LMND · Insider Trading
Lemonade, Inc.
Every open-market purchase and sale reported by LMND officers, directors and 10%+ beneficial owners on SEC Form 4, which must be filed within two business days of the transaction. Sales often reflect scheduled 10b5-1 plans or tax withholding rather than a directional view, so read counts alongside the size and the filer.
| Filed | Insider | Role | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-09-08 | Timothy E Bixby | Chief Financial Officer | Sell | −1,893 | −$103.41K |
| 2026-09-08 | Maya Prosor | Chief Business Officer | Sell | −1,040 | −$56.82K |
| 2026-09-08 | John Sheldon Peters | Chief Insurance Officer | Sell | −3,108 | −$169.39K |
| 2026-09-04 | Shai Wininger | President | G | −1,876 | — |
| 2026-08-17 | John Sheldon Peters | Chief Insurance Officer | Sell | −11,000 | −$578.05K |
| 2026-07-29 | John Sheldon Peters | Chief Insurance Officer | A | +10,000 | — |
| 2026-07-09 | Timothy E Bixby | Chief Financial Officer | Sell | −73,000 | −$5.78M |
| 2026-07-08 | John Sheldon Peters | Chief Insurance Officer | Sell | −3,444 | −$272.08K |
| 2026-06-12 | Michael A Eisenberg | Director | G | −5,000 | — |
| 2026-06-05 | Geoff Seeley | Director | A | +2,848 | — |
| 2026-06-05 | Debra Schwartz | Director | A | +2,848 | — |
| 2026-06-05 | John Sheldon Peters | Chief Insurance Officer | Sell | −5,343 | −$283.26K |
| 2026-06-05 | Timothy E Bixby | Chief Financial Officer | Sell | −2,227 | −$118.41K |
| 2026-06-05 | Samer Haj-Yehia | Director | A | +2,848 | — |
| 2026-06-05 | Prashant Ratanchandani | Director | A | +2,848 | — |
| 2026-06-05 | Maya Prosor | Chief Business Officer | Sell | −1,220 | −$64.87K |
| 2026-06-05 | Maria Angelidis-Smith | Director | A | +2,848 | — |
| 2026-03-30 | Maria Angelidis-Smith | Director | Buy | +8,740 | +$485.48K |
| 2026-03-20 | Shai Wininger | President | A | +1,000,000 | — |
| 2026-03-20 | Daniel A. Schreiber | Chief Executive Officer | A | +1,000,000 | — |
| 2026-03-12 | Maria Angelidis-Smith | Director | A | +8,740 | +$485.48K |
| 2026-03-10 | Adina Eckstein | Chief Operating Officer | A | +145,112 | — |
| 2026-03-10 | Maya Prosor | Chief Business Officer | A | +181,389 | — |
| 2026-03-05 | Timothy E Bixby | Chief Financial Officer | Sell | −2,135 | −$107.01K |
| 2026-03-05 | John Sheldon Peters | Chief Insurance Officer | Sell | −5,344 | −$276.34K |
| 2026-03-05 | Maya Prosor | Chief Business Officer | Sell | −223 | −$11.18K |
| 2026-02-17 | John Sheldon Peters | Chief Insurance Officer | M | +11,845 | +$137.52K |
| 2023-03-09 | John Sheldon Peters | Chief Insurance Officer | Sell | −663 | −$9.91K |
| 2023-03-09 | Timothy E Bixby | Chief Financial Officer | Sell | −1,945 | −$29.06K |
| 2023-02-09 | Adina Eckstein | Chief Operating Officer | A | +75,000 | — |
| 2023-02-09 | John Sheldon Peters | Chief Insurance Officer | A | +30,000 | — |
| 2023-02-09 | Timothy E Bixby | Chief Financial Officer | A | +67,000 | — |
| 2023-02-06 | John Sheldon Peters | Chief Insurance Officer | M | +10,000 | +$26.50K |
| 2022-11-03 | John Sheldon Peters | Chief Insurance Officer | MIXED | — | −$95.32K |
| 2022-10-21 | John Sheldon Peters | Chief Insurance Officer | M | +8,985 | +$23.81K |
| 2022-08-22 | Mwashuma Kamata Nyatta | Director | A | +6,158 | — |
| 2022-08-17 | Daniel A. Schreiber | Co-Chief Executive Officer | A | +500,000 deriv. | — |
| 2022-08-17 | Shai Wininger | Co-Chief Executive Officer | A | +500,000 deriv. | — |
| 2022-06-10 | Silvija Martincevic | Director | A | +7,285 | +$150.00K |
| 2022-06-10 | Irina Novoselsky | Director | A | +7,285 | +$150.00K |
| 2022-04-07 | John Sheldon Peters | Chief Insurance Officer | A | +25,000 deriv. | — |
| 2022-04-07 | Timothy E Bixby | Chief Financial Officer | A | +212,500 deriv. | — |
| 2022-04-07 | Adina Eckstein | Chief Operating Officer | A | +56,600 deriv. | — |
| 2022-03-18 | Michael A Eisenberg | Director | Sell | −12,500 | −$263.66K |
| 2022-01-21 | John Sheldon Peters | Chief Insurance Officer | Sell | −10,537 | −$348.25K |
| 2021-12-08 | John Sheldon Peters | Chief Insurance Officer | A | +25,000 deriv. | — |
| 2021-12-08 | Adina Eckstein | Chief Operating Officer | A | +35,300 deriv. | — |
| 2021-12-08 | Jorge Espinel | CBDO | A | +50,000 deriv. | — |
| 2021-11-05 | John Sheldon Peters | Chief Insurance Officer | MIXED | — | −$34.67K |
| 2021-11-03 | Timothy E Bixby | Chief Financial Officer | Sell | −20,000 | −$1.44M |
| Insider | Role | Shares Held | Value |
|---|---|---|---|
| Shai Wininger | President | 16,400,257 | $724.73M |
| Daniel A. Schreiber | Chief Executive Officer | 2,538,753 | $112.19M |
| Michael A Eisenberg | Director | 1,174,196 | $51.89M |
| Adina Eckstein | Chief Operating Officer | 333,503 | $14.74M |
| Maya Prosor | Chief Business Officer | 215,819 | $9.54M |
| Timothy E Bixby | Chief Financial Officer | 172,370 | $7.62M |
| John Sheldon Peters | Chief Insurance Officer | 73,834 | $3.26M |
| Maria Angelidis-Smith | Director | 56,688 | $2.51M |
| Samer Haj-Yehia | Director | 27,187 | $1.20M |
| Debra Schwartz | Director | 24,415 | $1.08M |
| Prashant Ratanchandani | Director | 6,185 | $273.32K |
| Geoff Seeley | Director | 5,967 | $263.68K |
Form 4 reports a change in beneficial ownership by an officer, director or 10%+ holder, and must be filed within two business days of the transaction — so this is close to real time, unlike the 45-day-lagged 13F institutional data.
Transaction codes matter more than the raw buy/sell count. Code P is an open-market purchase — an insider choosing to buy with their own money, which is the signal most research treats as informative. Code S is a sale, but sales are frequently pre-scheduled under a 10b5-1 plan or cover tax withholding on vesting equity, so a run of sales often says nothing directional. Codes A and M are grants and option exercises rather than open-market decisions.
Full filing history and per-insider positions are on the LMND quote page; the site-wide leaderboard is on the insider transactions hub.
Market data may be delayed, incomplete, or inaccurate. Not a recommendation to buy, sell, or hold any security. Verify quotes with your broker before trading. See Terms §17.