LMND insider buying and SEC filings, explained
Lemonade, Inc. · CIK 1691421
Tracked: Forms 3/4/5, 8-K, NT · All filings on sec.gov
Insider activity in the last 12 months
Bought
$485K
Insiders who bought
1
Sold (not marked 10b5-1)
$4.2M
Planned sales (10b5-1)
$33.6M
Insider purchases and sales, last 12 months
| Traded | Type | What was filed | Source |
|---|---|---|---|
| Sep 3, 2026 | Sale | Maya Prosor (Chief Business Officer) sold 1,040 shares at $54.63 ($57K). Holdings down 1% to 186,533 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Sep 8, 2026 |
| Sep 3–4, 2026 | Planned (10b5-1) | John Sheldon Peters (Chief Insurance Officer) sold 3,108 shares between Sep 3 and Sep 4 at about $54.50 ($169K), marked as a 10b5-1 plan trade. Holdings down 4% to 73,834 shares. | SEC filing Filed Sep 8, 2026 |
| Sep 3, 2026 | Sale | Timothy E. Bixby (CFO) sold 1,893 shares at $54.63 ($103K). Holdings down 1% to 172,370 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Sep 8, 2026 |
| Aug 13, 2026 | Sale | John Sheldon Peters (Chief Insurance Officer) sold 11,000 shares at about $52.55 ($578K). Holdings down 13% to 76,942 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Aug 17, 2026 |
| Jul 7, 2026 | Planned (10b5-1) | Timothy E. Bixby (CFO) sold 73,000 shares at about $79.18 ($5.8M), marked as a 10b5-1 plan trade. Holdings down 30% to 174,263 shares. | SEC filing Filed Jul 9, 2026 |
| Jul 6, 2026 | Planned (10b5-1) | John Sheldon Peters (Chief Insurance Officer) sold 3,444 shares at $79.00 ($272K), marked as a 10b5-1 plan trade. Holdings down 4% to 77,942 shares. | SEC filing Filed Jul 8, 2026 |
| Jun 3, 2026 | Sale | Maya Prosor (Chief Business Officer) sold 1,220 shares at $53.17 ($65K). Holdings down 1% to 187,573 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Jun 5, 2026 |
| Jun 3–4, 2026 | Planned (10b5-1) | John Sheldon Peters (Chief Insurance Officer) sold 5,343 shares between Jun 3 and Jun 4 at about $53.01 ($283K), marked as a 10b5-1 plan trade. Holdings down 6% to 81,386 shares. | SEC filing Filed Jun 5, 2026 |
| Jun 3, 2026 | Sale | Timothy E. Bixby (CFO) sold 2,227 shares at $53.17 ($118K). Holdings down 1% to 247,263 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Jun 5, 2026 |
| Mar 10, 2026 | Open-market purchase Amended filing | Maria Angelidis-Smith (Director) bought 8,740 shares directly and indirectly (by trust) at about $55.55 ($485K) in an open-market purchase. Direct holdings up 29% to 14,896 shares. Not marked as a 10b5-1 plan trade. This amends a filing from Mar 12. | SEC filing Filed Mar 30, 2026 |
| Mar 3, 2026 | Sale | Maya Prosor (Chief Business Officer) sold 223 shares at $50.12 ($11K). Holdings down 3% to 7,404 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Mar 5, 2026 |
| Mar 3–4, 2026 | Planned (10b5-1) | John Sheldon Peters (Chief Insurance Officer) sold 5,344 shares between Mar 3 and Mar 4 at about $51.71 ($276K), marked as a 10b5-1 plan trade. Holdings down 7% to 76,729 shares. | SEC filing Filed Mar 5, 2026 |
| Mar 3, 2026 | Sale | Timothy E. Bixby (CFO) sold 2,135 shares at $50.12 ($107K). Holdings down 1% to 249,490 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Mar 5, 2026 |
| Jan 23, 2026 | Planned (10b5-1) | Daniel A. Schreiber (CEO and Director) sold 9,108 shares indirectly at about $99.04 ($902K), marked as a 10b5-1 plan trade. Indirect holdings down 1% to 1,514,426 shares. | SEC filing Filed Feb 4, 2026 |
