As of September 29, 2026, Lemonade's top three insider holders are Group Capital Ltd Softbank (TenPercentOwner, 7.11Mn shares), Shai Wininger (President, 4.42Mn shares), Daniel A. Schreiber (Chief Executive Officer, 1.51Mn shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Group Capital Ltd Softbank | TenPercentOwner | 7,111,441 | 0 | 7,111,441 | 51.7% | 14 May, 2025 |
| 2 | Shai Wininger | President | 4,416,873 | 0 | 4,416,873 | 32.1% | 04 Sep, 2026 |
| 3 | Daniel A. Schreiber | Chief Executive Officer | 1,024,327 | 0 | 1,024,327 | 7.4% | 20 Mar, 2026 |
| 4 | Adina Eckstein | Chief Operating Officer | 333,503 | 0 | 333,503 | 2.4% | 10 Mar, 2026 |
| 5 | Michael A Eisenberg | Director | 290,122 | 0 | 290,122 | 2.1% | 12 Jun, 2026 |
| 6 | Maya Prosor | Chief Business Officer | 186,533 | 0 | 186,533 | 1.4% | 08 Sep, 2026 |
| 7 | Timothy E Bixby | Chief Financial Officer | 172,370 | 0 | 172,370 | 1.3% | 08 Sep, 2026 |
| 8 | John Sheldon Peters | Chief Insurance Officer | 73,834 | 0 | 73,834 | 0.5% | 08 Sep, 2026 |
| 9 | Samer Haj-Yehia | Director | 27,187 | 0 | 27,187 | 0.2% | 05 Jun, 2026 |
| 10 | Debra Schwartz | Director | 24,415 | 0 | 24,415 | 0.2% | 05 Jun, 2026 |
| 11 | Mwashuma Kamata Nyatta | Director | 23,189 | 0 | 23,189 | 0.2% | 26 Jun, 2024 |
| 12 | Irina Novoselsky | Director | 18,462 | 0 | 18,462 | 0.1% | 09 Jun, 2023 |
| 13 | Silvija Martincevic | Director | 18,462 | 0 | 18,462 | 0.1% | 09 Jun, 2023 |
| 14 | Maria Angelidis-Smith | Director | 17,744 | 0 | 17,744 | 0.1% | 05 Jun, 2026 |
| 15 | Prashant Ratanchandani | Director | 6,185 | 0 | 6,185 | 0.0% | 05 Jun, 2026 |
| 16 | Geoff Seeley | Director | 5,967 | 0 | 5,967 | 0.0% | 05 Jun, 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 |
|---|---|---|---|---|---|---|---|---|
| 03 Sep, 2026 | Maya Prosor | Chief Business Officer | Disposed S | 1,040 | $54.63 | $56.82K | 186,533 | Direct |
| 03 Sep, 2026 | John Sheldon Peters | Chief Insurance Officer | Disposed S | 859 | $54.63 | $46.93K | 76,083 | Direct |
| 03 Sep, 2026 | Timothy E Bixby | Chief Financial Officer | Disposed S | 1,893 | $54.63 | $103.41K | 172,370 | Direct |
| 04 Sep, 2026 | John Sheldon Peters | Chief Insurance Officer | Disposed S | 2,249 | $54.45 | $122.46K | 73,834 | Direct |
| 02 Sep, 2026 | Shai Wininger | President | Disposed G | 1,876 | $0.00 | $0 | 4,416,873 | Direct |
| 13 Aug, 2026 | John Sheldon Peters | Chief Insurance Officer | Disposed S | 11,000 | $52.55 | $578.05K | 76,942 | Direct |
| 27 Jul, 2026 | John Sheldon Peters | Chief Insurance Officer | Acquired A | 10,000 | $0.00 | $0 | 87,942 | Direct |
| 07 Jul, 2026 | Timothy E Bixby | Chief Financial Officer | Disposed S | 73,000 | $79.18 | $5.78Mn | 174,263 | Direct |
| 06 Jul, 2026 | John Sheldon Peters | Chief Insurance Officer | Disposed S | 3,444 | $79.00 | $272.08K | 77,942 | Direct |
| 10 Jun, 2026 | Michael A Eisenberg | Director | Disposed G | 5,000 | $0.00 | $0 | 195,452 | Direct |
| 03 Jun, 2026 | Maria Angelidis-Smith | Director | Acquired A | 2,848 | $0.00 | $0 | 17,744 | Direct |
| 03 Jun, 2026 | Debra Schwartz | Director | Acquired A | 2,848 | $0.00 | $0 | 24,415 | Direct |
| 03 Jun, 2026 | Geoff Seeley | Director | Acquired A | 2,848 | $0.00 | $0 | 5,967 | Direct |
| 03 Jun, 2026 | John Sheldon Peters | Chief Insurance Officer | Disposed S | 1,735 | $53.17 | $92.25K | 84,994 | Direct |
| 03 Jun, 2026 | Timothy E Bixby | Chief Financial Officer | Disposed S | 2,227 | $53.17 | $118.41K | 247,263 | Direct |
| 03 Jun, 2026 | Prashant Ratanchandani | Director | Acquired A | 2,848 | $0.00 | $0 | 6,185 | Direct |
| 03 Jun, 2026 | Maya Prosor | Chief Business Officer | Disposed S | 1,220 | $53.17 | $64.87K | 187,573 | Direct |
| 03 Jun, 2026 | Samer Haj-Yehia | Director | Acquired A | 2,848 | $0.00 | $0 | 27,187 | Direct |
| 04 Jun, 2026 | John Sheldon Peters | Chief Insurance Officer | Disposed S | 3,608 | $52.94 | $191.01K | 81,386 | Direct |
| 10 Mar, 2026 | Maria Angelidis-Smith | Director | Acquired P | 3,350 | $55.30 | $185.26K | 14,896 | Direct |