[Form 4] System1, Inc. Insider Trading Activity

Rhea-AI Filing Summary

System1, Inc. (SST) – Form 4, filed 30-Jul-2025

Chief Financial Officer Tridivesh Kidambi reported two equity transactions dated 28-29 Jul-2025:

• Tax-withholding share surrender: 224 Class A shares automatically withheld on 28-Jul at $7.51 to satisfy taxes on the vesting of 625 previously granted RSUs.
• New equity incentives: (i) grant of 50,000 time-based RSUs at $0 cost; one-third vests 15-Jul-2026 and the balance in eight equal quarterly installments thereafter; (ii) grant of 20,000 Stock Appreciation Rights (SARs) with a $7.09 base price, expiring 29-Jul-2032. SARs vest in 25% tranches as System1 achieves trailing-12-month Adjusted EBITDA milestones of $50 m, $55 m, $60 m and $65 m.

Post-transaction holdings: 121,124 Class A shares (including 56,276 unvested RSUs) and 72,000 SARs, all held directly. Share totals reflect the company’s 1-for-10 reverse split completed 11-Jun-2025.

No open-market purchases or sales by the insider occurred; the filing primarily records equity compensation designed to align the CFO’s incentives with long-term profitability targets.

Positive

• Performance-linked SARs align CFO compensation with EBITDA thresholds, promoting shareholder-aligned incentives.
• No discretionary insider selling; only tax withholding, suggesting neutral-to-positive insider sentiment.

Negative

• None.

Insights

Securities Analyst

TL;DR: Routine incentive grants; no market-moving buy/sell.

The Form 4 shows standard executive compensation rather than discretionary trading. Kidambi surrendered 224 shares for tax, then received 50k RSUs and 20k SARs, boosting potential ownership leverage. The EBITDA-linked SARs encourage profitability, signalling management’s focus on cash earnings. Because no shares were sold for personal gain, the filing does not imply negative insider sentiment. Impact on float and dilution is immaterial: 70k additional rights versus a >100 m post-split share base. Overall, neutral for valuation yet positive for governance alignment.

Corporate Governance Expert

TL;DR: Performance-based SARs strengthen pay-for-performance structure.

The EBITDA hurdle design meets investor preferences for outcome-based awards, and quarterly vesting cadence supports retention. Share surrender for taxes adheres to best-practice withholding. No red flags in timing or magnitude relative to CFO role. Filing is not impactful to shareholders’ economic interests today but underlines efforts to tie compensation to future earnings quality.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
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hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Kidambi Tridivesh

(Last) (First) (Middle)

4235 REDWOOD AVE

(Street)

LOS ANGELES CA 90066

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
System1, Inc. [ SST ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Financial Officer

3. Date of Earliest Transaction (Month/Day/Year)
07/28/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Class A Common Stock	07/28/2025		F		224(1)	D	$7.51	71,124(2)	D
Class A Common Stock	07/29/2025		A		50,000(3)	A	$0	121,124(4)	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Stock Appreciation Rights(5)	$7.09	07/29/2025		A		20,000		(6)	07/29/2032	Class A Common Stock	20,000	$0	72,000(7)	D

Explanation of Responses:

1. 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.

2. Includes 6,276 unvested RSUs.

3. 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.

4. Includes 56,276 unvested RSUs.

5. 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").

6. 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.

7. 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.

Remarks:

	/s/ Daniel Weinrot, Attorney-in-Fact for Tridivesh Kidambi	07/30/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
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FAQ

How many System1 (SST) shares does CFO Tridivesh Kidambi now own?

After the reported transactions, he holds 121,124 Class A shares, including 56,276 unvested RSUs.

What equity awards did System1 grant the CFO on 29-Jul-2025?

He received 50,000 RSUs and 20,000 Stock Appreciation Rights with a $7.09 base price.

When do the newly granted RSUs to the SST CFO vest?

33% vests on 15-Jul-2026; the remaining 67% vests in eight equal quarterly installments thereafter.

What performance goals trigger vesting of the SST SARs?

Each 5,000-SAR tranche vests at trailing-12-month Adjusted EBITDA of $50 m, $55 m, $60 m, and $65 m respectively.

Did the CFO sell any System1 shares in this Form 4?

No. The only share reduction (224 shares) was an automatic tax-withholding action, not an open-market sale.