Toast officer plans $468K Rule 144 stock sale

Rhea-AI Filing Summary

Toast, Inc. (TOST) has a notice of proposed sale of restricted or control securities under Rule 144 filed for Jonathan S. Vassil14,280 shares of Class A common stock, expected around September 2, 2026, in connection with a stock option exercise for cash through Fidelity Brokerage Services LLC on the NYSE. The filing also lists multiple Class A share sales by Jonathan S. Vassil over the prior three months, providing recent trading history as required by Rule 144.

Key Figures

Planned shares to be sold: 14,280 shares of Class A common stock Aggregate market value of planned sale: $468,241.20 Shares outstanding: 514,000,000 shares +3 more

6 metrics

Planned shares to be sold 14,280 shares of Class A common stock Proposed Rule 144 sale associated with stock option exercise around September 2, 2026

Aggregate market value of planned sale $468,241.20 Value listed for 14,280 Class A shares in the securities information section

Shares outstanding 514,000,000 shares Class A shares outstanding for Toast, Inc. as stated in the securities information section

Sale on July 2, 2026 6,647 shares for $191,760.63 Class A shares sold by Jonathan S. Vassil during the past 3 months section

Sale on August 21, 2026 85,280 shares for $3,099,093.92 Largest single Class A sale listed in the past 3 months section

Planned sale date September 2, 2026 Date associated with the proposed 14,280-share sale and stock option exercise

Key Terms

Rule 144, stock option exercise, Class A, attorney-in-fact, +1 more

5 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

stock option exercise financial

"Class A | 09/02/2026 | Stock Option Exercise | Issuer"

A stock option exercise is the act of using a previously granted right to buy shares of a company's stock at a specific, predetermined price by paying that price and receiving the shares. It matters to investors because exercising changes who owns the shares (which can dilute existing ownership), can trigger taxable events and shift potential gains or losses, and affects voting power and the company’s outstanding share count—like turning a voucher into an actual product that becomes part of circulating supply.

Class A financial

"Class A | Fidelity Brokerage Services LLC 900 Salem Street"

Class A denotes a specific group of a company’s shares that carry a particular set of rights—most commonly different voting power or dividend priority compared with other share classes. Think of it like different seats on a bus where some seats let you steer and others only ride: knowing whether a share is Class A tells investors how much influence they have over company decisions and how returns might be distributed, which affects control and value.

attorney-in-fact regulatory

"as attorney-in-fact for Jonathan S. Vassil"

An attorney-in-fact is the person or entity given legal authority through a power of attorney to act on behalf of another for specific tasks, such as signing documents, voting shares, or handling transactions. For investors, this matters because it lets a trusted representative make timely decisions or complete paperwork when the owner cannot, much like handing keys to someone to run errands on your behalf—so checks on scope and limits of that authority are important.

Fidelity Brokerage Services LLC financial

"Class A | Fidelity Brokerage Services LLC 900 Salem Street"

FAQ

What does the Form 144 filing disclose for Toast, Inc. (TOST)?

The Form 144 notice for Toast, Inc. (TOST) discloses a proposed Rule 144 sale by officer Jonathan S. Vassil of 14,280 Class A shares, expected around September 2, 2026, in connection with a stock option exercise for cash through Fidelity Brokerage Services LLC.

How many Toast (TOST) shares are proposed to be sold under this Form 144?

The notice covers a proposed sale of 14,280 shares of Toast, Inc. Class A common stock. The securities to be sold section repeats this amount in connection with a stock option exercise for cash on or about September 2, 2026.

What is the approximate market value of the Toast (TOST) shares covered by this Form 144?

The securities information section lists an aggregate market value of $468,241.20 for the 14,280 Class A shares of Toast, Inc. covered by the proposed Rule 144 sale through Fidelity Brokerage Services LLC.

Who is the selling security holder in this Toast (TOST) Form 144?

The person for whose account the securities are to be sold is Jonathan S. Vassil, identified as an officer of Toast, Inc. The form is signed by Gary Redman as a duly authorized representative of Fidelity Brokerage Services LLC, acting as attorney-in-fact for Vassil.

What prior Toast (TOST) share sales are listed in the past 3 months section?

The filing lists several prior Class A share sales by Jonathan S. Vassil between July 2, 2026 and August 21, 2026, including transactions such as 6,647 shares for $191,760.63 on July 2, 2026 and 85,280 shares for $3,099,093.92 on August 21, 2026.

How many Toast (TOST) shares are outstanding according to this Form 144?

The securities information section states that 514,000,000 shares of Toast, Inc. Class A common stock are outstanding. This figure serves as context for the Rule 144 sale notice.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 09/02/2026 - 11:08 AM Accepted by SEC EDGAR 09/02/2026 - 11:08 AM Learn about SEC filing dates

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0002004790
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	Toast, Inc.
SEC File Number	001-40819
Address of Issuer	333 SUMMER STREET BOSTON MASSACHUSETTS 02210
Phone	617-297-1005
Name of Person for Whose Account the Securities are To Be Sold	Vassil Jonathan
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Officer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Class A	Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI 02917	14280	468241.20	514000000	09/02/2026	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Class A	09/02/2026	Stock Option Exercise	Issuer			14280	09/02/2026	Cash

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
Jonathan S. Vassil 333 Summer Street Boston MA 02210	Class A	07/02/2026	6647	191760.63
Jonathan S. Vassil 333 Summer Street Boston MA 02210	Class A	07/07/2026	3150	94592.61
Jonathan S. Vassil 333 Summer Street Boston MA 02210	Class A	07/13/2026	9170	276867.06
Jonathan S. Vassil 333 Summer Street Boston MA 02210	Class A	07/14/2026	2000	60036.40
Jonathan S. Vassil 333 Summer Street Boston MA 02210	Class A	08/03/2026	14280	469622.08
Jonathan S. Vassil 333 Summer Street Boston MA 02210	Class A	08/05/2026	4700	169308.50
Jonathan S. Vassil 333 Summer Street Boston MA 02210	Class A	08/11/2026	13797	496858.55
Jonathan S. Vassil 333 Summer Street Boston MA 02210	Class A	08/19/2026	13931	501690.43
Jonathan S. Vassil 333 Summer Street Boston MA 02210	Class A	08/21/2026	85280	3099093.92

144: Remarks and Signature

Remarks
Date of Notice	09/02/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	03/13/2026
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	/s/ Gary Redman, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for Jonathan S. Vassil
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)