| Thu, 1 Oct 2026 | DELANEY KEVIN M | officer: Chief Accounting Officer | F-InKind | 959 | $12.91K |
| Fri, 2 Oct 2026 | Chafey Diana | officer: Chief Legal Officer | A-Award | 979 | $12.52K |
| Fri, 2 Oct 2026 | McClymont Patrick | officer: Chief Financial Officer | A-Award | 1,192 | $15.25K |
| Thu, 1 Oct 2026 | Chafey Diana | officer: Chief Legal Officer | F-InKind | 1,076 | $14.48K |
| Thu, 24 Sep 2026 | KAUFFMAN ROBERT I | director | G-Gift | 74,000 | $0 |
| Fri, 11 Sep 2026 | MARKEL GROUP INC. | 10 percent owner | C-Conversion | 7,836,411 | — |
| Wed, 9 Sep 2026 | Hagerty Holding Corp. | 10 percent owner | S-Sale | 9,250,000 | $106.12M |
| Wed, 9 Sep 2026 | Hagerty Holding Corp. | 10 percent owner | C-Conversion | 9,250,000 | — |
| Fri, 11 Sep 2026 | Hagerty Holding Corp. | 10 percent owner | S-Sale | 1,387,500 | $15.92M |
| Fri, 11 Sep 2026 | Hagerty Holding Corp. | 10 percent owner | C-Conversion | 1,387,500 | — |
| Thu, 2 Jul 2026 | DELANEY KEVIN M | officer: Chief Accounting Officer | S-Sale | 3,113 | $38.13K |
| Wed, 1 Jul 2026 | Briglia Jeffrey Edward | officer: President of Insurance | F-InKind | 4,892 | $59K |
| Wed, 1 Jul 2026 | Bjornstad Henrik Waersted | director | A-Award | 10,114 | $0 |
| Wed, 1 Jul 2026 | DELANEY KEVIN M | officer: Chief Accounting Officer | F-InKind | 2,525 | $30.45K |
| Wed, 1 Jul 2026 | DELANEY KEVIN M | officer: Chief Accounting Officer | S-Sale | 9,440 | $114.22K |
| Tue, 30 Jun 2026 | DELANEY KEVIN M | officer: Chief Accounting Officer | S-Sale | 905 | $10.87K |
| Fri, 15 May 2026 | Kuczinski Anthony J | director | P-Purchase | 9,500 | $99.37K |
| Tue, 7 Apr 2026 | Harris Laurie | director | S-Sale | 5,531 | $60.9K |
| Wed, 1 Apr 2026 | Hagerty McKeel | director, officer: Chief Executive Officer | F-InKind | 82,868 | $883.37K |
| Wed, 1 Apr 2026 | Ahn Kenneth | officer: President, Hagerty Marketplace | F-InKind | 9,627 | $102.62K |
| Wed, 1 Apr 2026 | Ahn Kenneth | officer: President, Hagerty Marketplace | A-Award | 23,149 | $0 |
| Wed, 1 Apr 2026 | Kuczinski Anthony J | director | A-Award | 11,871 | $0 |
| Wed, 1 Apr 2026 | SWANSON WILLIAM H | director | A-Award | 11,871 | $0 |
| Wed, 1 Apr 2026 | KAUFFMAN ROBERT I | director | A-Award | 11,871 | $0 |
| Wed, 1 Apr 2026 | Harbert Randall Houston | director | A-Award | 11,871 | $0 |
| Wed, 1 Apr 2026 | Kay Sabrina | director | A-Award | 11,871 | $0 |
| Thu, 2 Apr 2026 | Chafey Diana | officer: Chief Legal Officer | A-Award | 1,165 | $11.8K |
| Thu, 2 Apr 2026 | McClymont Patrick | officer: Chief Financial Officer | A-Award | 962 | $9.75K |
| Wed, 1 Apr 2026 | Heaton Michael R | director | A-Award | 11,871 | $0 |
| Wed, 1 Apr 2026 | Harris Laurie | director | A-Award | 11,871 | $0 |
| Wed, 1 Apr 2026 | Briglia Jeffrey Edward | officer: President of Insurance | A-Award | 46,297 | $0 |
| Wed, 1 Apr 2026 | Briglia Jeffrey Edward | officer: President of Insurance | F-InKind | 9,899 | $105.52K |
| Wed, 1 Apr 2026 | DELANEY KEVIN M | officer: Chief Accounting Officer | F-InKind | 8,456 | $90.14K |
| Wed, 1 Apr 2026 | DELANEY KEVIN M | officer: Chief Accounting Officer | A-Award | 17,614 | $0 |
| Wed, 1 Apr 2026 | Chafey Diana | officer: Chief Legal Officer | F-InKind | 4,833 | $51.52K |
| Wed, 1 Apr 2026 | Chafey Diana | officer: Chief Legal Officer | A-Award | 23,742 | $0 |
| Wed, 1 Apr 2026 | Salmi Mika | director | A-Award | 11,871 | $0 |
| Wed, 1 Apr 2026 | Page Russell Andrew | officer: Chief Information Officer | F-InKind | 11,146 | $118.82K |
| Wed, 1 Apr 2026 | Page Russell Andrew | officer: Chief Information Officer | A-Award | 30,865 | $0 |
| Wed, 1 Apr 2026 | McClymont Patrick | officer: Chief Financial Officer | F-InKind | 32,388 | $345.26K |
| Wed, 1 Apr 2026 | McClymont Patrick | officer: Chief Financial Officer | A-Award | 54,013 | $0 |
| Wed, 1 Apr 2026 | Champagne Collette | officer: CHRO and CAO | A-Award | 23,742 | $0 |
| Wed, 1 Apr 2026 | Champagne Collette | officer: CHRO and CAO | F-InKind | 28,278 | $301.44K |
| Thu, 12 Mar 2026 | Kuczinski Anthony J | director | P-Purchase | 4,000 | $38K |
| Tue, 3 Mar 2026 | Kuczinski Anthony J | director | P-Purchase | 15,000 | $160.8K |
| Mon, 26 Jan 2026 | Ahn Kenneth | officer: President, Hagerty Marketplace | C-Conversion | 50,000 | $0 |
| Mon, 26 Jan 2026 | Ahn Kenneth | officer: President, Hagerty Marketplace | S-Sale | 50,000 | $620.5K |
| Tue, 20 Jan 2026 | Ahn Kenneth | officer: President, Hagerty Marketplace | C-Conversion | 50,000 | $0 |
| Tue, 20 Jan 2026 | Ahn Kenneth | officer: President, Hagerty Marketplace | S-Sale | 50,000 | $627.5K |
| Mon, 12 Jan 2026 | Ahn Kenneth | officer: President, Hagerty Marketplace | S-Sale | 50,000 | $643K |
