Lemonade's three largest insider shareholders as of March 23, 2026 are Group Capital Ltd Softbank (TenPercentOwner, 7.11Mn shares), Shai Wininger (President, 3.39Mn shares), Daniel A. Schreiber (Chief Executive Officer, 1.51Mn shares).
| Holder | Position | Shares (Direct) | Shares (Indirect) | Report Date |
|---|---|---|---|---|
| Group Capital Ltd Softbank | 7,111,441 | 0 | 14 May, 2025 | |
| Shai Wininger | President | 4,418,749 | 0 | 20 Mar, 2026 |
| Daniel A. Schreiber | Chief Executive Officer | 0 | 1,514,426 | 04 Feb, 2026 |
| Daniel A. Schreiber | Chief Executive Officer | 1,024,327 | 0 | 20 Mar, 2026 |
| Maya Prosor | Chief Business Officer | 188,793 | 0 | 10 Mar, 2026 |
| John Sheldon Peters | Chief Insurance Officer | 76,729 | 0 | 05 Mar, 2026 |
| Maria Angelidis-Smith | 14,896 | 38,944 | 12 Mar, 2026 | |
| Maya Prosor | Chief Business Officer | 0 | 29,286 | 25 Nov, 2024 |
| Mwashuma Kamata Nyatta | 23,189 | 0 | 26 Jun, 2024 | |
| Debra Schwartz | 21,567 | 0 | 15 Dec, 2025 | |
| Silvija Martincevic | 18,462 | 0 | 09 Jun, 2023 | |
| Irina Novoselsky | 18,462 | 0 | 09 Jun, 2023 | |
| Prashant Ratanchandani | 3,337 | 0 | 29 Oct, 2025 | |
| Geoff Seeley | 3,119 | 0 | 29 Oct, 2025 |
* 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 |
|---|---|---|---|---|---|---|---|---|
| 18 Mar, 2026 | Daniel A. Schreiber | COMMON STOCK | A | 820,000 | $0.00 | 844,327 | D | A |
| 18 Mar, 2026 | Shai Wininger | COMMON STOCK | A | 820,000 | $0.00 | 4,238,749 | D | A |
| 18 Mar, 2026 | Shai Wininger | COMMON STOCK | A | 180,000 | $0.00 | 4,418,749 | D | A |
| 18 Mar, 2026 | Daniel A. Schreiber | COMMON STOCK | A | 180,000 | $0.00 | 1,024,327 | D | A |
| 10 Mar, 2026 | Maria Angelidis-Smith | COMMON STOCK | A | 3,350 | $55.30 | 14,896 | D | A |
| 10 Mar, 2026 | Maria Angelidis-Smith | COMMON STOCK | A | 5,390 | $55.70 | 38,944 | I | A |
| 08 Mar, 2026 | Maya Prosor | COMMON STOCK | A | 181,389 | $0.00 | 188,793 | D | A |
| 03 Mar, 2026 | John Sheldon Peters | COMMON STOCK | D | 1,773 | $50.12 | 80,300 | D | S |
| 03 Mar, 2026 | Maya Prosor | COMMON STOCK | D | 223 | $50.12 | 7,404 | D | S |
| 04 Mar, 2026 | John Sheldon Peters | COMMON STOCK | D | 3,571 | $52.50 | 76,729 | D | S |
| 23 Jan, 2026 | Daniel A. Schreiber | COMMON STOCK | D | 9,108 | $99.04 | 1,514,426 | I | S |
| 22 Jan, 2026 | John Sheldon Peters | COMMON STOCK | D | 9,000 | $90.00 | 70,228 | D | S |
| 22 Jan, 2026 | Daniel A. Schreiber | COMMON STOCK | D | 126,625 | $94.74 | 1,523,534 | I | S |
| 08 Jan, 2026 | John Sheldon Peters | COMMON STOCK | A | 18,457 | $5.26 | 79,228 | D | M |
| 12 Feb, 2026 | John Sheldon Peters | COMMON STOCK | A | 11,845 | $11.61 | 82,073 | D | M |
| 12 Feb, 2026 | John Sheldon Peters | STOCK OPTION | D | 11,845 | $11.61 | 0 | D | M |
| 08 Jan, 2026 | John Sheldon Peters | STOCK OPTION | D | 18,457 | $5.26 | 10,000 | D | M |
| 06 Jan, 2026 | John Sheldon Peters | COMMON STOCK | D | 10,000 | $80.00 | 60,771 | D | S |
| 11 Dec, 2025 | Debra Schwartz | COMMON STOCK | D | 4,200 | $83.59 | 21,567 | D | S |
| 10 Dec, 2025 | John Sheldon Peters | COMMON STOCK | D | 3,554 | $81.00 | 70,771 | D | S |