Insider trading activities (stock purchases, sales, and option exercises) reported by insiders of Lemonade, Inc. (LMND) since 2020 are shown in Table 1 and Table 2. Table 1 shows the monthly insider trading data of Lemonade, Inc.. Table 2 shows the detailed insider transactions. This company's CIK number is 1691421.
Total stock buying since 2020: $1,477,494.
Total stock sales since 2020: $486,473,342.
Total stock option exercises since 2020: $5,299,512.
| Insider Buying | Insider Sales | Option Exercises | ||||
|---|---|---|---|---|---|---|
| Year | Shares | Value | Shares | Value | Shares | Value |
| 2025 | 0 | $0 | 3,746,597 | $121,333,319 | 176,698 | $2,977,175 |
| 2024 | 63,554 | $1,477,494 | 1,435,331 | $63,141,126 | 67,288 | $1,269,338 |
| 2023 | 0 | $0 | 14,770 | $256,664 | 15,000 | $52,800 |
| 2022 | 0 | $0 | 27,302 | $721,959 | 13,250 | $35,112 |
| 2021 | 0 | $0 | 1,193,822 | $180,827,483 | 76,750 | $859,887 |
| 2020 | 0 | $0 | 1,279,500 | $120,192,791 | 20,000 | $105,200 |
| Trading Period | Insider Buying | Insider Sales | Option Exercises | |||
|---|---|---|---|---|---|---|
| year-month | Shares | Value | Shares | Value | Shares | Value |
| 2025-08 | 0 | $0 | 48,155 | $2,824,300 | 48,155 | $683,779 |
| 2025-07 | 0 | $0 | 33,000 | $1,336,387 | 33,000 | $781,770 |
| 2025-06 | 0 | $0 | 64,205 | $2,698,650 | 60,543 | $1,313,676 |
| 2025-05 | 0 | $0 | 3,326,720 | $104,358,405 | 0 | $0 |
| 2025-04 | 0 | $0 | 14,315 | $429,532 | 20,000 | $53,000 |
| 2025-03 | 0 | $0 | 260,202 | $9,686,045 | 5,000 | $118,450 |
| 2025-01 | 0 | $0 | 0 | $0 | 10,000 | $26,500 |
| 2024-12 | 0 | $0 | 1,327,252 | $58,728,483 | 20,000 | $79,100 |
| 2024-11 | 33,554 | $1,007,444 | 97,288 | $4,227,960 | 47,288 | $1,190,238 |
| 2024-09 | 0 | $0 | 3,860 | $71,491 | 0 | $0 |
| 2024-06 | 20,000 | $304,650 | 3,374 | $54,084 | 0 | $0 |
| 2024-03 | 10,000 | $165,400 | 3,557 | $59,108 | 0 | $0 |
| 2023-12 | 0 | $0 | 2,615 | $46,285 | 0 | $0 |
| 2023-09 | 0 | $0 | 2,535 | $34,678 | 0 | $0 |
| 2023-07 | 0 | $0 | 5,000 | $100,000 | 5,000 | $26,300 |
| 2023-06 | 0 | $0 | 2,012 | $36,738 | 0 | $0 |
| 2023-03 | 0 | $0 | 2,608 | $38,963 | 0 | $0 |
| 2023-02 | 0 | $0 | 0 | $0 | 10,000 | $26,500 |
| 2022-11 | 0 | $0 | 4,265 | $106,625 | 4,265 | $11,302 |
| 2022-10 | 0 | $0 | 0 | $0 | 8,985 | $23,810 |
| 2022-03 | 0 | $0 | 12,500 | $267,087 | 0 | $0 |
| 2022-01 | 0 | $0 | 10,537 | $348,247 | 0 | $0 |
| 2021-11 | 0 | $0 | 20,500 | $1,479,495 | 500 | $1,325 |
| 2021-10 | 0 | $0 | 5,000 | $324,850 | 0 | $0 |
| Trade Date | Insider Name | Trade Type | Shares | Price ($) | Value ($) |
|---|---|---|---|---|---|
| 2025-08-13 | Eckstein Adina (Chief Operating Officer) | Sale | 5,000 | 58.00 | 290,000 |
| 2025-08-13 | Eckstein Adina (Chief Operating Officer) | Option Ex | 5,000 | 24.47 | 122,350 |
| 2025-08-13 | Peters John Sheldon (Chief Insurance Officer) | Sale | 38,155 | 60.00 | 2,289,300 |
