[144] Toast, Inc. SEC Filing

Rhea-AI Filing Summary

Toast insider Christopher P. Comparato filed a Form 144 reporting proposed and completed sales of Class A common stock. The notice lists a proposed sale of 156,000 Class A shares through Fidelity Brokerage Services with an aggregate market value of $7,453,680 and an approximate sale date of 09/03/2025 on the NYSE. The filing also itemizes acquisitions by option exercise on 09/03/2025 totaling 156,000 shares (37,090 and 118,910) with cash payment, and records multiple completed sales by Mr. Comparato between 06/20/2025 and 09/02/2025 totaling several transactions and proceeds shown per trade.

The filer certifies no material nonpublic information is known and provides broker and transaction details as required by Rule 144.

Positive

• Comprehensive disclosure of broker, share counts, aggregate market value, and sale dates consistent with Rule 144 requirements
• Attestation provided that the filer does not know material nonpublic information, meeting compliance expectations

Negative

• Significant insider selling activity recorded across multiple transactions from 06/20/2025 to 09/02/2025, which may be viewed unfavorably by some investors
• Proposed sale of 156,000 shares with material aggregate market value could dilute perceived insider confidence

Insights

Securities Analyst

TL;DR Insider Christopher Comparato reported sizable, serial Class A sales and a proposed sale, showing ongoing monetization of holdings.

The filing documents a proposed sale of 156,000 Class A shares via Fidelity with an aggregate market value of $7,453,680 and multiple completed sales from June through early September 2025 with gross proceeds listed per transaction. It also shows option exercises dated 09/03/2025 that generated 156,000 shares paid in cash. For investors, the filing is a clear, rule-compliant disclosure of liquidity events by a named insider rather than an operational update by the issuer.

Corporate Governance Expert

TL;DR The Form 144 provides transparent disclosure of insider transactions and includes the required attestation regarding material nonpublic information.

The report includes broker identification, share counts, aggregate market value for the proposed sale, acquisition details (option grants and cash payment), and a sequence of completed sales with gross proceeds. The attestation that the filer is unaware of undisclosed material adverse information aligns with Rule 144 compliance expectations. This is procedural disclosure rather than a governance event.

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	7453680.00	510000000	09/03/2025	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	09/03/2025	Option Granted - 03/15/2022	Issuer			37090	09/03/2025	Cash
Class A	09/03/2025	Option Granted - 03/10/2023	Issuer			118910	09/03/2025	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

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 insider sales did Toast (TOST) report on this Form 144?

The filing lists multiple completed sales by Christopher P. Comparato between 06/20/2025 and 09/02/2025 and a proposed sale of 156,000 Class A shares with an aggregate market value of $7,453,680 slated for 09/03/2025.

Who is the filer and how many shares has the filer proposed to sell?

The filer is Christopher P. Comparato and the proposed sale is 156,000 Class A shares via Fidelity Brokerage Services.

Were the shares to be sold acquired by purchase or other means?

The filing shows the shares were acquired by option exercises dated 03/15/2022 and 03/10/2023, with the exercises recorded as acquired on 09/03/2025 and paid in cash.

What broker is handling the proposed sale and on which exchange?

The proposed sale lists Fidelity Brokerage Services LLC and names the NYSE as the securities exchange.

Does the filer certify possession of material nonpublic information?

Yes; by signing the notice the filer represents that he does not know any material adverse information about the issuer that has not been publicly disclosed.