Skillz Inc. — Insider Transactions
Form 4 filings by directors, officers, and 10%+ shareholders
SEC rules require corporate insiders — including directors, executive officers, and any shareholder owning more than 10% of a company's shares — to report changes in their ownership within two business days of a transaction. These disclosures are filed as Form 4. Open-market purchases (code P) are generally considered the most meaningful signal, as insiders are spending their own money.
| Insider | Title | Type | Shares | Price | Value | Owns After | Date |
|---|---|---|---|---|---|---|---|
| Cabot Anthony | — | Option Exercise | 19,048 | — | — | 19,048 | Dec 22, 2025 |
| Hoffman Henry M. | — | Option Exercise | 3,510 | — | — | 10,532 | Dec 22, 2025 |
| Chafkin Casey | — | Option Exercise | 917 | — | — | 770,525 | Dec 22, 2025 |
| Wakeford Kent | — | Option Exercise | 16,129 | — | — | 18,302 | Dec 22, 2025 |
| Mandel Alexander | — | Option Exercise | 7,067 | — | — | 14,134 | Dec 22, 2025 |
| Paradise Andrew | Chief Executive Officer | Option Exercise | 71,430 | — | — | 1,077,422 | Dec 22, 2025 |
| Franceschi Gaetano | Chief Financial Officer | Option Exercise | 57,142 | — | — | 57,142 | Dec 22, 2025 |
| Chafkin Casey | — | Option Exercise | 916 | — | — | 769,608 | Dec 9, 2024 |
| Lento Salvatore Jr. | Controller | Sale | 2,157 | $5.02 | $10,828 | 6,855 | Nov 15, 2024 |
| Lento Salvatore Jr. | Controller | Option Exercise | 9,012 | — | — | 9,012 | Nov 14, 2024 |
| Paradise Andrew | Chief Executive Officer | Tax Withholding | 35,642 | $5.62 | $200,308 | 1,005,992 | Nov 13, 2024 |
| Paradise Andrew | Chief Executive Officer | Option Exercise | 90,576 | $5.62 | $509,037 | 1,077,276 | Nov 13, 2024 |
| Chafkin Casey | — | Option Exercise | 3,372 | — | — | 768,692 | Nov 13, 2024 |
| Chafkin Casey | — | Option Exercise | 916 | — | — | 765,320 | Sep 12, 2024 |
| Paradise Andrew | Chief Executive Officer | Tax Withholding | 28,514 | $6.02 | $171,654 | 841,190 | Sep 6, 2024 |
| Paradise Andrew | Chief Executive Officer | Option Exercise | 72,461 | — | — | 869,704 | Sep 6, 2024 |
| Chafkin Casey | — | Option Exercise | 3,372 | — | — | 764,404 | Sep 4, 2024 |
| Schorr Seth | — | Option Exercise | 3,116 | — | — | 12,467 | Sep 4, 2024 |
| Hoffman Henry M. | — | Option Exercise | 3,511 | — | — | 7,022 | Sep 4, 2024 |
| Chafkin Casey | Chief Strategy Officer | Option Exercise | 3,372 | — | — | 760,116 | Mar 14, 2024 |
| Chafkin Casey | Chief Strategy Officer | Option Exercise | 916 | — | — | 756,744 | Mar 4, 2024 |
| Mandel Alexander | — | Option Exercise | 7,067 | — | — | 7,067 | Jan 20, 2024 |
| Wakeford Kent | — | Option Exercise | 304 | — | — | 1,869 | Dec 18, 2023 |
| Chafkin Casey | Chief Strategy Officer | Option Exercise | 3,372 | — | — | 755,828 | Dec 14, 2023 |
| Chafkin Casey | Chief Strategy Officer | Option Exercise | 916 | — | — | 752,456 | Dec 5, 2023 |
| Roswig Jason | President & CFO | Option Exercise | 32,538 | — | — | 117,817 | Nov 10, 2023 |
| Chafkin Casey | Chief Strategy Officer | Option Exercise | 3,372 | — | — | 751,540 | Sep 18, 2023 |
| Chafkin Casey | Chief Strategy Officer | Option Exercise | 916 | — | — | 748,168 | Sep 5, 2023 |
| Schorr Seth | — | Option Exercise | 3,116 | — | — | 9,351 | Aug 28, 2023 |
| Roswig Jason | President & CFO | Sale | 44,872 | $10.03 | $450,066 | 85,279 | Aug 8, 2023 |
| Chafkin Casey | Chief Strategy Officer | Option Exercise | 87,805 | $1.00 | $87,805 | 747,252 | Aug 8, 2023 |
| Paradise Andrew | Chief Executive Officer | Purchase | 75,000 | $10.17 | $762,750 | 597,832 | Aug 7, 2023 |
| Hoffman Henry M. | — | Option Exercise | 3,511 | — | — | 3,511 | Aug 3, 2023 |
| Chafkin Casey | Chief Strategy Officer | Option Exercise | 67,450 | — | — | 13,188,951 | Jun 14, 2023 |
| Chessen Kevin | — | Purchase | 50,000 | $0.50 | $25,000 | 50,000 | Jun 5, 2023 |
| Chafkin Casey | Chief Strategy Officer | Option Exercise | 18,323 | — | — | 13,121,501 | Jun 4, 2023 |
| Edelman Charlotte | General Counsel and Secretary | Option Exercise | 29,976 | — | — | 280,293 | May 16, 2023 |
| Paradise Andrew | Chief Executive Officer | Purchase | 157,344 | $0.55 | $86,539 | 10,456,647 | May 12, 2023 |
| Paradise Andrew | Chief Executive Officer | Purchase | 1,500,000 | $0.56 | $840,000 | 8,956,647 | Apr 5, 2023 |
| Mbugua Stanley | Chief Accounting Officer | Option Exercise | 8,515 | — | — | 46,629 | Mar 27, 2023 |
| Chafkin Casey | Chief Revenue Officer | Option Exercise | 269,800 | — | — | 13,103,178 | Mar 14, 2023 |
| Chafkin Casey | Chief Revenue Officer | Option Exercise | 18,323 | — | — | 12,833,378 | Mar 4, 2023 |
| Edelman Charlotte | VP of Legal and Secretary | Option Exercise | 119,904 | — | — | 250,317 | Mar 1, 2023 |
| Wakeford Kent | — | Option Exercise | 25,236 | — | — | 31,316 | Jan 1, 2023 |
| Mehta-Krantz Vandana | — | Option Exercise | 25,236 | — | — | 47,859 | Jan 1, 2023 |
| Mbugua Stanley | Chief Accounting Officer | Option Exercise | 8,515 | — | — | 38,114 | Dec 27, 2022 |
| Mehta-Krantz Vandana | — | Award / Grant | 6,080 | — | — | 22,623 | Dec 16, 2022 |
| Wakeford Kent | — | Award / Grant | 6,080 | — | — | 6,080 | Dec 16, 2022 |
| Chafkin Casey | Chief Revenue Officer | Option Exercise | 18,323 | — | — | 12,815,055 | Dec 4, 2022 |
| Mbugua Stanley | Chief Accounting Officer | Sale | 10,620 | $1.07 | $11,363 | 29,290 | Sep 27, 2022 |