Lemonade (NYSE: LMND) insider transactions
In the twelve months to 10 November 2026, executives and directors of Lemonade reported 34 open-market sales of 420,228 shares ($34.3m) and 0 open-market purchases, by 6 people, according to the Form 4 filings they submitted to the SEC.
Latest transactions
| Date | Insider | Role | Transaction | Shares | Price | Held after | Filing |
|---|---|---|---|---|---|---|---|
| 4 September 2026 | Peters John Sheldon | Chief Insurance Officer | Open-market sale, 10b5-1 plan | −2,249 | $54.45 | 73,834 | Form 4 |
| 3 September 2026 | Bixby Timothy E | Chief Financial Officer | Open-market sale | −1,893 | $54.63 | 172,370 | Form 4 |
| 3 September 2026 | Peters John Sheldon | Chief Insurance Officer | Open-market sale, 10b5-1 plan | −859 | $54.63 | 76,083 | Form 4 |
| 3 September 2026 | Prosor Maya | Chief Business Officer | Open-market sale | −1,040 | $54.63 | 186,533 | Form 4 |
| 2 September 2026 | Wininger Shai | President | Gift | −1,876 | — | 4,416,873 | Form 4 |
| 13 August 2026 | Peters John Sheldon | Chief Insurance Officer | Open-market sale | −11,000 | $52.55 | 76,942 | Form 4 |
| 27 July 2026 | Peters John Sheldon | Chief Insurance Officer | Grant or award | +10,000 | — | 87,942 | Form 4 |
| 7 July 2026 | Bixby Timothy E | Chief Financial Officer | Open-market sale, 10b5-1 plan | −73,000 | $79.18 | 174,263 | Form 4 |
| 6 July 2026 | Peters John Sheldon | Chief Insurance Officer | Open-market sale | −3,444 | $79.00 | 77,942 | Form 4 |
| 10 June 2026 | Eisenberg Michael A | Director | Gift | −5,000 | — | 195,452 | Form 4 |
| 4 June 2026 | Peters John Sheldon | Chief Insurance Officer | Open-market sale, 10b5-1 plan | −3,608 | $52.94 | 81,386 | Form 4 |
| 3 June 2026 | Bixby Timothy E | Chief Financial Officer | Open-market sale | −2,227 | $53.17 | 247,263 | Form 4 |
| 3 June 2026 | Peters John Sheldon | Chief Insurance Officer | Open-market sale, 10b5-1 plan | −1,735 | $53.17 | 84,994 | Form 4 |
| 3 June 2026 | Schwartz Debra | Director | Grant or award | +2,848 | — | 24,415 | Form 4 |
| 3 June 2026 | Haj-Yehia Samer | Director | Grant or award | +2,848 | — | 27,187 | Form 4 |
| 3 June 2026 | Prosor Maya | Chief Business Officer | Open-market sale | −1,220 | $53.17 | 187,573 | Form 4 |
| 3 June 2026 | Angelidis-Smith Maria | Director | Grant or award | +2,848 | — | 17,744 | Form 4 |
| 3 June 2026 | Seeley Geoff | Director | Grant or award | +2,848 | — | 5,967 | Form 4 |
| 3 June 2026 | Ratanchandani Prashant | Director | Grant or award | +2,848 | — | 6,185 | Form 4 |
| 18 March 2026 | Wininger Shai | President | Grant or award | +820,000 | — | 4,238,749 | Form 4 |
Names appear as in the filing, surname first. A dash in the price column means the filing reports none, as in grants and gifts.
How to read the table
Only open-market purchases and sales are trades the insider chose to make at the market price, and they are the ones counted in the summary above. Grants, option exercises and shares withheld for tax come from pay plans. A sale marked as a 10b5-1 plan was scheduled in advance under a written plan.
Where each row comes from
From the Form 4 that each executive, director or large shareholder must file with the SEC within two business days of a transaction, read up to 10 November 2026. Each row links to its filing on EDGAR. Only transactions in shares are listed, not derivatives, and amended filings are left out. The accounts of the company are on the Lemonade page; the method, in data sources.
Information prepared from the Form 4 filings submitted to the SEC, for information purposes only. It is not financial advice or a recommendation to buy or sell. Updated on 12 November 2026.