TOST insider filing: Proposed 156,000-share sale and recent insider trades

Rhea-AI Filing Summary

Toast, Inc. (TOST) Form 144 shows a proposed sale of 156,000 Class A shares through Fidelity Brokerage Services with an aggregate market value of $6,800,820, scheduled approximately for 09/02/2025 on the NYSE. The filing states the shares were acquired under an option granted 03/15/2022 and the listed acquisition/payment dates are 09/02/2025 with payment in cash.

The filing also discloses multiple recent open-market sales by Christopher P. Comparato during June–August 2025, with individual sale amounts and gross proceeds reported for each date. The notice includes the required attestation that the seller has no undisclosed material adverse information.

Positive

• Planned sale is properly disclosed under Rule 144 with broker, share count, market value, and acquisition details provided
• Acquisition source is stated (option granted 03/15/2022), which clarifies the basis for the shares being sold

Negative

• Significant insider selling is reported (156,000 shares planned plus multiple sales by the same insider in June–August 2025), which may increase share supply
• No 10b5-1 plan adoption date disclosed in this filing, so the timing rationale for the planned sale is not documented here

Insights

Financial Analyst

TL;DR: Material insider sales are reported but this filing documents a routine Rule 144 disposition rather than new operational news.

The Form 144 indicates a planned disposition of 156,000 Class A shares valued at $6.8 million, with acquisition via an option granted in 2022 and cash payment on sale. Multiple prior sales by the same individual are listed across June–August 2025, showing ongoing liquidity events by an insider. For investors, these are notable for share supply and insider behavior but the filing contains no company financial results or operational changes.

Compliance / Governance Specialist

TL;DR: The filing appears to satisfy Rule 144 disclosure requirements and records recent insider sales; no compliance exceptions are evident in the form content.

The document provides the broker, planned sale date, class, share count, market value, and acquisition details including option grant date. It includes the seller's representation about absence of undisclosed material adverse information. There is no indication in this filing of a trading plan adoption date or other 10b5-1 specifics, and no statements of exceptions or gifts. The filing therefore functions as a regulatory notice of proposed sale.

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

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

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

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	156000	6800820.00	510000000	09/02/2025	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	09/02/2025	Option Granted - 03/15/2022	Issuer			156000	09/02/2025	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
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	06/20/2025	70000	2966558.00
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	07/17/2025	70000	3224676.00
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/07/2025	175000	7943495.00
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/11/2025	124509	5418867.27
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/13/2025	124509	5406305.29
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/14/2025	124509	5339755.23
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/18/2025	124509	5292018.48
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/20/2025	124509	5236362.95
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/21/2025	152615	6436568.15
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/25/2025	150000	6559129.23
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/27/2025	156000	6901549.20
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	08/28/2025	156000	7008362.40

144: Remarks and Signature

Remarks

Date of Notice

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

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What does Toast (TOST) Form 144 disclose about the proposed sale?

The filing discloses a proposed sale of 156,000 Class A shares via Fidelity on approximately 09/02/2025 with aggregate market value $6,800,820.

Who is the seller listed in the Form 144 for TOST?

The selling individual associated with recent sales is Christopher P. Comparato, whose address and multiple sale dates are listed in the filing.

How were the shares being sold acquired according to the filing?

The shares were acquired under an option granted on 03/15/2022, with the acquisition date listed as 09/02/2025 and payment in cash.

Does the filing show prior sales by the same person?

Yes. The filing lists multiple sales by Christopher P. Comparato between 06/20/2025 and 08/28/2025, with amounts and gross proceeds reported for each date.

On which exchange is the planned sale to occur?

The planned sale is listed to occur on the NYSE.