Tridivesh Kidambi - 28 Jul 2025 Form 4 Insider Report for System1, Inc. (SST)

Signature
/s/ Daniel Weinrot, Attorney-in-Fact for Tridivesh Kidambi
Issuer symbol
SST
Transactions as of
28 Jul 2025
Net transactions value
-$1,682
Form type
4
Filing time
30 Jul 2025, 19:41:34 UTC
Previous filing
17 Jul 2025
Next filing
17 Oct 2025

Reporting Owners (1)

Name Relationship Address Signature Signature date CIK
Kidambi Tridivesh Chief Financial Officer 4235 REDWOOD AVE, LOS ANGELES /s/ Daniel Weinrot, Attorney-in-Fact for Tridivesh Kidambi 30 Jul 2025 0001906862

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction SST Class A Common Stock Tax liability $1,682 -224 -0.31% $7.51 71,124 28 Jul 2025 Direct F1, F2
transaction SST Class A Common Stock Award $0 +50,000 +70% $0.000000 121,124 29 Jul 2025 Direct F3, F4

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
transaction SST Stock Appreciation Rights Award $0 +20,000 +38% $0.000000 72,000 29 Jul 2025 Class A Common Stock 20,000 $7.09 Direct F5, F6, F7
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 Upon the vesting of 625 restricted stock units ("RSUs") previously granted to the reporting person, the Company withheld 224 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.
F2 Includes 6,276 unvested RSUs.
F3 The Reporting Person was granted 50,000 restricted stock units ("RSUs") in connection with his continued employment with System1, Inc. ("SST"). Each RSU represents the right to receive one share of SST Class A Common Stock upon vesting. Subject to the continued employment of Mr. Kidambi through the applicable vesting date, one-third of the RSUs will vest on July 15, 2026, and the remaining two-thirds will vest in 8 substantially equal quarterly installments on each quarterly anniversary thereafter.
F4 Includes 56,276 unvested RSUs.
F5 These stock appreciation rights (the "SARs") were granted to the Reporting Person pursuant to the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and a corresponding Stock Appreciation Rights Grant Notice and Award Agreement between System1, Inc. (the "Issuer") and the Reporting Person. The SARs reported on this Form 4 represent the right to receive (at the Issuer's discretion), upon exercise of the SARs by the Reporting Person, a payment in either (x) Class A Common Stock, par value $0.0001 per share ("Class A Common Stock") or (y) cash, in the amount equal to the number of shares of Class A Common Stock underlying the number of SARs being exercised multiplied by the excess of the fair market value of one share of Class A Common Stock on (i) the date the SARs are exercised, and (ii) $7.09, the Issuer's closing price on July 29, 2025 (the date the SARs were granted, the "Grant Date").
F6 These Stock Appreciation Rights (the "SARs") were granted to the Reporting Person on July 29, 2025 under the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and vest (i) 25% (or 5,000 SARs) upon the Issuer first achieving trailing twelve month Adjusted EBITDA ("TTM Adjusted EBITDA") of $50.0 million after the date of grant, (ii) 25% (or 5,000 SARs) upon the Issuer first achieving TTM Adjusted EBITDA of $55.0 million after the date of grant, (iii) 25% (or 5,000 SARs) upon the Issuer first achieving TTM Adjusted EBITDA of $60.0 million after the date of grant and (iv) 25% (or 5,000 SARs) upon the Issuer first achieving TTM Adjusted EBITDA of $65.0 million after the date of grant, in each case, subject to the terms of the Plan and an award agreement entered into between the Reporting Person and the Issuer pursuant to the Plan.
F7 Represents the total number of SARs held by the Reporting Person after the Issuer's completion of a 1-for-10 reverse stock split that occurred on June 11, 2025.