TOST Form 144: Comparato plans fourth 70k-share sale in four months

Rhea-AI Filing Summary

Toast, Inc. (symbol: TOST) has filed a Form 144 notice indicating a further insider share sale. Christopher P. Comparato has notified the SEC of his intention to dispose of 70,000 Class A shares on or about 20 June 2025 through Fidelity Brokerage Services on the NYSE. The shares carry an aggregate market value of $2,966,557.10, implying a per-share reference price of roughly $42.38. Compared with the issuer’s 498 million shares outstanding, the planned trade represents approximately 0.014 % of the float.

The filing also discloses that Comparato has already sold 210,000 Class A shares during the past three months—

• 20 Mar 2025: 70,000 shares for $2,499,462
• 17 Apr 2025: 70,000 shares for $2,394,651
• 14 May 2025: 70,000 shares for $3,132,066

—generating combined gross proceeds of approximately $8.0 million. Including the proposed sale, Comparato will have disposed of 280,000 shares over a four-month period.

The securities to be sold were acquired via an option granted on 8 Feb 2019 and exercised on 20 Jun 2025, with the purchase price paid in cash. No other relationships or material terms are provided, and the filer affirms that he is not in possession of undisclosed adverse information about Toast.

Key take-aways for investors:

• Continued insider selling trend may signal profit-taking or diversification.
• Transaction size is modest relative to Toast’s market capitalization but sizeable in absolute dollar terms.
• Form 144 is a notice of intent; the sale may or may not ultimately occur in full.

Insights

Financial Analyst

TL;DR: Insider plans another $3 m stock sale, extending a $8 m three-month trend—modestly negative sentiment.

The filing shows Christopher P. Comparato intends to sell an additional 70 k shares (~$3 m). Although only 0.014 % of shares outstanding, it follows three consecutive monthly disposals totalling 210 k shares. Persistent insider selling can dampen investor sentiment, especially ahead of potential catalysts, even when volumes are small relative to float. The transaction arises from option exercises, so some level of profit realisation is expected, yet the pattern signals limited short-term alignment with share appreciation. Because Form 144 is merely a notice, execution risk remains, but markets often price in the intent. Overall impact: modestly negative.

Corporate Governance Specialist

TL;DR: Repeated sales raise governance optics but size versus float limits material impact.

Rule 144 filings provide transparency into insider activity. Comparato’s four-month sequence of 70 k-share sales suggests a pre-arranged disposition cadence, possibly linked to a 10b5-1 plan, though the form leaves that box blank. From a governance angle, steady liquidation by a key individual can create perception issues, yet disclosure mitigates regulatory risk. The absence of adverse-information acknowledgment is standard. Investors should monitor whether additional sales breach the 1 % or volume limits set by Rule 144; current cumulative 280 k shares remain well below those thresholds. I classify the market effect as mildly negative but not fundamentally disruptive.

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	70000	2966557.10	498000000	06/20/2025	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	06/20/2025	Option Granted - 02/08/2019	Issuer			70000	06/20/2025	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	03/20/2025	70000	2499462.00
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	04/17/2025	70000	2394651.00
Christopher P. Comparato 333 Summer Street Boston MA 02210	Class A	05/14/2025	70000	3132066.00

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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

How many Toast (TOST) shares are being proposed for sale in the latest Form 144?

The filing covers 70,000 Class A shares with an aggregate market value of $2,966,557.10.

What is the estimated date of the Toast insider sale?

The approximate sale date listed is 20 June 2025.

How much stock has the filer sold in the past three months?

Christopher P. Comparato sold 210,000 shares between March and May 2025 for about $8.0 million in proceeds.

What percentage of Toast’s outstanding shares does the proposed 70,000-share sale represent?

With 498 million shares outstanding, the proposed sale equals roughly 0.014 % of total shares.

Does the Form 144 guarantee that the Toast shares will be sold?

No. Form 144 is a notice of intent; the shares may or may not ultimately be sold.