System1's top three insider shareholders as of April 28, 2026 are Christopher Stephen Phillips (Director, 29.38Mn shares), Holdings, Inc. Cannae (TenPercentOwner, 27.01Mn shares), Holdings, Inc. Cannae (TenPercentOwner, 26.40Mn shares).
| Holder | Position | Shares (Direct) | Shares (Indirect) | Report Date |
|---|---|---|---|---|
| Christopher Stephen Phillips | - | 0 | 29,375,499 | 01 Feb, 2022 |
| Holdings, Inc. Cannae | - | 0 | 27,012,794 | 07 Sep, 2023 |
| Holdings, Inc. Cannae | - | 0 | 26,402,297 | 26 Apr, 2022 |
| Holdings, Inc. Cannae | - | 0 | 25,749,405 | 03 May, 2022 |
| Holdings, Inc. Cannae | - | 0 | 25,666,724 | 19 May, 2022 |
| Christopher Stephen Phillips | - | 0 | 18,672,586 | 09 Sep, 2022 |
| Stanley Blend | - | 0 | 8,477,861 | 18 Dec, 2023 |
| L Michael Blend | - | 0 | 8,448,338 | 01 Feb, 2022 |
| Trebia, Lp Trasimene | - | 6,601,898 | 0 | 20 Apr, 2022 |
| Star Friends Trust Lone | - | 5,731,423 | 0 | 09 Dec, 2022 |
| Star Friends Trust Lone | - | 5,731,423 | 0 | 09 Dec, 2022 |
| L Michael Blend | - | 0 | 5,447,175 | 01 Feb, 2022 |
| Trebia Lp Bgpt | - | 4,450,879 | 0 | 20 Apr, 2022 |
| Stanley Blend | - | 0 | 3,035,243 | 14 Aug, 2024 |
| Stanley Blend | - | 0 | 2,500,000 | 27 Dec, 2024 |
| Star Friends Trust Lone | - | 0 | 1,850,215 | 26 Jun, 2024 |
| Star Friends Trust Lone | - | 0 | 1,850,215 | 26 Jun, 2024 |
| Christopher Stephen Phillips | - | 0 | 939,541 | 21 Apr, 2022 |
| Holdings Trust Cee | - | 919,555 | 0 | 26 Aug, 2025 |
| Develop It Ltd Just | - | 725,000 | 0 | 07 Mar, 2022 |
| Christopher Stephen Phillips | - | 0 | 725,000 | 07 Mar, 2022 |
| Paul Filsinger | President | 540,868 | 0 | 02 Feb, 2022 |
| Paul Filsinger | President | 459,399 | 0 | 17 Oct, 2022 |
| Tridivesh Kidambi | - | 436,093 | 0 | 02 Feb, 2022 |
| Charles Ursini | President Coo | 367,500 | 0 | 31 Jul, 2025 |
| Charles Ursini | President Coo | 367,500 | 0 | 31 Jul, 2025 |
| Brian Coppola | Chief Product Officer | 225,969 | 0 | 02 Feb, 2022 |
| Jennifer Mindy Prince | - | 222,433 | 0 | 13 Jun, 2024 |
| William Dexter Fowler | - | 218,433 | 0 | 13 Jun, 2024 |
| Elizabeth Sestanovich | Chief People Officer | 208,595 | 0 | 02 Feb, 2022 |
| Jennifer Lynn Robinson | Chief Technology Officer | 161,943 | 0 | 20 Aug, 2024 |
| Christopher Stephen Phillips | - | 160,000 | 0 | 03 Aug, 2023 |
| Tridivesh Kidambi | Chief Financial Officer | 146,515 | 0 | 17 Apr, 2026 |
| Moujan Kazerani | - | 0 | 75,612 | 01 Feb, 2022 |
| John Civantos | - | 70,613 | 0 | 05 Aug, 2025 |
| Daniel J Weinrot | General Counsel Secretary | 69,394 | 0 | 29 Jan, 2026 |
| Daniel J Weinrot | General Counsel Secretary | 69,053 | 0 | 17 Apr, 2026 |
| Brian Coppola | Chief Ad Operations Officer | 65,898 | 0 | 17 Apr, 2026 |
| Daniel J Weinrot | General Counsel | 59,642 | 0 | 31 Jan, 2022 |
| Daniel J Weinrot | General Counsel | 59,642 | 0 | 31 Jan, 2022 |
| Elizabeth Sestanovich | Chief People Officer | 58,948 | 0 | 17 Apr, 2026 |
