Toast, Inc. CRO Jonathan Vassil Exercises and Sells 14,280 Shares Under 10b5-1 Plan

Insider Filing Analysis: Toast, Inc. ($TOST)

Executive Summary

On September 2, 2026, Jonathan Vassil, Chief Revenue Officer of Toast, Inc., exercised stock options to acquire 14,280 shares of Class A Common Stock at $2.21 per share and subsequently sold all 14,280 shares at weighted average prices between $33.542 and $34.095. The aggregate sale proceeds totaled $484,056.30.

Transaction Details

• Option Exercise: 14,280 shares exercised at $2.21 per share (Code M).
• Sale Tranche 1: 5,100 shares sold at a weighted average price of $33.542 (range: $32.945 to $33.940).
• Sale Tranche 2: 9,180 shares sold at a weighted average price of $34.095 (range: $33.950 to $34.260).
• Total Shares Sold: 14,280 shares at an effective average price of ~$33.90.
• Holdings After Transaction:
  • Direct: 69,966 Class A Common shares and 285,871 remaining derivative stock options.
  • Indirect: 84,269 Class A Common shares held by The Jonathan S. Vassil Grantor Retained Annuity Trust #1.

Regulatory and Contextual Factors

• Rule 10b5-1 Plan: The transactions were conducted pursuant to a pre-arranged Rule 10b5-1 trading plan adopted on March 13, 2026.
• Significance: Low. The activity represents a standard option exercise and sale under an established automated trading plan without discretionary timing.