As of September 09, 2026, Tiptree's top three insider holders are Michael Gene Barnes (Executive Chairman, 10.09Mn shares), Arif Inayatullah (TenPercentOwner, 3.59Mn shares), Jonathan Ilany (Chief Executive Officer, 274.74K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Michael Gene Barnes | Executive Chairman | 10,085,428 | 0 | 10,085,428 | 70.2% | 12 Sep, 2025 |
| 2 | Arif Inayatullah | TenPercentOwner | 3,592,419 | 0 | 3,592,419 | 25.0% | 09 Feb, 2023 |
| 3 | Jonathan Ilany | Chief Executive Officer | 0 | 193,011 | 193,011 | 1.3% | 28 May, 2026 |
| 4 | Paul M Friedman | Director | 0 | 122,398 | 122,398 | 0.9% | 09 Jan, 2026 |
| 5 | Lesley Goldwasser | Director | 114,410 | 0 | 114,410 | 0.8% | 09 Jan, 2026 |
| 6 | Bradley E. Smith | Director | 107,263 | 0 | 107,263 | 0.7% | 06 Jul, 2026 |
| 7 | Dominique Mielle | Director | 70,712 | 0 | 70,712 | 0.5% | 10 Nov, 2025 |
| 8 | Randy Maultsby | President | 47,244 | 0 | 47,244 | 0.3% | 11 Oct, 2024 |
| 9 | Neil Charles Rifkind | General Counsel And Secretary | 15,660 | 0 | 15,660 | 0.1% | 26 Mar, 2025 |
| 10 | Sandra Bell | Chief Financial Officer | 5,335 | 0 | 5,335 | 0.0% | 14 Nov, 2022 |
| 11 | Scott T. Mckinney | Chief Financial Officer | 0 | 4,000 | 4,000 | 0.0% | 13 Mar, 2026 |
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 |
|---|---|---|---|---|---|---|---|---|
| 02 Jul, 2026 | Bradley E. Smith | Director | Acquired A | 1,768 | $0.00 | $0 | 107,263 | Direct |
| 02 Jul, 2026 | Lesley Goldwasser | Director | Acquired A | 1,061 | $0.00 | $0 | 116,615 | Direct |
| 27 May, 2026 | Jonathan Ilany | Director | Acquired P | 990 | $17.45 | $17.28K | 193,011 | Indirect |
| 02 Apr, 2026 | Bradley E. Smith | Director | Acquired A | 1,907 | $0.00 | $0 | 105,495 | Direct |
| 02 Apr, 2026 | Lesley Goldwasser | Director | Acquired A | 1,144 | $0.00 | $0 | 115,554 | Direct |
| 11 Mar, 2026 | Scott T. Mckinney | Chief Financial Officer | Acquired P | 2,600 | $16.15 | $42.00K | 2,768 | Indirect |
| 12 Mar, 2026 | Scott T. Mckinney | Chief Financial Officer | Acquired P | 1,232 | $15.98 | $19.68K | 4,000 | Indirect |
| 20 Feb, 2026 | Scott T. Mckinney | Chief Financial Officer | Acquired M | 15,110 | — | — | 105,082 | Direct |
| 20 Feb, 2026 | Scott T. Mckinney | Chief Financial Officer | Disposed F | 5,143 | $17.06 | $87.74K | 99,939 | Direct |
| 20 Feb, 2026 | Scott T. Mckinney | Chief Financial Officer | Disposed M | 15,110 | — | — | 0 | Direct |
| 08 Jan, 2026 | Paul M Friedman | Director | Acquired A | 2,048 | $0.00 | $0 | 122,398 | Indirect |
| 08 Jan, 2026 | Lesley Goldwasser | Director | Acquired A | 2,048 | $0.00 | $0 | 114,410 | Direct |
| 07 Nov, 2025 | Dominique Mielle | Director | Acquired P | 5,500 | $18.29 | $100.60K | 70,712 | Direct |
| 03 Oct, 2025 | Lesley Goldwasser | Director | Acquired A | 1,807 | $0.00 | $0 | 112,362 | Direct |
| 03 Oct, 2025 | Paul M Friedman | Director | Acquired A | 1,807 | $0.00 | $0 | 120,350 | Indirect |
| 15 Sep, 2025 | Jonathan Ilany | Chief Executive Officer | Acquired M | 351,155 | $6.65 | $2.34Mn | 498,060 | Direct |
| 15 Sep, 2025 | Jonathan Ilany | Chief Executive Officer | Disposed F | 98,531 | $23.70 | $2.34Mn | 399,529 | Direct |
| 15 Sep, 2025 | Jonathan Ilany | Chief Executive Officer | Disposed F | 124,787 | $23.70 | $2.96Mn | 274,742 | Direct |
| 15 Sep, 2025 | Jonathan Ilany | Chief Executive Officer | Disposed M | 351,155 | $6.65 | $2.34Mn | 0 | Direct |
| 12 Sep, 2025 | Michael Gene Barnes | Executive Chairman | Acquired M | 46,494 | $5.67 | $263.62K | 10,009,402 | Direct |