| 2025-08-13 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 38,155 | 11.61 | 442,979 |
| 2025-08-05 | Eckstein Adina (Chief Operating Officer) | Sale | 5,000 | 49.00 | 245,000 |
| 2025-08-05 | Eckstein Adina (Chief Operating Officer) | Option Ex | 5,000 | 23.69 | 118,450 |
| 2025-07-21 | Bixby Timothy E (Chief Financial Officer) | Sale | 1,000 | 42.70 | 42,700 |
| 2025-07-21 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 1,000 | 23.69 | 23,690 |
| 2025-07-18 | Bixby Timothy E (Chief Financial Officer) | Sale | 6,000 | 42.50 | 255,000 |
| 2025-07-18 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 6,000 | 23.69 | 142,140 |
| 2025-07-14 | Bixby Timothy E (Chief Financial Officer) | Sale | 10,000 | 38.16 | 381,598 |
| 2025-07-14 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 10,000 | 23.69 | 236,900 |
| 2025-07-07 | Bixby Timothy E (Chief Financial Officer) | Sale | 11,000 | 42.39 | 466,290 |
| 2025-07-07 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 11,000 | 23.69 | 260,590 |
| 2025-06-30 | Bixby Timothy E (Chief Financial Officer) | Sale | 11,000 | 42.69 | 469,590 |
| 2025-06-30 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 11,000 | 23.69 | 260,590 |
| 2025-06-23 | Eckstein Adina (Chief Operating Officer) | Sale | 5,000 | 45.00 | 225,000 |
| 2025-06-23 | Eckstein Adina (Chief Operating Officer) | Option Ex | 5,000 | 23.69 | 118,450 |
| 2025-06-23 | Peters John Sheldon (Chief Insurance Officer) | Sale | 6,543 | 45.00 | 294,435 |
| 2025-06-23 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 6,543 | 5.26 | 34,416 |
| 2025-06-23 | Bixby Timothy E (Chief Financial Officer) | Sale | 11,000 | 43.36 | 476,960 |
| 2025-06-23 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 11,000 | 23.69 | 260,590 |
| 2025-06-16 | Bixby Timothy E (Chief Financial Officer) | Sale | 11,000 | 41.78 | 459,580 |
| 2025-06-16 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 11,000 | 23.69 | 260,590 |
| 2025-06-11 | Bixby Timothy E (Chief Financial Officer) | Sale | 6,000 | 42.50 | 255,000 |
| 2025-06-11 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 6,000 | 23.69 | 142,140 |
| 2025-06-09 | Bixby Timothy E (Chief Financial Officer) | Sale | 5,000 | 40.30 | 201,500 |
| 2025-06-09 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 5,000 | 23.69 | 118,450 |
| 2025-06-05 | Bixby Timothy E (Chief Financial Officer) | Sale | 5,000 | 37.50 | 187,500 |
| 2025-06-05 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 5,000 | 23.69 | 118,450 |
| 2025-06-03 | Prosor Maya (Chief Business Officer) | Sale | 252 | 35.25 | 8,883 |
| 2025-06-03 | Peters John Sheldon (Chief Insurance Officer) | Sale | 1,494 | 35.25 | 52,663 |
| 2025-06-03 | Bixby Timothy E (Chief Financial Officer) | Sale | 1,916 | 35.25 | 67,539 |
| 2025-05-13 | Softbank Group Capital Ltd | Sale | 387,282 | 32.91 | 12,746,612 |
| 2025-05-12 | Softbank Group Capital Ltd | Sale | 500,000 | 32.45 | 16,226,500 |
