Toast insider sales: 1.24M shares sold recently; 156k-share sale planned

Rhea-AI Filing Summary

Toast, Inc. (TOST) Form 144: An insider filing notifies the proposed sale of 156,000 Class A shares with an aggregate market value of $6,901,550.45, to be sold on 08/27/2025 through Fidelity Brokerage on the NYSE. The securities are described as option-based (option granted 03/15/2022) and the payment on the proposed sale is cash. The filing also lists prior insider sales by Christopher P. Comparato totaling 1,240,160 shares in the past three months for aggregate gross proceeds of $53,823,735.60.

Positive

• Rule 144 compliance appears complete with broker, dates, quantities, and aggregate market value disclosed
• Transaction details provided (broker name, sale dates, gross proceeds) enabling transparent investor review

Negative

• Large insider selling: 1,240,160 Class A shares sold in the past three months as listed in the filing
• Substantial proceeds: listed gross proceeds for those sales total $53,823,735.60, indicating significant insider liquidity

Insights

Securities Analyst

TL;DR: Significant recent insider sales totaling 1.24M shares; proposed additional sale of 156k shares disclosed under Rule 144.

The filing shows ongoing disposals by an insider, with 1,240,160 Class A shares sold in the prior three months for reported gross proceeds of $53,823,735.60 and a new proposed sale of 156,000 shares valued at $6,901,550.45. This is a routine Rule 144 notice documenting compliance with resale conditions for restricted or control securities and identifies the broker and intended sale date. The disclosure is operationally complete for Rule 144 purposes but does not state the insider's remaining holdings or motivations for the sales.

Corporate Governance Expert

TL;DR: Proper Rule 144 mechanics shown, but large clustered sales warrant investor attention on insider activity.

The form documents that the securities to be sold were tied to an option (granted 03/15/2022) and that sales were executed through a listed broker on the NYSE. From a governance perspective, the filing meets disclosure obligations by listing broker, dates, quantities, and proceeds for recent sales. The pattern of multiple sizable sales within a short period may be material for investors assessing insider confidence, although the filing itself contains no non-public operational information.

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	6901550.45	510000000	08/27/2025	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	08/27/2025	Option Granted - 03/15/2022	Issuer			156000	08/27/2025	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

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 the Form 144 filed for TOST disclose?

The Form 144 discloses a proposed sale of 156,000 Class A shares (aggregate market value $6,901,550.45) planned for 08/27/2025 through Fidelity Brokerage on the NYSE.

Who executed insider sales in the past three months for TOST?

The filing lists Christopher P. Comparato as the seller for multiple transactions totaling 1,240,160 shares across dates in June–August 2025.

How much gross proceeds were reported from recent insider sales?

The listed gross proceeds for the sales shown add up to $53,823,735.60 based on the amounts reported in the filing tables.

What type of acquisition produced the shares to be sold on 08/27/2025?

The securities to be sold are tied to an option granted on 03/15/2022, with the acquisition date for the reported lot shown as 08/27/2025 and payment indicated as cash.

Through which broker will the proposed sale occur?

The proposed sale is to occur through Fidelity Brokerage Services LLC, 900 Salem Street, Smithfield RI and is to be executed on the NYSE.