the Company’s 2018 Equity Incentive Plan to acquire such number of shares of the Company’s common stock equal to $7,250,000 divided by the average daily closing price of the Company’s common stock for the 30-day period ending on the trading day immediately prior to the date of grant. The RSU will vest with respect to 25% of the total number of shares subject to the RSU on September 18, 2026 and an additional 6.25% of the total number of shares subject to the RSU shall vest on each quarterly anniversary thereafter, subject to Mr. Kappus’s continued service to the Company on each applicable vesting date.

In addition, Mr. Kappus will enter into a change in control and severance agreement, or the Severance Agreement, that provides for the following benefits if Mr. Kappus is terminated by the Company without cause (as defined in the Severance Agreement) outside of a change in control (as defined in the Severance Agreement) in exchange for a customary release of claims: (i) a lump sum severance payment of 12 months base salary and (ii) payment of premiums for continued medical benefits for up to 12 months.

If Mr. Kappus’s employment is terminated by the Company without cause (as defined in the Severance Agreement) or by him for good reason (as defined in the Severance Agreement) within the three months preceding a change in control (as defined in the Severance Agreement) (but after a legally binding and definitive agreement for a potential change of control has been executed) or within the 12 months following a change in control, the Severance Agreement will provide the following benefits in exchange for a customary release of claims: (i) a lump sum severance payment of 12 months base salary; (ii) a lump sum payment equal to Mr. Kappus’s then-current target bonus opportunity on a pro-rated basis; (iii) 100% acceleration of any then-unvested equity awards and cash-based awards (excluding equity awards that vest, in whole or in part, upon satisfaction of performance criteria); and (iv) payment of premiums for continued medical benefits for up to 12 months. The Severance Agreement will be in effect for three years, with automatic renewals for new three-year periods unless notice is given by the Company to Mr. Kappus at least three months prior to expiration.

There are no arrangements or understandings between Mr. Kappus and any other persons, pursuant to which he was appointed as Chief Operating Officer and principal operating officer, no family relationships among any of the Company’s directors or executive officers and Mr. Kappus, and he has no direct or indirect material interest in any transaction required to be disclosed pursuant to Item 404(a) of Regulation S-K. In connection with his appointment, the Company will enter into its standard form of indemnity agreement, which is attached as Exhibit 10.1 to the Company’s Registration Statement on Form S-1 filed with the Securities and Exchange Commission on September 6, 2018 (File No. 333-227207).

Item 7.01 Regulation FD Disclosure.

On August 12, 2025, the Company issued a press release announcing Mr. Kappus’s appointment as the Company’s Chief Operating Officer. A copy of the press release is attached as Exhibit 99.1 to this Current Report on Form 8-K and is incorporated herein by reference.

The information disclosed in this Item 7.01, including Exhibit 99.1, is being furnished and shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or the Exchange Act, or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference into any other filing under the Securities Act of 1933, as amended, or the Exchange Act except as expressly set forth by specific reference in such a filing.

Item 9.01 Financial Statements and Exhibits.

(d) Exhibits.

Exhibit Number						Description
99.1						Press Release, dated August 12, 2025
104						Cover Page Interactive Data File (embedded within the Inline XBRL document)

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized.

						UPWORK INC.
Date:  August 12, 2025						By:			/s/ Jacob McQuown
									Jacob McQuown VP, Deputy General Counsel

FAQ

Who was appointed Chief Operating Officer at Upwork (UPWK)?

The company appointed Anthony Kappus as Chief Operating Officer, effective September 2, 2025.

What are Mr. Kappus's base salary and target bonus?

His initial base salary is $500,000 with a target annual bonus of 60% of base salary.

How large is the RSU grant and how does it vest?

The RSU equals $7,250,000 divided by the 30-day average closing price prior to grant; it vests 25% on September 18, 2026 and an additional 6.25% on each quarterly anniversary thereafter.

What severance protections are provided to Mr. Kappus?

If terminated without cause outside a change-in-control, he receives a lump sum equal to 12 months base salary plus up to 12 months of medical premium payments; in specified change-in-control windows he also receives a pro-rated bonus and 100% acceleration of then-unvested equity and cash awards (excluding performance-vested awards).

Did the company disclose any related-party transactions with Mr. Kappus?

No. The company stated there are no arrangements or understandings with other persons and no family relationships or material transactions to disclose.