Upwork SEC Filings

Upwork CFO Erica Gessert reported multiple transactions on June 18, 2025, involving restricted stock units (RSUs) and common stock:

• Acquired 8,433 RSUs that vest quarterly over four years from June 18, 2024
• Acquired 9,699 RSUs that vest quarterly over four years from June 18, 2025
• Sold 9,267 shares at weighted average price of $13.51 per share in a mandatory "sell to cover" transaction to satisfy tax obligations

Following these transactions, Gessert directly owns 190,738 shares of common stock, plus 92,762 and 145,496 unvested RSUs from two separate grants. The share sale was not discretionary but rather mandated by Upwork's equity incentive plan to cover tax withholding requirements.

Upwork CEO Hayden Brown reported multiple transactions on June 18, 2025, involving the company's common stock and restricted stock units (RSUs):

• Acquired 46,410 shares through the vesting of RSUs (17,733 + 28,677 shares)
• Sold 23,716 shares at an average price of $13.51 to cover tax withholding obligations
• Following these transactions, Brown directly owns 1,153,485 shares
• Maintains 625,228 unvested RSUs (195,066 + 430,162)

The RSUs vest quarterly over four-year periods starting June 18, 2024, and June 18, 2025, respectively. The share sale was mandatory for tax purposes and not a discretionary trade. Brown serves as both Director and President & CEO of Upwork.

Dave Bottoms, GM of Marketplace at Upwork, reported multiple transactions on June 18, 2025, involving Restricted Stock Units (RSUs) and common stock:

• Acquired 20,907 shares through the conversion of RSUs in three tranches: 8,980, 6,023, and 5,904 shares
• Sold 11,562 shares at weighted average price of $13.51 to cover tax withholding obligations
• Retained 9,345 shares after the transactions

The transactions were part of scheduled RSU vestings with different vesting schedules starting from December 2022, June 2024, and June 2025, each vesting quarterly over four years. The share sale was mandatory under Upwork's equity incentive plan for tax withholding through a "sell to cover" transaction, not a discretionary trade by the executive.

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.

Upwork Inc. (UPWK) filed a Form 144 indicating a planned insider sale of 9,267 common shares by Erica Gessert through Morgan Stanley Smith Barney. The proposed sale, valued at roughly $125,154, represents less than 0.01% of the company’s 131.6 million outstanding shares and is scheduled for 18 Jun 2025 on NASDAQ. Form data also shows Gessert sold 19,677 shares for $328,895 on 19 May 2025. The shares to be sold were acquired as restricted stock on the same date as the planned sale, suggesting a routine disposition following vesting. Given the small size relative to float and the absence of additional disclosures, the filing is unlikely to have a material impact on UPWK’s valuation.