SST Insider Filing: COO Receives Major RSU Award Post-Reverse Split

Rhea-AI Filing Summary

System1, Inc. (SST) – Form 4 insider filing: President, COO and Director Charles Ursini reported the grant of 337,500 Class A RSUs on 29-Jul-2025. The award was made at $0 cost as part of his ongoing employment agreement.

The RSUs vest one-third on 15-Jul-2026; the remaining two-thirds vest in eight equal quarterly tranches thereafter, subject to continued employment. Following the grant, Ursini’s total beneficial ownership is 367,500 shares, which includes the newly issued unvested RSUs.

The filing also notes that the share count reflects System1’s 1-for-10 reverse split completed on 11-Jun-2025. No shares were sold or disposed; the transaction increases insider alignment but adds potential future dilution once the RSUs settle.

Positive

• Enhanced insider alignment: COO now holds 367,500 shares, reinforcing management’s equity stake.
• Retention signal: Multi-year vesting schedule incentivizes leadership continuity after recent corporate actions.

Negative

• Future dilution risk: Settlement of 337,500 RSUs will increase share count over the next three years.

Insights

Equity Compensation Analyst

TL;DR: Large RSU grant aligns COO post-reverse split; neutral impact unless share count is material.

The 337,500-share RSU package, post 1-for-10 reverse split, equals 3.375 M pre-split shares—sizeable but typical for C-suite retention. Because it vests over 3+ years, immediate dilution is limited and expense will be recognized gradually under ASC 718. No open-market buying occurred, so signaling value is modest. The award does boost insider exposure and may reassure investors on leadership stability after the June split. Overall capital impact depends on SST’s fully diluted share base, which the filing does not disclose.

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

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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^*

Ursini Charles

(Last) (First) (Middle)

4235 REDWOOD AVENUE

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President & COO

3. Date of Earliest Transaction (Month/Day/Year)
07/29/2025

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	07/29/2025		A		337,500(1)	A	$0	367,500(2)(3)	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. The Reporting Person was granted 337,500 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. Ursini 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.

2. Includes 337,500 unvested RSUs.

3. Represents the total number of shares held 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 Charles Ursini	07/31/2025
	** 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 did Charles Ursini acquire?

He received 337,500 restricted stock units, each convertible into one Class A share upon vesting.

What is the vesting schedule for the new RSUs?

One-third vests on 15-Jul-2026; the remaining two-thirds vest in eight equal quarterly installments thereafter.

Did the insider buy or sell shares on the open market?

No. The transaction code "A" denotes an award; no shares were purchased or sold for cash.

What is Charles Ursini’s total beneficial ownership after the grant?

He now beneficially owns 367,500 Class A shares, including the unvested RSUs.

How does System1's recent reverse split affect the share numbers?

All figures reflect the 1-for-10 reverse stock split completed on 11-Jun-2025.