Lemonade, Inc. — Insider Transactions
Form 4 filings by directors, officers, and 10%+ shareholders
SEC rules require corporate insiders — including directors, executive officers, and any shareholder owning more than 10% of a company's shares — to report changes in their ownership within two business days of a transaction. These disclosures are filed as Form 4. Open-market purchases (code P) are generally considered the most meaningful signal, as insiders are spending their own money.
| Insider | Title | Type | Shares | Price | Value | Owns After | Date |
|---|---|---|---|---|---|---|---|
| Eckstein Adina | Chief Operating Officer | Sale | 7,919 | $84.15 | $666,384 | 188,391 | Dec 11, 2025 |
| Schwartz Debra | — | Sale | 4,200 | $83.59 | $351,078 | 21,567 | Dec 11, 2025 |
| Eckstein Adina | Chief Operating Officer | Sale | 7,919 | $81.15 | $642,627 | 196,310 | Dec 10, 2025 |
| Peters John Sheldon | Chief Insurance Officer | Sale | 3,554 | $81.00 | $287,874 | 70,771 | Dec 10, 2025 |
| Eckstein Adina | Chief Operating Officer | Option Exercise | 16,250 | $24.47 | $397,638 | 244,237 | Dec 9, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Sale | 2,862 | $72.74 | $208,182 | 251,625 | Dec 2, 2025 |
| Prosor Maya | Chief Business Officer | Sale | 198 | $72.74 | $14,403 | 7,627 | Dec 2, 2025 |
| Peters John Sheldon | Chief Insurance Officer | Sale | 2,667 | $72.37 | $193,011 | 74,325 | Dec 2, 2025 |
| Peters John Sheldon | Chief Insurance Officer | Sale | 18,930 | $72.77 | $1,377,536 | 83,467 | Nov 24, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Gift | 6,000 | — | — | 254,487 | Nov 11, 2025 |
| Schreiber Daniel A. | Chief Executive Officer | Gift | 35,000 | — | — | 24,327 | Nov 11, 2025 |
| Eckstein Adina | Chief Operating Officer | Sale | 20,000 | $72.04 | $1,440,800 | 227,987 | Nov 7, 2025 |
| Ratanchandani Prashant | — | Award / Grant | 3,337 | — | — | 3,337 | Oct 16, 2025 |
| Seeley Geoff | — | Award / Grant | 3,119 | — | — | 3,119 | Oct 7, 2025 |
| Eisenberg Michael A | — | Gift | 4,000 | — | — | 200,452 | Sep 12, 2025 |
| Prosor Maya | Chief Business Officer | Sale | 282 | $50.34 | $14,196 | 7,825 | Sep 3, 2025 |
| Peters John Sheldon | Chief Insurance Officer | Sale | 2,718 | $50.34 | $136,824 | 102,397 | Sep 3, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Sale | 2,906 | $50.34 | $146,288 | 260,487 | Sep 3, 2025 |
| Eckstein Adina | Chief Operating Officer | Award / Grant | 38,334 | — | — | 227,987 | Aug 21, 2025 |
| Eckstein Adina | Chief Operating Officer | Option Exercise | 5,000 | $24.47 | $122,350 | 189,653 | Aug 13, 2025 |
| Peters John Sheldon | Chief Insurance Officer | Option Exercise | 38,155 | $11.61 | $442,980 | 143,270 | Aug 12, 2025 |
| Eckstein Adina | Chief Operating Officer | Sale | — | $53.00 | — | 189,653 | Aug 11, 2025 |
| Eckstein Adina | Chief Operating Officer | Option Exercise | 3,750 | $23.69 | $88,838 | 194,653 | Aug 5, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Option Exercise | 1,000 | $23.69 | $23,690 | 264,393 | Jul 18, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Option Exercise | 5,000 | $23.69 | $118,450 | 268,393 | Jul 14, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Option Exercise | 11,000 | $23.69 | $260,590 | 274,393 | Jul 7, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Option Exercise | 11,000 | $23.69 | $260,590 | 274,393 | Jun 30, 2025 |
| Eckstein Adina | Chief Operating Officer | Option Exercise | 5,000 | $23.69 | $118,450 | 194,653 | Jun 23, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Sale | 11,000 | $43.36 | $476,960 | 263,393 | Jun 23, 2025 |
| Peters John Sheldon | Chief Insurance Officer | Option Exercise | 6,543 | $5.26 | $34,416 | 112,658 | Jun 23, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Option Exercise | 11,000 | $23.69 | $260,590 | 274,393 | Jun 16, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Option Exercise | 6,000 | $23.69 | $142,140 | 269,393 | Jun 11, 2025 |
| Haj-Yehia Samer | — | Award / Grant | 4,184 | — | — | 24,339 | Jun 10, 2025 |
| Schwartz Debra | — | Award / Grant | 4,184 | — | — | 25,767 | Jun 10, 2025 |
| Angelidis-Smith Maria | — | Award / Grant | 4,184 | — | — | 11,546 | Jun 10, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Sale | 5,000 | $40.30 | $201,500 | 263,393 | Jun 9, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Sale | 5,000 | $37.50 | $187,500 | 263,393 | Jun 5, 2025 |
| Peters John Sheldon | Chief Insurance Officer | Sale | 1,494 | $35.25 | $52,664 | 106,115 | Jun 3, 2025 |
| BIXBY TIMOTHY E | Chief Financial Officer | Sale | 1,916 | $35.25 | $67,539 | 263,393 | Jun 3, 2025 |
| Prosor Maya | Chief Business Officer | Sale | 252 | $35.25 | $8,883 | 8,107 | Jun 3, 2025 |
| SoftBank Group Capital Ltd | — | Sale | 77,092 | $33.03 | $2,546,349 | 7,111,441 | May 12, 2025 |
| SoftBank Group Capital Ltd | — | Sale | 471,960 | $31.15 | $14,701,554 | 7,998,723 | May 8, 2025 |
| SoftBank Group Capital Ltd | — | Sale | 152,910 | $31.51 | $4,818,194 | 8,987,512 | May 7, 2025 |
| SoftBank Group Capital Ltd | — | Sale | 61,928 | $30.80 | $1,907,382 | 9,555,841 | May 5, 2025 |
| SoftBank Group Capital Ltd | — | Sale | 422,177 | $30.17 | $12,737,080 | 10,015,984 | May 2, 2025 |
| SoftBank Group Capital Ltd | — | Sale | 13,815 | $30.01 | $414,588 | 10,438,161 | Apr 29, 2025 |
| SoftBank Group Capital Ltd | — | Sale | 500 | $30.00 | $15,000 | 10,451,976 | Apr 28, 2025 |
| Peters John Sheldon | Chief Insurance Officer | Option Exercise | 20,000 | $2.65 | $53,000 | 107,609 | Apr 2, 2025 |
| SoftBank Group Capital Ltd | — | Sale | 42,160 | $37.22 | $1,569,195 | 10,452,476 | Mar 26, 2025 |
| SoftBank Group Capital Ltd | — | Sale | 112,714 | $37.15 | $4,187,325 | 10,501,365 | Mar 24, 2025 |