UPWORK, INC SEC Filings

Upwork, Inc.’s GM & Chief Operating Officer Anthony Ray Kappus reported RSU vesting on July 18, 2026, converting 1,412 RSUs into the same number of common shares at no cost. To satisfy tax withholding from this vesting, 558 shares were automatically sold in a required “sell to cover” transaction at a weighted average price of $9.0554 per share. After the transaction, he reported holding 21,191 RSUs that vest in equal quarterly installments over four years beginning July 18, 2026, subject to continued employment.

Upwork Inc. reports that, effective July 14, 2026, its chief financial officer and principal financial officer, Erica Gessert, has taken a temporary medical leave. The company currently anticipates that she will return to her role during the fourth quarter of 2026.

During this leave, President and Chief Executive Officer Hayden Brown will serve as interim principal financial officer. The company states there is no arrangement or understanding under which she was selected, no relevant family relationships or related-party interests, and she will receive no additional compensation or changes to existing plans for assuming the interim role.

UPWORK, INC Chief Financial Officer Erica Gessert reported routine equity compensation activity involving RSUs and a related tax sale. On June 18 2026, 18,132 restricted stock units converted into the same number of common shares. To cover tax withholding on this vesting, 9,169 common shares were sold in a mandated “sell to cover” transaction at a weighted average price of $8.1507 per share, with actual sale prices ranging from $8.02 to $8.25 per share. The filing notes this sale did not represent a discretionary trade by Gessert. Following these transactions, she directly holds 341,609 shares of Upwork common stock. The RSU awards continue to vest in equal quarterly installments over four years beginning on June 18, 2024 and June 18, 2025, subject to her continued employment.

Upwork, Inc. Chief Accounting Officer Sabrina Mekhalfa reported routine equity transactions tied to restricted stock units (RSUs). She exercised RSUs covering 3,577 units, receiving the same number of common shares at a $0.00 exercise price. On the same date, 1,276 common shares were sold at a weighted average price of $8.1509 per share to cover tax withholding obligations under the company’s equity incentive plans, described as a mandatory “sell to cover” transaction rather than a discretionary trade. Following these transactions, she directly holds 4,396 shares of Upwork common stock.

Upwork, Inc. President & CEO Hayden Brown reported routine equity compensation activity involving restricted stock units (RSUs) and a related tax sale. On June 18, 2026, Brown sold 23,468 shares of common stock at a weighted average price of $8.1507 per share to cover tax withholding obligations tied to RSU vesting, as required by the company’s “sell to cover” election and not as a discretionary trade.

On the same date, Brown also acquired 46,411 shares of common stock through the vesting and settlement of RSUs. Following these transactions, she directly holds 797,495 shares of Upwork common stock and continues to hold additional unvested RSUs subject to quarterly vesting over four-year schedules.

Upwork Inc. entered into a new secured revolving credit facility with a syndicate of lenders led by Bank of America. The Credit Facility allows borrowings of up to $150.0 million, including a $10.0 million sublimit for standby letters of credit, with an option to increase total commitments by up to an additional $50.0 million. It matures on June 23, 2029 and is secured by substantially all assets of Upwork and its domestic subsidiaries.

Borrowings will bear interest at either Term SOFR plus a margin of 2.00%–2.50% or a Base Rate plus a margin of 1.00%–1.50%, depending on Upwork’s consolidated net leverage ratio. Proceeds may be used for working capital, general corporate purposes, repurchasing or repaying certain existing convertible debt, transaction fees and expenses, and potential acquisitions, in each case subject to the facility’s terms. The agreement includes customary financial covenants and events of default under which lenders may terminate the facility and accelerate repayment.

Upwork Inc. reported a Form 144 notice indicating proposed sales of restricted common stock by an insider. The filing lists 23,468 shares identified as restricted stock with a sale/notice date of 06/18/2026. The filing also records two prior sales on 05/18/2026 of 22,546 and 50,000 shares, with dollar amounts shown.

Morgan Stanley Smith Barney LLC Executive Financial Services filed a Form 144 reporting a proposed sale of 9,169 shares of Common (Restricted Stock) on 06/18/2026. The filing also lists a prior sale: Erica Gessert sold 22,162 shares on 05/18/2026 for $191,998.27. The securities are listed with NASDAQ as the exchange in the excerpt.

BRAMLEY CLAIRE reported acquisition or exercise transactions in this Form 4 filing.

Upwork, Inc. director Claire Bramley received an equity award in the form of 45,146 restricted stock units (RSUs) of common stock. The RSUs vest in three equal installments: one-third on June 4, 2027, one-third on June 4, 2028, and the final third on the earlier of the date immediately prior to Upwork’s 2029 annual stockholders’ meeting or December 31, 2029, in each case conditioned on continued service.