| Frank R Martire | - | 41,575 | 0 | 04 Aug, 2025 |
| Moujan Kazerani | - | 40,292 | 0 | 04 Aug, 2025 |
| Ryan R. Caswell | - | 38,577 | 0 | 04 Aug, 2025 |
| Taryn Jogi Naidu | - | 38,562 | 0 | 04 Aug, 2025 |
| Caroline Horn | - | 37,418 | 0 | 04 Aug, 2025 |
| Tanmay Kumar | - | 35,196 | 0 | 04 Aug, 2025 |
| Frank R Martire | - | 32,000 | 0 | 12 May, 2022 |
| William P Ii Foley | - | 24,000 | 0 | 12 May, 2022 |
| Moujan Kazerani | - | 0 | 20,500 | 07 Mar, 2022 |
| Tridivesh Kidambi | Chief Financial Officer | 0 | 15,518 | 07 Mar, 2022 |
* Please note that the shares above only reflect shares from the fund portfolio and the institutional portfolio. Shares from the personal portfolio are excluded from this Institutional Ownership Page. See these insiders' latest transactions here on Insider Page.
| Transaction Date | Insider Name | Security Class | Transaction Type | Shares Traded | Price | Shares Remaining | Ownership | Code |
|---|---|---|---|---|---|---|---|---|
| 15 Apr, 2026 | Tridivesh Kidambi | Class A Common Stock | A | 26,910 | $3.00 | 146,816 | D | P |
| 15 Apr, 2026 | Elizabeth Sestanovich | Class A Common Stock | D | 341 | $2.26 | 58,948 | D | F |
| 15 Apr, 2026 | Daniel J Weinrot | Class A Common Stock | D | 341 | $2.26 | 69,053 | D | F |
| 15 Apr, 2026 | Brian Coppola | Class A Common Stock | D | 331 | $2.26 | 65,898 | D | F |
| 15 Apr, 2026 | Tridivesh Kidambi | Class A Common Stock | D | 301 | $2.26 | 146,515 | D | F |
| 28 Jan, 2026 | Daniel J Weinrot | Class A Common Stock | D | 211 | $4.18 | 69,394 | D | F |
| 28 Jan, 2026 | Elizabeth Sestanovich | Class A Common Stock | D | 211 | $4.18 | 59,289 | D | F |
| 28 Jan, 2026 | Tridivesh Kidambi | Class A Common Stock | D | 258 | $4.18 | 119,906 | D | F |
| 28 Jan, 2026 | Daniel J Weinrot | Class A Common Stock | D | 211 | $4.18 | 69,394 | D | F |
| 28 Jan, 2026 | Brian Coppola | Class A Common Stock | D | 231 | $4.18 | 66,229 | D | F |
| 15 Jan, 2026 | Tridivesh Kidambi | Class A Common Stock | D | 345 | $4.40 | 120,164 | D | F |
| 15 Jan, 2026 | Elizabeth Sestanovich | Class A Common Stock | D | 377 | $4.40 | 59,500 | D | F |
| 15 Jan, 2026 | Daniel J Weinrot | Class A Common Stock | D | 377 | $4.40 | 69,605 | D | F |
| 15 Jan, 2026 | Brian Coppola | Class A Common Stock | D | 371 | $4.40 | 66,460 | D | F |
| 15 Jan, 2026 | Daniel J Weinrot | Class A Common Stock | D | 377 | $4.40 | 69,605 | D | F |
| 28 Oct, 2025 | Daniel J Weinrot | Class A Common Stock | D | 214 | $6.18 | 69,982 | D | F |
| 28 Oct, 2025 | Daniel J Weinrot | Class A Common Stock | D | 214 | $6.18 | 69,982 | D | F |
| 28 Oct, 2025 | Brian Coppola | Class A Common Stock | D | 235 | $6.18 | 66,831 | D | F |
| 28 Oct, 2025 | Tridivesh Kidambi | Class A Common Stock | D | 263 | $6.18 | 120,509 | D | F |
| 28 Oct, 2025 | Elizabeth Sestanovich | Class A Common Stock | D | 158 | $6.18 | 59,877 | D | F |