Toast CRO exercises options, sells 13,931 shares
Toast, Inc. (TOST) reported that Chief Revenue Officer Jonathan Vassil exercised stock options and sold shares on August 19, 2026 under a Rule 10b5-1 trading plan adopted on March 13, 2026.
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Form Type
4
Rhea-AI Filing Summary
Toast, Inc. (TOST) reported that Chief Revenue Officer Jonathan Vassil exercised stock options and sold shares on August 19, 2026 under a Rule 10b5-1 trading plan adopted on March 13, 2026. He exercised options for 7,399 and 6,532 shares of Class A common stock at exercise prices of $17.38 and $17.33 per share, respectively, receiving the same number of Class A shares. He then sold a total of 13,931 Class A shares at a weighted average price of $36.013 per share, with individual sale prices ranging from $36 to $36.09. Following these transactions, 84,269 Class A shares are reported as held indirectly through The Jonathan S. Vassil Grantor Retained Annuity Trust #1.
Insider Trade Summary 10b5-1
Exercise and Sale: 13,931 shares ($260K approx. pre-tax spread)
Exercise and Sale
6 txns
Insider
Vassil Jonathan
Role
Chief Revenue Officer
Sold
13,931 shs ($502K)
Approx. gross sale proceeds
$502K
Approx. exercise cost
$242K
Approx. pre-tax spread
$260K
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Option (Right to Buy) F1, F3 | 7,399 | $0.00 | $0.00 |
| Exercise | Stock Option (Right to Buy) F1, F4 | 6,532 | $0.00 | $0.00 |
| Exercise | Class A Common Stock F1 | 7,399 | $17.38 | $129K |
| Exercise | Class A Common Stock F1 | 6,532 | $17.33 | $113K |
| Sale | Class A Common Stock F1, F2 | 13,931 | $36.013 | $502K |
| holding | Class A Common Stock | -- | -- | -- |
Holdings After Transaction:
Stock Option (Right to Buy) — 451,111 contracts (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 $36.09 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
Options exercised (first grant): 7,399 shares
Exercise price (first grant): $17.38 per share
Options exercised (second grant): 6,532 shares
+5 more
8 metrics
Options exercised (first grant)
7,399 shares
Stock options exercised into Class A Common Stock at $17.38 per share on August 19, 2026
Exercise price (first grant)
$17.38 per share
Exercise price for 7,399 stock options converted to Class A Common Stock
Options exercised (second grant)
6,532 shares
Stock options exercised into Class A Common Stock at $17.33 per share on August 19, 2026
Exercise price (second grant)
$17.33 per share
Exercise price for 6,532 stock options converted to Class A Common Stock
Shares sold
13,931 shares
Class A Common Stock sold on August 19, 2026
Weighted average sale price
$36.013 per share
Weighted average price for 13,931 Class A shares sold, with a range of $36–$36.09
Indirect holdings after transactions
84,269 shares
Class A Common Stock held indirectly via The Jonathan S. Vassil Grantor Retained Annuity Trust #1
Option expiration dates
March 15, 2032 and March 10, 2033
Expiration dates for the option grants that were exercised on August 19, 2026
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 adopted"
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)"
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What did Toast, Inc. (TOST) executive Jonathan Vassil report in this Form 4?
He reported exercising stock options for 13,931 shares of Toast, Inc. Class A common stock and selling 13,931 shares on August 19, 2026, with remaining indirect holdings of 84,269 shares held through a Grantor Retained Annuity Trust.
How many Toast, Inc. (TOST) options did Jonathan Vassil exercise and at what prices?
He exercised options on 7,399 shares at an exercise price of $17.38 per share and 6,532 shares at an exercise price of $17.33 per share, receiving the same number of Toast, Inc. Class A common shares in each case.
Were Jonathan Vassil’s Toast, Inc. (TOST) transactions under a Rule 10b5-1 plan?
Yes. The filing states that the transactions were effected pursuant to a Rule 10b5-1 trading plan adopted by Jonathan Vassil on March 13, 2026, and the form’s Rule 10b5-1 checkbox is marked as affirmed.
What is the nature of Jonathan Vassil’s indirect Toast, Inc. (TOST) holdings?
The Form 4 reports 84,269 Toast, Inc. Class A shares held indirectly through The Jonathan S. Vassil Grantor Retained Annuity Trust #1, a grantor retained annuity trust associated with the reporting person.
AI-generated analysis. How Rhea-AI works. Not financial advice.