| 2025-05-09 | Softbank Group Capital Ltd | Sale | 471,960 | 31.15 | 14,701,082 |
| 2025-05-08 | Softbank Group Capital Ltd | Sale | 500,000 | 31.08 | 15,538,500 |
| 2025-05-07 | Softbank Group Capital Ltd | Sale | 316,122 | 31.39 | 9,924,017 |
| 2025-05-06 | Softbank Group Capital Ltd | Sale | 330,964 | 31.51 | 10,429,006 |
| 2025-05-05 | Softbank Group Capital Ltd | Sale | 398,215 | 30.27 | 12,054,764 |
| 2025-05-02 | Softbank Group Capital Ltd | Sale | 422,177 | 30.17 | 12,737,924 |
| 2025-04-29 | Softbank Group Capital Ltd | Sale | 13,815 | 30.01 | 414,532 |
| 2025-04-28 | Softbank Group Capital Ltd | Sale | 500 | 30.00 | 15,000 |
| 2025-04-02 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 20,000 | 2.65 | 53,000 |
| 2025-03-26 | Softbank Group Capital Ltd | Sale | 42,160 | 37.22 | 1,569,321 |
| 2025-03-24 | Softbank Group Capital Ltd | Sale | 204,575 | 37.36 | 7,643,126 |
| 2025-03-24 | Bixby Timothy E (Chief Financial Officer) | Sale | 5,000 | 37.50 | 187,500 |
| 2025-03-24 | Bixby Timothy E (Chief Financial Officer) | Option Ex | 5,000 | 23.69 | 118,450 |
| 2025-03-04 | Prosor Maya (Chief Business Officer) | Sale | 325 | 33.79 | 10,981 |
| 2025-03-04 | Peters John Sheldon (Chief Insurance Officer) | Sale | 1,899 | 33.79 | 64,167 |
| 2025-03-04 | Bixby Timothy E (Chief Financial Officer) | Sale | 6,243 | 33.79 | 210,950 |
| 2025-01-02 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 10,000 | 2.65 | 26,500 |
| 2024-12-31 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 10,000 | 2.65 | 26,500 |
| 2024-12-30 | Peters John Sheldon (Chief Insurance Officer) | Sale | 28,985 | 38.67 | 1,120,849 |
| 2024-12-30 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 10,000 | 5.26 | 52,600 |
| 2024-12-18 | Softbank Group Capital Ltd | Sale | 7,067 | 43.02 | 304,050 |
| 2024-12-17 | Softbank Group Capital Ltd | Sale | 557,291 | 43.76 | 24,385,939 |
| 2024-12-16 | Softbank Group Capital Ltd | Sale | 719,815 | 44.93 | 32,340,568 |
| 2024-12-13 | Eisenberg Michael A | Sale | 12,000 | 40.15 | 481,800 |
| 2024-12-03 | Prosor Maya (Chief Business Officer) | Sale | 304 | 45.50 | 13,832 |
| 2024-12-03 | Peters John Sheldon (Chief Insurance Officer) | Sale | 1,790 | 45.50 | 81,445 |
| 2024-11-21 | Prosor Maya (Chief Business Officer) | Sale | 30,000 | 50.00 | 1,500,000 |
| 2024-11-21 | Eckstein Adina (Chief Operating Officer) | Sale | 23,644 | 50.00 | 1,182,200 |
| 2024-11-21 | Eckstein Adina (Chief Operating Officer) | Option Ex | 23,644 | 25.17 | 595,119 |
| 2024-11-19 | Eckstein Adina (Chief Operating Officer) | Sale | 23,644 | 40.00 | 945,760 |
| 2024-11-19 | Eckstein Adina (Chief Operating Officer) | Option Ex | 23,644 | 25.17 | 595,119 |
| 2024-11-13 | Angelidis-smith Maria (Director) | Buy | 15,042 | 33.23 | 499,845 |
| 2024-11-11 | Prosor Maya (Chief Business Officer) | Sale | 20,000 | 30.00 | 600,000 |
| 2024-11-08 | Angelidis-smith Maria (Director) | Buy | 18,512 | 27.42 | 507,599 |
