13 insiders reported 137 Form 4 transactions for Lemonade, Inc. (LMND) over the past 18 months (most recent 2026-08-17). Recent activity: Peters John Sheldon (Chief Insurance Officer) Sell 11,000 shares, Peters John Sheldon (Chief Insurance Officer) Buy 10,000 shares, BIXBY TIMOTHY E (Chief Financial Officer) Sell 73,000 shares, Peters John Sheldon (Chief Insurance Officer) Sell 3,444 shares, Eisenberg Michael A (Director) Sell 5,000 shares. Source: SEC Form 4.
| Date | Insider | Title | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-08-17 | Peters John Sheldon | Chief Insurance Officer | Sell | 11,000 | $578,050 |
| 2026-07-29 | Peters John Sheldon | Chief Insurance Officer | Buy | 10,000 | $0 |
| 2026-07-09 | BIXBY TIMOTHY E | Chief Financial Officer | Sell | 73,000 | $5.8M |
| 2026-07-08 | Peters John Sheldon | Chief Insurance Officer | Sell | 3,444 | $272,076 |
| 2026-06-12 | Eisenberg Michael A | Director | Sell | 5,000 | $0 |
| 2026-06-05 | Angelidis-Smith Maria | Director | Buy | 2,848 | $0 |
| 2026-06-05 | Peters John Sheldon | Chief Insurance Officer | Sell | 1,735 | $92,250 |
| 2026-06-05 | Schwartz Debra | Director | Buy | 2,848 | $0 |
| 2026-06-05 | Haj-Yehia Samer | Director | Buy | 2,848 | $0 |
| 2026-06-05 | Prosor Maya | Chief Business Officer | Sell | 1,220 | $64,867 |
| 2026-06-05 | BIXBY TIMOTHY E | Chief Financial Officer | Sell | 2,227 | $118,410 |
| 2026-06-05 | Seeley Geoff | Director | Buy | 2,848 | $0 |
| 2026-06-05 | Peters John Sheldon | Chief Insurance Officer | Sell | 3,608 | $191,008 |
| 2026-06-05 | Ratanchandani Prashant | Director | Buy | 2,848 | $0 |
| 2026-03-30 | Angelidis-Smith Maria | Director | Buy | 3,350 | $185,255 |
| 2026-03-30 | Angelidis-Smith Maria | Director | Buy | 5,390 | $300,223 |
| 2026-03-20 | Wininger Shai | President | Buy | 820,000 | $0 |
| 2026-03-20 | Wininger Shai | President | Buy | 180,000 | $0 |
| 2026-03-20 | Schreiber Daniel A. | Chief Executive Officer | Buy | 820,000 | $0 |
| 2026-03-20 | Schreiber Daniel A. | Chief Executive Officer | Buy | 180,000 | $0 |
| 2026-03-12 | Angelidis-Smith Maria | Director | Buy | 3,350 | $185,255 |
| 2026-03-12 | Angelidis-Smith Maria | Director | Buy | 5,390 | $300,223 |
| 2026-03-10 | Prosor Maya | Chief Business Officer | Buy | 181,389 | $0 |
| 2026-03-10 | Eckstein Adina | Chief Operating Officer | Buy | 145,112 | $0 |
| 2026-03-05 | Peters John Sheldon | Chief Insurance Officer | Sell | 1,773 | $88,863 |
Source: SEC Form 4 filings · as of 2026-08-17