Toast (TOST) CRO Vassil Jonathan Exercises Options, Sells Shares

What Happened
Vassil Jonathan, Chief Revenue Officer of Toast, exercised 14,280 options (fully vested) on 2026-09-02 and acquired those shares at $2.21 each (cost $31,559). He immediately sold 14,280 shares in two open-market transactions the same day — 5,100 shares at a weighted average $33.54 (proceeds $171,064) and 9,180 shares at a weighted average $34.09 (proceeds $312,992) — for total gross proceeds of about $484,056. The filing also reports a derivative conversion/disposition entry at $0.00 related to the exercise.

Key Details

• Transaction date: 2026-09-02 (reported on Form 4 filed 2026-09-04) — filing appears timely.
• Exercise: 14,280 shares acquired at $2.21 each; total cost reported $31,559. (Transaction code M)
• Sales: 5,100 shares sold at weighted avg $33.54 (footnote: sales ranged $32.945–$33.940) and 9,180 shares sold at weighted avg $34.09 (footnote: sales ranged $33.95–$34.26). Total proceeds ≈ $484,056. (Transaction code S)
• Footnotes: Sales were executed under a Rule 10b5-1 trading plan adopted March 13, 2026 (F1). Seller offers to provide breakdown of shares sold at each price within the reported ranges (F2, F3). Options were fully vested as of the exercise (F4).
• Shares owned after the transactions: not disclosed in the provided excerpt of the filing.

Context

• This pattern — exercising vested options and selling the resulting shares the same day — is effectively a cash-out of option value (commonly reported as an exercise followed by open-market sales). The separate $0.00 derivative disposition entry reflects the conversion/settlement of the derivative instrument and is reported alongside the exercise.
• Sales under a pre-established 10b5-1 plan are routine and permit scheduled trading; they do not by themselves indicate insider sentiment about the company.