[Form 4] System1, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Form 4 shows insider activity at System1, Inc. (SST). General Counsel & Secretary Daniel J. Weinrot had two reportable events:

• 28 Jul 2025 – Tax-withholding disposition: 191 Class A shares were automatically withheld at $7.51 per share (≈ $1.4 k) to cover taxes on the vesting of 375 previously granted RSUs.
• 29 Jul 2025 – New equity grant: Weinrot received 52,500 RSUs for continued employment. Vesting schedule: one-third on 15 Jul 2026; remaining two-thirds in eight equal quarterly tranches thereafter. Each RSU converts to one Class A share at no cost.

Post-transaction ownership: 70,578 Class A shares, including 57,270 unvested RSUs. No derivative securities were involved.

Positive

• 52,500-share RSU grant strengthens management ownership incentives over a three-year horizon.
• No discretionary open-market selling; only 191 shares disposed for tax withholding, signaling confidence.

Negative

• Incremental share dilution from new RSUs, though small, adds to overhang.
• Vesting is purely time-based; no performance conditions were disclosed, limiting pay-for-performance linkage.

Insights

Equity Research Analyst

TL;DR: Large RSU award deepens insider stake; only minimal shares sold for taxes—signal is modestly constructive but not materially price-moving.

The 52.5 k RSU grant increases Weinrot’s potential equity by ~0.05 % of SST’s 108 m basic shares, a negligible dilution impact. Because the grant vests over three years, it acts as a retention device and better aligns management incentives with shareholders. The 191-share tax sale is routine and immaterial (<$2 k). No open-market selling occurred, so the filing offers slightly positive governance optics but lacks fundamental information to alter earnings or valuation models. I rate the impact neutral-to-slightly positive.

Corporate Governance Specialist

TL;DR: Time-based RSU grant supports retention; staggered vesting ensures alignment but adds incremental dilution; governance posture acceptable.

The multi-year vesting schedule ties Weinrot’s compensation to share-price performance, which is good practice. Incremental dilution is de minimis and within typical mid-cap norms. Absence of derivative transactions simplifies the structure and reduces complexity risk. Overall, the filing suggests standard incentive alignment with no red flags.

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
Estimated average burden
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^*

Sestanovich Elizabeth

(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 People 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		135(1)	D	$7.51	20,317(2)	D
Class A Common Stock	07/29/2025		A		40,000(3)	A	$0	60,317(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

Explanation of Responses:

1. Upon the vesting of 375 restricted stock units ("RSUs") previously granted to the reporting person, the Company withheld 135 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.

2. Includes 4,770 unvested RSUs.

3. The Reporting Person was granted 40,000 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 Ms. Sestanovich 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 44,770 unvested RSUs.

Remarks:

	/s/ Daniel Weinrot, Attorney-in-Fact for Elizabeth Sestanovich	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.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

How many System1 (SST) shares does Daniel Weinrot now own?

He reports 70,578 Class A shares, of which 57,270 are unvested RSUs.

What was the size of the new RSU grant to SST's General Counsel?

Weinrot received 52,500 restricted stock units on 29 Jul 2025 at no cost.

When will the newly granted RSUs vest?

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

Did the insider sell any SST shares on the open market?

No. Only 191 shares were surrendered to cover tax withholding—there was no open-market sale.

Is there any derivative security activity reported?

No derivative securities (options, warrants, etc.) were acquired or disposed of in this filing.