Upwork SEC Filings

Upwork Inc. (UPWK) filed a Form 4 reporting equity transactions by its Chief Financial Officer. On 11/18/2025, 37,500 restricted stock units (RSUs) vested and were converted into the same number of common shares. These RSUs were part of an award that began vesting 25% on May 18, 2024, with additional vesting in equal quarterly installments.

To cover tax withholding obligations from this vesting, the CFO had 9,059 shares sold at a weighted average price of $16.1382 per share and 9,434 shares sold at a weighted average price of $17.2402 per share under a mandated “sell to cover” arrangement, which the filing states was not a discretionary trade. Following these transactions, the CFO directly owned 237,612 shares of Upwork common stock and held 225,000 RSUs representing contingent rights to receive an equal number of shares.

Upwork Inc. (UPWK) executive GM, Marketplace reported several equity transactions. On November 17, 2025, the reporting person sold 561 shares of common stock at $16.45 per share under a Rule 10b5-1 trading plan. On November 18, 2025, 3,750 restricted stock units (RSUs) were converted into common shares, and the person then sold 955 shares at a weighted average price of $16.1426 and 1,047 shares at a weighted average price of $17.2393. On November 19, 2025, an additional 1,748 shares were sold at a weighted average price of $18.1293.

Some of the sales were required to cover tax withholding obligations tied to RSU vesting, described as “sell to cover” transactions rather than discretionary trades. Following these transactions, the reporting person directly owned 345 shares of Upwork common stock and 18,750 RSUs, each RSU representing one share that vests quarterly over four years beginning on May 18, 2023.

Upwork Inc. reported stronger Q3 2025 results. Revenue rose to $201.7 million from $193.8 million, and net income increased to $29.3 million from $27.8 million. Operating income improved to $29.8 million, supported by lower sales and marketing spend and higher gross profit.

Marketplace revenue was $174.6 million and Enterprise revenue was $27.2 million. Management noted Marketplace take rate increased to 18.9%, reflecting contributions from ads and monetization products. Year to date, operating cash flow reached $184.6 million.

Liquidity remained solid with cash and cash equivalents of $260.8 million and marketable securities of $382.3 million. The company reclassified its $359.3 million convertible senior notes due 2026 to current liabilities. Upwork repurchased 2.1 million shares for $31.0 million in Q3 and 7.3 million shares for $101.9 million year to date; a new $100.0 million authorization was approved in September. Lifted completed two acquisitions: Bubty ($20.4 million) and Ascen ($42.2 million), adding developed technology and customer relationships.

Upwork Inc. furnished an 8-K to announce its financial results for the quarter ended September 30, 2025. The company will host a conference call on November 3, 2025, and the full earnings press release is included as Exhibit 99.1.

The furnished materials are not deemed “filed” under Section 18 of the Exchange Act and are not incorporated by reference except as specifically stated. The release includes certain non-GAAP financial measures, with GAAP reconciliations provided in Exhibit 99.1. Upwork also notes it uses its investor website, blog, and select X/LinkedIn channels to share business and financial updates in line with Regulation FD.

Erica Gessert, Chief Financial Officer of Upwork, Inc. (UPWK), reported multiple equity transactions on 09/18/2025. The filing shows acquisition of 8,433 and 9,700 restricted stock units (RSUs) that vest quarterly over four years, increasing RSU-based claims on common stock. Concurrently, 8,730 shares were sold as a mandatory "sell-to-cover" to satisfy tax-withholding obligations at a weighted-average price of $19.1641 per share. Following these events, the reporting person beneficially owned 218,605, 227,335, and other figures shown per transaction line, and held 84,329 and 135,796 shares attributable to vested RSUs in Table II. The sale was described as required by the company’s equity plan and not a discretionary trade.

Dave Bottoms, GM, Marketplace at Upwork, Inc. (UPWK), reported issuance and sales tied to restricted stock units (RSUs) and a Rule 10b5-1 plan. On 09/18/2025 and 09/19/2025 the reporting person had multiple non-derivative and derivative transactions: vesting RSUs were recorded (8,980; 6,024; 5,904 RSUs) that convert one-for-one into common shares when vested. To satisfy tax-withholding, 10,894 shares were sold on 09/18/2025 at a weighted average price of $19.1646 and 10,014 shares were sold on 09/19/2025 under a 10b5-1 plan at a weighted average price of $19.9588. Following these transactions the reporting person beneficially owned 345 shares (after the 09/19 sale). The RSUs vest quarterly over four years per the stated grant schedules.

Hayden Brown, President & CEO and Director of Upwork, Inc. (UPWK), reported multiple stock transactions in mid-September 2025. The Form 4 shows Rule 10b5-1 plan sales and vesting of restricted stock units (RSUs). On 09/17/2025 she sold 20,000 shares at $18. On 09/18/2025 she sold 20,000 shares at $19 and sold 22,344 shares at a weighted-average $19.1639 after receiving 17,734 and 28,677 vested RSUs that same day. On 09/19/2025 she sold another 20,000 shares at $20. After these transactions, she beneficially owned 1,082,358 shares. The filer adopted the 10b5-1 plan on December 6, 2024, and some sales were "sell to cover" for tax withholding in connection with RSU vesting.

Upwork, Inc. insider filings show a proposed sale of 10,014 common shares (restricted stock units) acquired on 09/18/2025, with an aggregate market value of $196,274.40, to be sold on 09/19/2025 on NASDAQ. The RSUs were granted by the issuer and paid on the acquisition date. The filer has recorded multiple sales of common stock over the prior three months totaling 29,648 shares with combined gross proceeds of $425,480.53 (sales on 08/08/2025, 08/18/2025, 08/29/2025, and 09/18/2025). The notice includes the standard insider representation that no material non-public information is known.

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.