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) filed a Form 4 reporting an automatic share withholding tied to equity compensation. On 10/15/2025, Chief Ad Operations Officer Brian Coppola had 377 shares of Class A common stock withheld at $7.94 per share (code F) to cover taxes upon the vesting of 754 RSUs.
Following the transaction, Coppola beneficially owned 67,066 shares in total, which includes 44,708 unvested RSUs. The filing reflects a non‑open market, tax‑withholding event rather than a discretionary purchase or sale.
System1, Inc. (SST) reported insider activity by its Chief Financial Officer, Tridivesh Kidambi. A Form 4 shows an F-coded transaction on 10/15/2025 where 352 shares of Class A common stock were withheld at $7.94 per share to satisfy tax obligations tied to the vesting of 837 RSUs.
Following this event, the reporting person beneficially owns 120,772 shares. This figure includes 55,439 unvested RSUs as noted in the footnotes.
System1, Inc. (SST) reported an insider transaction by Chief People Officer Elizabeth Sestanovich. On 10/15/2025, 282 shares of Class A Common Stock were withheld at $7.94 per share to satisfy tax obligations upon the vesting of 670 RSUs, coded “F” (tax withholding).
Following the transaction, she beneficially owned 60,035 shares directly. This figure includes 44,100 unvested RSUs, as noted in the footnotes.
System1, Inc. (SST) reported an insider equity transaction by its General Counsel & Secretary, Daniel J. Weinrot. On 10/15/2025, 670 restricted stock units vested, and the company withheld 382 shares at
Following the transaction, the reporting person beneficially owned 70,196 shares. This figure includes 56,600 unvested RSUs, reflecting both vested holdings and remaining unvested awards.
CEE Holdings Trust, a reporting person identified as a director of System1, Inc. (SST), purchased 11,015 shares of Class A common stock on 08/22/2025 at a weighted-average price of $7.32 per share. After the transaction the trust beneficially owned 919,555 shares. The filing states the purchase occurred in multiple trades at prices ranging from $6.79 to $7.50, and the trustee who signed the Form 4 is Brittany Gale of Jackson Hole Trust Company. This disclosure reports an insider acquisition by a director and provides the mandatory details required under Section 16.
System1, Inc. (SST) director CEE Holdings Trust, via Jackson Hole Trust Company, reported three open-market purchases of Class A common stock on 08/19/2025, 08/20/2025 and 08/21/2025. The filings show 6,567 shares purchased at a weighted average $6.32 on 08/19/2025, 12,584 shares at $6.25 on 08/20/2025, and 12,584 shares at $6.90 on 08/21/2025. After these transactions the reporting person beneficially owned 908,540 Class A shares, reflecting post-transaction totals that account for a 1-for-10 reverse stock split completed June 11, 2025. Footnotes note the reported prices are weighted averages across multiple trades.
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