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System1, Inc. reported that Chief People Officer Elizabeth Sestanovich had 7,058 shares of Class A common stock withheld on July 15, 2026 to satisfy tax obligations on the vesting of 13,870 restricted stock units (RSUs). After this tax-withholding disposition, she directly held 51,890 shares, including 28,140 unvested RSUs.
System1, Inc. executive Brian Coppola, Chief Ad Operations Officer, reported a tax-withholding disposition of 6,124 shares of Class A Common Stock at $2.60 per share. The shares were withheld upon the vesting of 13,954 RSUs. After this event, he holds 59,774 shares directly, including 28,308 unvested RSUs.
System1, Inc. Chief Financial Officer Kidambi Tridivesh reported a tax-withholding disposition of 6,022 shares of Class A Common Stock on July 15, 2026, at $2.60 per share. The company withheld these shares to cover taxes on the vesting of 17,338 RSUs. After this event, Tridivesh directly holds 175,793 shares, including 35,176 unvested RSUs.
System1, Inc. reported an insider equity event for General Counsel & Secretary Daniel J. Weinrot. Upon vesting of 17,995 restricted stock units (RSUs), the company withheld 9,156 shares of Class A Common Stock at $2.60 per share to satisfy his tax withholding obligation.
After this non-market tax-withholding disposition, Weinrot directly holds 59,897 shares of Class A Common Stock, which includes 36,515 unvested RSUs. No open-market purchase or sale of shares occurred as part of this transaction.
System1, Inc. is asking stockholders to approve issuing 39,250 shares of Series A Cumulative Convertible Preferred Stock as part of a comprehensive debt exchange with its lenders. These preferred shares, with an initial stated value of $39.25 million, are initially convertible at $10.40 into 3,775,000 shares of Class A common stock, representing about 37.8% of common stock outstanding as of June 18, 2026. The transaction would replace existing loans with a new $150.0 million term loan, the preferred shares and cash consideration of $31,379,300.18, while settling ongoing litigation and extending debt maturity to January 14, 2031. Preferred holders would receive a 7.0% cumulative dividend, priority on liquidation, the right to elect one director while at least 19,625 preferred shares are outstanding, and consent rights over certain financings and corporate actions while at least 9,812 shares remain outstanding. Stockholders are also being asked to elect three Class I directors and ratify Deloitte & Touche LLP as auditor for the year ending December 31, 2026.
Kidambi Tridivesh reported acquisition or exercise transactions in this Form 4 filing.
System1, Inc. reported that Chief Financial Officer Tridivesh Kidambi received a grant of 35,300 restricted stock units, each equal to one share of Class A Common Stock. The award was fully vested on the grant date, increasing his direct holdings to 181,815 shares. This total includes 52,514 unvested RSUs that remain subject to vesting conditions.
System1, Inc. entered into a comprehensive exchange agreement with all existing term loan and revolver lenders to overhaul its capital structure and settle all outstanding disputes. The company will replace its $252.6 million term loan and $50.0 million revolver with a new $150.0 million term loan maturing in January 2031, the issuance of 39,250 shares of Series A Cumulative Convertible Preferred Stock with an aggregate initial stated value of $39.3 million, and a one-time cash payment of about $31.4 million.
The preferred stock carries a 7.00% annual cumulative dividend, a liquidation preference at 1.0x stated value plus accrued dividends, and is initially convertible at $10.40 per share, representing roughly 27.4% of common equity on an as-converted basis. Holders gain the right to elect one independent director and receive consent rights over certain actions, including additional indebtedness above $175.0 million. The new term loan bears interest at SOFR + 5.00%, with up to 50% payable in kind and quarterly amortization of $375,000.
The company states that, at closing, total indebtedness will have been reduced by over $160 million from the beginning of the year and maturities extended to 2031, with 100% lender participation. Closing is subject to stockholder approval of the preferred share issuance and other conditions, and is expected in the third quarter of 2026.
System1, Inc. reported first quarter 2026 results with revenue of $37.2 million, down from $74.5 million a year earlier. GAAP gross profit was $23.3 million with a 63% margin, and adjusted gross profit was $28.2 million with a 76% margin.
The company recorded a GAAP net loss of $57.6 million, compared with a $19.9 million net loss in the prior-year quarter, largely reflecting a $36.8 million impairment of long-lived assets. Adjusted EBITDA was $2.7 million, down from $12.1 million, as management emphasized cost actions and capital structure changes aimed at improving the financial profile.
System1, Inc. files Amendment No. 1 to its 2025 annual report to add governance, compensation and ownership details that were originally expected in a later proxy statement.
The filing outlines a seven‑member board, with CEO Michael Blend also serving as chairman and five directors deemed independent under NYSE rules. It describes the audit, compensation, and nominating committees and their chairs, as well as meeting frequency and director attendance.
Executive pay data show 2025 total compensation of $3.47 million for President & COO Charles Ursini, $1.45 million for CFO Tridivesh Kidambi and $9.55 million for CouponFollow President Marc Mezzacca, largely driven by stock appreciation rights and CouponFollow earnout payments. The company reports a 2025 GAAP net loss of $81.2 million and details how “compensation actually paid” to named executives tracks changes in equity values. The amendment also discloses director retainers and RSU grants, major shareholders’ stakes, remaining shares available under equity plans and Deloitte audit fees of $1.73 million for 2025.
System1, Inc. Chief Financial Officer Kidambi Tridivesh purchased 26,910 shares of Class A Common Stock at $3.00 per share. The shares were bought in a privately negotiated, arm’s length transaction from another existing holder, rather than through the stock exchange.
Separately, upon vesting of 838 restricted stock units, the company withheld 301 shares at $2.26 per share to satisfy his tax withholding obligation, which is a routine non-market disposition. After these transactions, he directly holds 146,515 shares, including 52,514 unvested RSUs.