Toast (TOST) Insider Filing: 154,979 Class A Shares Proposed Sale

Rhea-AI Filing Summary

Toast, Inc. (TOST) filed a Form 144 reporting a proposed sale of 154,979 Class A shares through Fidelity Brokerage Services with an aggregate market value of $6,410,457.25, representing part of 510,000,000 shares outstanding. The shares were acquired via an option (granted 03/10/2023) with an acquisition/sale date listed as 09/04/2025 and payment noted as cash. The filing also lists 13 prior sales by Christopher P. Comparato between 06/20/2025 and 09/03/2025, including a largest single sale of 175,000 shares on 08/07/2025 for $7,943,495.00. The filer certifies no undisclosed material adverse information and includes the required signature attestation.

Positive

• Filing provides full Rule 144 disclosure including broker, share counts, acquisition method, and aggregate market value
• Transaction executed through a major broker (Fidelity), indicating standard settlement procedures
• Payment method is cash and acquisition origin is documented (option granted 03/10/2023)

Negative

• Frequent insider sales: 13 sales by Christopher P. Comparato from 06/20/2025 to 09/03/2025 may be viewed negatively by some investors
• Insider selling of a material dollar amount (proposed $6.41M sale plus prior multi-million-dollar sales) could be perceived as reduced insider ownership

Insights

Securities Analyst

TL;DR: Insider plans a one-time sale of 154,979 shares while multiple recent disposals by the same individual suggest ongoing liquidity events.

The filing documents a proposed sale executed through a broker with clear acquisition details: option grant date 03/10/2023 and acquisition/sale date 09/04/2025. The aggregate value of the proposed sale is $6.41 million against 510 million shares outstanding, which is immaterial to outstanding share count but notable at the individual level. The record of 13 prior sales from June through early September 2025 demonstrates sustained insider selling activity. From a market-impact perspective, the single proposed block is unlikely to move the stock materially given the company’s public float, but cumulative insider sales could warrant monitoring.

Corporate Governance Expert

TL;DR: Filing complies with Rule 144 disclosure requirements; repeated insider sales raise governance questions about insider liquidity timing.

The Form 144 supplies required details: broker identity, number of shares, aggregate market value, and the nature of acquisition (option). The signer affirms no undisclosed material adverse facts. While compliance appears complete, the series of recent sales by Christopher P. Comparato between 06/20/2025 and 09/03/2025 indicates ongoing monetization of holdings. This pattern is governance-relevant for investors assessing insider alignment but does not in itself indicate a disclosure failure or regulatory issue.

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	154979	6410457.25	510000000	09/04/2025	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	09/04/2025	Option Granted - 03/10/2023	Issuer			154979	09/04/2025	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
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	09/02/2025	156000	6834094.80
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	09/03/2025	156000	6582598.37

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 did Toast (TOST) report on this Form 144?

TOST reported a proposed sale of 154,979 Class A shares through Fidelity with an aggregate market value of $6,410,457.25.

Who is the seller named in the filing?

The filing lists Christopher P. Comparato as the seller for prior sales; the proposed sale specifies the person for whose account the securities are to be sold.

When were the shares acquired that are being sold under this Form 144?

Acquisition date is listed as 09/04/2025 with the securities originating from an option granted on 03/10/2023.

How many prior insider sales does the filing show?

13 prior sales by Christopher P. Comparato are listed between 06/20/2025 and 09/03/2025, including a largest single sale of 175,000 shares on 08/07/2025 for $7,943,495.00.

Through which broker will the proposed sale be executed?

Fidelity Brokerage Services LLC (900 Salem Street, Smithfield, RI) is named as the broker.