Toast (NYSE: TOST) CRO sells 4,700 shares under Rule 10b5-1 plan
Rhea-AI Filing Summary
Toast, Inc. Chief Revenue Officer Jonathan Vassil exercised stock options for 4,700 shares of Class A Common Stock on August 5, 2026, at exercise prices of $17.3800 and $17.3300 per share, then sold 4,700 shares at a weighted average of $36.0230 under a Rule 10b5-1 trading plan adopted on March 13, 2026; following these transactions, a grantor retained annuity trust associated with him held 84,269 shares indirectly.
Positive
- None.
Negative
- None.
Insider Trade Summary 10b5-1
Exercise and Sale: 4,700 shares ($88K approx. pre-tax spread)
Exercise and Sale
6 txns
Insider
Vassil Jonathan
Role
Chief Revenue Officer
Sold
4,700 shs ($169K)
Approx. gross sale proceeds
$169K
Approx. exercise cost
$82K
Approx. pre-tax spread
$88K
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Option (Right to Buy) F1, F3 | 2,000 | $0.00 | $0.00 |
| Exercise | Stock Option (Right to Buy) F1, F4 | 2,700 | $0.00 | $0.00 |
| Exercise | Class A Common Stock F1 | 2,000 | $17.38 | $35K |
| Exercise | Class A Common Stock F1 | 2,700 | $17.33 | $47K |
| Sale | Class A Common Stock F2 | 4,700 | $36.023 | $169K |
| holding | Class A Common Stock | -- | -- | -- |
Holdings After Transaction:
Stock Option (Right to Buy) — 478,839 shares (Direct);
Class A Common Stock — 69,966 shares (Direct);
Class A Common Stock — 84,269 shares (Indirect, The Jonathan S. Vassil Grantor Retained Annuity Trust #1)
Footnotes (4)
- F1. This transaction was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 13, 2026.
- F2. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $36 to $36.26 inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the Staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within this price range set forth in this footnote.
- F3. The shares subject to this option are fully vested and exercisable as of the date hereof.
- F4. The shares underlying this option shall vest and become exercisable in sixteen equal quarterly installments following April 1, 2023.
Key Figures
Shares sold: 4,700 shares
Sale price: $36.0230 per share
Options exercised (grant 1): 2,000 shares at $17.3800
+3 more
6 metrics
Shares sold
4,700 shares
Class A Common Stock sold on August 5, 2026
Sale price
$36.0230 per share
Weighted average sale price with trades from $36.00 to $36.26
Options exercised (grant 1)
2,000 shares at $17.3800
Stock Option (Right to Buy) expiring March 15, 2032, fully vested
Options exercised (grant 2)
2,700 shares at $17.3300
Stock Option (Right to Buy) expiring March 10, 2033, vesting in 16 quarterly installments
Indirect holdings after transactions
84,269 shares
Class A Common Stock held by The Jonathan S. Vassil Grantor Retained Annuity Trust #1
10b5-1 plan adoption date
March 13, 2026
Date Jonathan Vassil adopted the Rule 10b5-1 trading plan
Key Terms
Rule 10b5-1 trading plan, weighted average price, Grantor Retained Annuity Trust, Stock Option (Right to Buy)
4 terms
Rule 10b5-1 trading plan regulatory
"This transaction was effected pursuant to a Rule 10b5-1 trading plan..."
A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.
weighted average price financial
"The reported price in Column 4 is a weighted average price."
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
Grantor Retained Annuity Trust financial
"The Jonathan S. Vassil Grantor Retained Annuity Trust #1"
A grantor retained annuity trust (GRAT) is an estate-planning tool where the person who creates the trust transfers assets into it but receives fixed cash payments (an annuity) from the trust for a set number of years; whatever remains after that term passes to designated beneficiaries. It matters to investors because it can shift future appreciation of assets out of the creator’s taxable estate—like putting an asset into a timed vending machine that pays you fixed amounts while any extra value that grows inside the machine goes to heirs with reduced gift or estate tax consequences.
Stock Option (Right to Buy) financial
"security_title: Stock Option (Right to Buy)"
AI-generated analysis. How Rhea-AI works. Not financial advice.
FAQ
What insider transactions did Toast (TOST) CRO Jonathan Vassil report?
He exercised options for 4,700 shares and sold 4,700 shares of Toast Class A Common Stock on August 5, 2026. The option exercises were at $17.3800 and $17.3300 per share, and the sale used a weighted average price of $36.0230.
Were Jonathan Vassil’s Toast (TOST) transactions under a Rule 10b5-1 plan?
Yes. The transactions were effected under a Rule 10b5-1 trading plan adopted by Jonathan Vassil on March 13, 2026. This plan-based structure means the exercises and sale followed a pre-established schedule rather than discretionary timing decisions.
What stock options did the Toast (TOST) CRO exercise in this Form 4?
He exercised two stock option grants covering 2,000 and 2,700 shares at exercise prices of $17.3800 and $17.3300, respectively. One option was already fully vested, while the other vests in sixteen equal quarterly installments starting April 1, 2023.
What is the nature of Jonathan Vassil’s indirect Toast (TOST) holdings?
His indirect holdings are reported through The Jonathan S. Vassil Grantor Retained Annuity Trust #1, which holds 84,269 Toast Class A shares. The Form 4 identifies this trust as the indirect owner, with Vassil as the reporting person for those shares.