| Jan 22, 2026 | Planned (10b5-1) | John Sheldon Peters (Chief Insurance Officer) sold 9,000 shares at $90.00 ($810K), marked as a 10b5-1 plan trade. Holdings down 11% to 70,228 shares. | SEC filing Filed Jan 23, 2026 |
| Jan 22, 2026 | Planned (10b5-1) | Daniel A. Schreiber (CEO and Director) sold 126,625 shares indirectly at about $94.74 ($12.0M), marked as a 10b5-1 plan trade. Indirect holdings down 8% to 1,523,534 shares. | SEC filing Filed Jan 23, 2026 |
| Jan 6, 2026 | Planned (10b5-1) | John Sheldon Peters (Chief Insurance Officer) sold 10,000 shares at $80.00 ($800K), marked as a 10b5-1 plan trade. Holdings down 14% to 60,771 shares. | SEC filing Filed Jan 8, 2026 |
| Dec 11, 2025 | Sale | Debra Schwartz (Director) sold 4,200 shares at about $83.59 ($351K). Holdings down 16% to 21,567 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Dec 15, 2025 |
| Dec 11, 2025 | Planned (10b5-1) | Adina Eckstein (President / COO) sold 7,919 shares at about $84.15 ($666K), marked as a 10b5-1 plan trade. Holdings down 4% to 188,391 shares. | SEC filing Filed Dec 15, 2025 |
| Dec 10, 2025 | Planned (10b5-1) | Adina Eckstein (President / COO) sold 7,919 shares at about $81.15 ($643K), marked as a 10b5-1 plan trade. Holdings down 4% to 196,310 shares. | SEC filing Filed Dec 11, 2025 |
| Dec 10, 2025 | Sale | John Sheldon Peters (Chief Insurance Officer) sold 3,554 shares at $81.00 ($288K). Holdings down 5% to 70,771 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Dec 11, 2025 |
| Dec 8–9, 2025 | Planned (10b5-1) | Adina Eckstein (President / COO) sold 70,794 shares between Dec 8, 2025 and Dec 9, 2025 at about $78.21 ($5.5M), marked as a 10b5-1 plan trade. Holdings down 26% to 204,229 shares. | SEC filing Filed Dec 10, 2025 |
| Dec 2, 2025 | Sale | Maya Prosor (Chief Business Officer) sold 198 shares at $72.74 ($14K). Holdings down 3% to 7,627 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Dec 4, 2025 |
| Dec 2–3, 2025 | Planned (10b5-1) | John Sheldon Peters (Chief Insurance Officer) sold 5,344 shares between Dec 2, 2025 and Dec 3, 2025 at about $72.56 ($388K), marked as a 10b5-1 plan trade. Holdings down 7% to 74,325 shares. | SEC filing Filed Dec 4, 2025 |
| Dec 2, 2025 | Sale | Timothy E. Bixby (CFO) sold 2,862 shares at $72.74 ($208K). Holdings down 1% to 251,625 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Dec 4, 2025 |
| Nov 20–24, 2025 | Planned (10b5-1) | John Sheldon Peters (Chief Insurance Officer) sold 22,728 shares between Nov 20, 2025 and Nov 24, 2025 at about $72.85 ($1.7M), marked as a 10b5-1 plan trade. Holdings down 22% to 79,669 shares. | SEC filing Filed Nov 24, 2025 |
| Nov 7–10, 2025 | Planned (10b5-1) | Adina Eckstein (President / COO) sold 45,988 shares between Nov 7, 2025 and Nov 10, 2025 at about $73.67 ($3.4M), marked as a 10b5-1 plan trade. Holdings down 17% to 227,987 shares. | SEC filing Filed Nov 12, 2025 |
| Nov 11, 2025 | Sale | Timothy E. Bixby (CFO) sold 30,000 shares indirectly (by trust) at $75.51 ($2.3M). Holdings by trust down 100% to 0 shares. Not marked as a 10b5-1 plan trade. | SEC filing Filed Nov 12, 2025 |
19 routine transactions (such as grants, option exercises or tax withholding) are not listed.
Cluster buys
No cluster buys in the last 12 months.
Red flags
No red flags in the last 12 months.
Key events
No key events in the last 12 months.
8-K filings, last 12 months
No 8-K filings in the last 12 months.
Red flags are objective triggers only: the item or form filed, never an opinion.
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