System1's three largest insider shareholders as of September 29, 2026 are Holdings, Inc. Cannae (TenPercentOwner, 7.78Mn shares), Christopher Stephen Phillips (Director, 3.01Mn shares), Holdings, Inc. Cannae (TenPercentOwner, 2.70Mn shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Holdings, Inc. Cannae | TenPercentOwner | 0 | 2,701,279 | 2,701,279 | 33.3% | 07 Sep, 2023 |
| 2 | L Michael Blend | Director, Officer, TenPercentOwner | 0 | 1,389,551 | 1,389,551 | 17.1% | 01 Feb, 2022 |
| 3 | Stanley Blend | TenPercentOwner | 0 | 1,097,786 | 1,097,786 | 13.5% | 27 Dec, 2024 |
| 4 | Holdings Trust Cee | TenPercentOwner | 919,555 | 0 | 919,555 | 11.3% | 26 Aug, 2025 |
| 5 | Trebia Lp Bgpt | Director, TenPercentOwner | 445,088 | 0 | 445,088 | 5.5% | 20 Apr, 2022 |
| 6 | Charles Ursini | President Coo | 367,500 | 0 | 367,500 | 4.5% | 31 Jul, 2025 |
| 7 | Tridivesh Kidambi | Chief Financial Officer | 219,402 | 0 | 219,402 | 2.7% | 17 Jul, 2026 |
| 8 | Star Friends Trust Lone | TenPercentOwner | 0 | 185,022 | 185,022 | 2.3% | 26 Jun, 2024 |
| 9 | Paul Filsinger | President | 100,027 | 0 | 100,027 | 1.2% | 17 Oct, 2022 |
| 10 | Brian Coppola | Chief Ad Operations Officer | 82,371 | 0 | 82,371 | 1.0% | 17 Jul, 2026 |
| 11 | Elizabeth Sestanovich | Chief People Officer | 72,750 | 0 | 72,750 | 0.9% | 17 Jul, 2026 |
| 12 | Develop It Ltd Just | TenPercentOwner | 72,500 | 0 | 72,500 | 0.9% | 07 Mar, 2022 |
| 13 | John Civantos | Director | 70,613 | 0 | 70,613 | 0.9% | 05 Aug, 2025 |
| 14 | Daniel J Weinrot | General Counsel Secretary | 65,861 | 0 | 65,861 | 0.8% | 17 Jul, 2026 |
| 15 | Frank R Martire | Director | 44,775 | 0 | 44,775 | 0.6% | 04 Aug, 2025 |
| 16 | Moujan Kazerani | Director | 40,292 | 0 | 40,292 | 0.5% | 04 Aug, 2025 |
| 17 | Ryan R. Caswell | Director | 38,577 | 0 | 38,577 | 0.5% | 04 Aug, 2025 |
| 18 | Taryn Jogi Naidu | Director | 38,562 | 0 | 38,562 | 0.5% | 04 Aug, 2025 |
| 19 | Caroline Horn | Director | 37,418 | 0 | 37,418 | 0.5% | 04 Aug, 2025 |
| 20 | Tanmay Kumar | Director | 35,196 | 0 | 35,196 | 0.4% | 04 Aug, 2025 |
| 21 | Jennifer Mindy Prince | Director | 22,243 | 0 | 22,243 | 0.3% | 13 Jun, 2024 |
| 22 | William Dexter Fowler | Director | 21,843 | 0 | 21,843 | 0.3% | 13 Jun, 2024 |
| 23 | Jennifer Lynn Robinson | Chief Technology Officer | 16,194 | 0 | 16,194 | 0.2% | 20 Aug, 2024 |
| 24 | Christopher Stephen Phillips | Director, TenPercentOwner | 16,000 | 0 | 16,000 | 0.2% | 03 Aug, 2023 |
| 25 | William P Ii Foley | Director, TenPercentOwner | 2,400 | 0 | 2,400 | 0.0% | 12 May, 2022 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 15 Jul, 2026 | Elizabeth Sestanovich | Chief People Officer | Disposed F | 7,058 | $2.60 | $18.35K | 51,890 | Direct |
| 15 Jul, 2026 | Tridivesh Kidambi | Chief Financial Officer | Disposed F | 6,022 | $2.60 | $15.66K | 175,793 | Direct |
| 15 Jul, 2026 | Daniel J Weinrot | General Counsel Secretary | Disposed F | 9,156 | $2.60 | $23.81K | 59,897 | Direct |
| 15 Jul, 2026 | Brian Coppola | Chief Ad Operations Officer | Disposed F | 6,124 | $2.60 | $15.92K | 59,774 | Direct |
| 29 May, 2026 | Tridivesh Kidambi | Chief Financial Officer | Acquired A | 35,300 | $0.00 | $0 | 181,815 | Direct |
| 15 Apr, 2026 | Brian Coppola | Chief Ad Operations Officer | Disposed F | 331 | $2.26 | $748 | 65,898 | Direct |
| 15 Apr, 2026 | Daniel J Weinrot | General Counsel Secretary | Disposed F | 341 | $2.26 | $771 | 69,053 | Direct |
| 15 Apr, 2026 | Tridivesh Kidambi | Chief Financial Officer | Acquired P | 26,910 | $3.00 | $80.73K | 146,816 | Direct |
| 15 Apr, 2026 | Elizabeth Sestanovich | Chief People Officer | Disposed F | 341 | $2.26 | $771 | 58,948 | Direct |
| 15 Apr, 2026 | Tridivesh Kidambi | Chief Financial Officer | Disposed F | 301 | $2.26 | $680 | 146,515 | Direct |
| 28 Jan, 2026 | Tridivesh Kidambi | Chief Financial Officer | Disposed F | 258 | $4.18 | $1.08K | 119,906 | Direct |
| 28 Jan, 2026 | Brian Coppola | Chief Ad Operations Officer | Disposed F | 231 | $4.18 | $966 | 66,229 | Direct |
| 28 Jan, 2026 | Daniel J Weinrot | General Counsel Secretary | Disposed F | 211 | $4.18 | $882 | 69,394 | Direct |
| 28 Jan, 2026 | Elizabeth Sestanovich | Chief People Officer | Disposed F | 211 | $4.18 | $882 | 59,289 | Direct |
| 15 Jan, 2026 | Daniel J Weinrot | General Counsel Secretary | Disposed F | 377 | $4.40 | $1.66K | 69,605 | Direct |
| 15 Jan, 2026 | Elizabeth Sestanovich | Chief People Officer | Disposed F | 377 | $4.40 | $1.66K | 59,500 | Direct |
| 15 Jan, 2026 | Brian Coppola | Chief Ad Operations Officer | Disposed F | 371 | $4.40 | $1.63K | 66,460 | Direct |
| 15 Jan, 2026 | Tridivesh Kidambi | Chief Financial Officer | Disposed F | 345 | $4.40 | $1.52K | 120,164 | Direct |
| 28 Oct, 2025 | Tridivesh Kidambi | Chief Financial Officer | Disposed F | 263 | $6.18 | $1.63K | 120,509 | Direct |
| 28 Oct, 2025 | Daniel J Weinrot | General Counsel Secretary | Disposed F | 214 | $6.18 | $1.32K | 69,982 | Direct |