Welcome to our dedicated page for System1 SEC filings (Ticker: SST), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
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System1, Inc. (SST) – Form 4 filed 4 Aug 2025
Director Caroline Horn reported the award of 15,000 restricted stock units (RSUs) on 31 Jul 2025 under the 2022 Incentive Award Plan. The RSUs convert into Class A common stock on a 1-for-1 basis and vest in four equal quarterly installments on 15 Sep 2025, 15 Dec 2025, 15 Mar 2026 and 15 Jun 2026, contingent on her continued board service. No cash was paid (grant price $0).
Following the grant, Horn’s beneficial ownership rose to 37,418 Class A shares, which includes the 15,000 unvested RSUs. The share count reflects System1’s 1-for-10 reverse stock split completed 11 Jun 2025.
The filing signals director retention and modestly strengthens insider alignment, but the incremental issuance is immaterial relative to System1’s total outstanding shares and has no immediate earnings impact.
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.
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.
System1, Inc. (SST) Chief Ad Operations Officer Brian Coppola reported two insider equity transactions on Form 4. On 07/28/25, 206 Class A shares were withheld (Code F) at $7.51 to cover taxes on the vesting of 469 previously-awarded RSUs, reducing his directly-held stock to 27,443 shares. The next day, 07/29/25, Coppola received a grant of 40,000 new RSUs (Code A) at no cost. One-third of the grant will vest on 15 Jul 2026, with the remaining two-thirds vesting in eight equal quarterly installments thereafter, contingent on continued employment. After the grant, his reported beneficial ownership increased to 67,443 shares, including 45,462 unvested RSUs. No derivative securities were exercised or sold, and there was no open-market buying or selling. The filing reflects routine equity compensation and tax-withholding activity rather than a directional view on System1’s share value.
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