Toast CRO Jonathan Vassil Exercises Options and Sells Shares via 10b5-1 Plan

Executive Summary

On October 5, 2026, Toast, Inc. ($TOST) filed a Form 4 for Chief Revenue Officer Jonathan Vassil, detailing transactions occurring on October 1 and October 2, 2026. The filings encompass quarterly RSU vesting, mandatory tax-withholding share dispositions, and an exercise-and-sell transaction executed pursuant to a pre-established Rule 10b5-1 trading plan.

Key Transaction Breakdown

• RSU Vesting & Settlement (October 1, 2026):
  • Vested and acquired an aggregate of 14,266 shares of Class A Common Stock across four tranches (4,748; 4,987; 3,430; and 1,101 shares).
• Tax Withholding Disposition (October 2, 2026):
  • Sold 6,808 shares of Class A Common Stock at $29.354 per share ($199,842.03 total) to satisfy mandatory tax obligations associated with the RSU settlements.
• Option Exercise and 10b5-1 Sale (October 2, 2026):
  • Exercised stock options to acquire 6,657 shares at an exercise price of $2.21 per share.
  • Simultaneously sold the 6,657 shares at a volume-weighted average price of $30.032 (ranging from $30.00 to $30.10) for gross proceeds of $199,923.02, pursuant to a Rule 10b5-1 plan adopted on March 13, 2026.

Post-Transaction Holdings

• Direct Ownership: 77,424 shares of Class A Common Stock.
• Indirect Ownership: 84,269 shares held via The Jonathan S. Vassil Grantor Retained Annuity Trust #1.
• Derivative Holdings Remaining: 89,124 unvested RSUs across various grant dates and 279,214 vested stock options exercisable at $2.21 expiring April 21, 2030.

Market & Trading Significance

The trading activity is assessed as Low Significance. The sales were non-discretionary (a tax-related sell-to-cover and a scheduled 10b5-1 option exercise/sale) and do not signal a shift in executive sentiment regarding Toast, Inc.'s operational outlook.