According to recent filings covering the 90 days ending February 19, 2026, the three most significant insider holders at Skillz are Chief Executive Officer Andrew Paradise (1.36Mn shares), Director Casey Chafkin (787.38K shares), Director Christopher S Gaffney (706.37K shares).
| Holder | Position | Shares | Report Date |
|---|---|---|---|
| Christopher S Gaffney | 706,368 | 10 Mar, 2022 | |
| Miriam Aguirre | Chief Technology Officer | 79,994 | 09 Nov, 2021 |
| Andrew Paradise | Chief Executive Officer | 1,355,577 | 09 Jan, 2026 |
| Casey Chafkin | 787,385 | 23 Dec, 2025 | |
| Harry Sloan | 14,571 | 15 Mar, 2022 | |
| Charlotte Edelman | General Counsel And Secretary | 14,015 | 16 May, 2023 |
| Ian J Lee | Chief Financial Officer | 7,914 | 23 Jun, 2022 |
| Jerome Leon Bruckheimer | 6,655 | 09 Mar, 2022 | |
| Doris Fritz-Bianchi | Head Of People | 5,623 | 09 Sep, 2022 |
| Gaetano Franceschi | Chief Financial Officer | 107,080 | 09 Jan, 2026 |
| Jason Roswig | President & Cfo | 100,623 | 13 Nov, 2023 |
| Kevin Chessen | 2,500 | 06 Jun, 2023 | |
| Vandana Mehta-Krantz | 2,393 | 04 Jan, 2023 | |
| Stanley Mbugua | Chief Accounting Officer | 2,331 | 29 Mar, 2023 |
| Anthony Cabot | 19,048 | 23 Dec, 2025 | |
| Kent Wakeford | 18,302 | 23 Dec, 2025 | |
| Alexander Mandel | 14,134 | 23 Dec, 2025 | |
| Seth Schorr | 12,467 | 06 Sep, 2024 | |
| Henry M. Hoffman | 10,532 | 23 Dec, 2025 | |
| Salvatore Jr. Lento | Controller | 6,855 | 19 Nov, 2024 |
* 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 |
|---|---|---|---|---|---|---|---|---|
| 08 Jan, 2026 | Andrew Paradise | Class A common stock | A | 23,810 | $0.00 | 1,361,375 | D | M |
| 08 Jan, 2026 | Andrew Paradise | Class A common stock | A | 90,576 | $0.00 | 1,359,621 | D | M |
| 08 Jan, 2026 | Andrew Paradise | Class A common stock | D | 22,056 | $4.41 | 1,337,565 | D | F |
| 08 Jan, 2026 | Andrew Paradise | Class A common stock | D | 5,798 | $4.41 | 1,355,577 | D | F |
| 08 Jan, 2026 | Gaetano Franceschi | Class A common stock | D | 4,638 | $4.41 | 107,080 | D | F |
| 08 Jan, 2026 | Gaetano Franceschi | Class A common stock | A | 19,048 | $0.00 | 111,718 | D | M |
| 07 Jan, 2026 | Andrew Paradise | Class A common stock | D | 9,370 | $6.82 | 1,278,415 | D | F |
| 07 Jan, 2026 | Andrew Paradise | Class A common stock | D | 9,370 | $4.50 | 1,287,785 | D | F |
| 07 Jan, 2026 | Andrew Paradise | Class A common stock | D | 9,370 | $8.00 | 1,269,045 | D | F |
| 07 Jan, 2026 | Gaetano Franceschi | Class A common stock | D | 4,639 | $6.82 | 97,308 | D | F |
| 07 Jan, 2026 | Gaetano Franceschi | Class A common stock | D | 4,638 | $8.00 | 92,670 | D | F |
| 07 Jan, 2026 | Gaetano Franceschi | Class A common stock | D | 4,639 | $4.50 | 101,947 | D | F |
| 23 Dec, 2025 | Andrew Paradise | Class A common stock | D | 35,642 | $8.00 | 1,332,797 | D | F |
| 23 Dec, 2025 | Andrew Paradise | Class A common stock | D | 35,642 | $4.50 | 1,297,155 | D | F |
| 23 Dec, 2025 | Andrew Paradise | Class A common stock | D | 35,642 | $5.03 | 1,404,081 | D | F |
| 23 Dec, 2025 | Andrew Paradise | Class A common stock | D | 35,642 | $6.82 | 1,368,439 | D | F |
| 23 Dec, 2025 | Gaetano Franceschi | Class A common stock | D | 15,915 | $5.61 | 106,586 | D | F |
| 22 Dec, 2025 | Alexander Mandel | Class A common stock | A | 7,067 | $0.00 | 14,134 | D | M |
| 22 Dec, 2025 | Kent Wakeford | Class A common stock | A | 304 | $0.00 | 2,173 | D | M |
| 22 Dec, 2025 | Kent Wakeford | Class A common stock | A | 16,129 | $0.00 | 18,302 | D | M |