| 2024-09-10 | Bixby Timothy E (Chief Financial Officer) | Sale | 2,050 | 18.24 | 37,392 |
| 2024-09-04 | Prosor Maya (Chief Business Officer) | Sale | 263 | 18.84 | 4,954 |
| 2024-09-04 | Peters John Sheldon (Chief Insurance Officer) | Sale | 1,547 | 18.84 | 29,145 |
| 2024-06-14 | Bixby Timothy E (Chief Financial Officer) | Buy | 5,000 | 14.40 | 72,000 |
| 2024-06-13 | Bixby Timothy E (Chief Financial Officer) | Buy | 15,000 | 15.51 | 232,650 |
| 2024-06-04 | Prosor Maya (Chief Business Officer) | Sale | 271 | 16.03 | 4,344 |
| 2024-06-04 | Peters John Sheldon (Chief Insurance Officer) | Sale | 1,026 | 16.03 | 16,446 |
| 2024-06-04 | Bixby Timothy E (Chief Financial Officer) | Sale | 2,077 | 16.03 | 33,294 |
| 2024-03-11 | Prosor Maya (Chief Business Officer) | Sale | 290 | 17.72 | 5,138 |
| 2024-03-06 | Bixby Timothy E (Chief Financial Officer) | Buy | 10,000 | 16.54 | 165,400 |
| 2024-03-05 | Peters John Sheldon (Chief Insurance Officer) | Sale | 1,106 | 16.52 | 18,271 |
| 2024-03-05 | Bixby Timothy E (Chief Financial Officer) | Sale | 2,161 | 16.52 | 35,699 |
| 2023-12-05 | Peters John Sheldon (Chief Insurance Officer) | Sale | 869 | 17.70 | 15,381 |
| 2023-12-05 | Bixby Timothy E (Chief Financial Officer) | Sale | 1,746 | 17.70 | 30,904 |
| 2023-09-07 | Peters John Sheldon (Chief Insurance Officer) | Sale | 567 | 13.68 | 7,756 |
| 2023-09-07 | Bixby Timothy E (Chief Financial Officer) | Sale | 1,968 | 13.68 | 26,922 |
| 2023-07-17 | Peters John Sheldon (Chief Insurance Officer) | Sale | 5,000 | 20.00 | 100,000 |
| 2023-07-17 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 5,000 | 5.26 | 26,300 |
| 2023-06-05 | Peters John Sheldon (Chief Insurance Officer) | Sale | 538 | 18.26 | 9,823 |
| 2023-06-05 | Bixby Timothy E (Chief Financial Officer) | Sale | 1,474 | 18.26 | 26,915 |
| 2023-03-07 | Peters John Sheldon (Chief Insurance Officer) | Sale | 663 | 14.94 | 9,905 |
| 2023-03-07 | Bixby Timothy E (Chief Financial Officer) | Sale | 1,945 | 14.94 | 29,058 |
| 2023-02-02 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 10,000 | 2.65 | 26,500 |
| 2022-11-01 | Peters John Sheldon (Chief Insurance Officer) | Sale | 4,265 | 25.00 | 106,625 |
| 2022-11-01 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 4,265 | 2.65 | 11,302 |
| 2022-10-19 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 8,985 | 2.65 | 23,810 |
| 2022-03-17 | Eisenberg Michael A (Director) | Sale | 7,500 | 22.07 | 165,487 |
| 2022-03-16 | Eisenberg Michael A (Director) | Sale | 5,000 | 20.32 | 101,600 |
| 2022-01-19 | Peters John Sheldon (Chief Insurance Officer) | Sale | 10,537 | 33.05 | 348,247 |
| 2021-11-03 | Peters John Sheldon (Chief Insurance Officer) | Sale | 500 | 72.00 | 36,000 |
| 2021-11-03 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 500 | 2.65 | 1,325 |
| 2021-11-03 | Bixby Timothy E (Chief Financial Officer) | Sale | 15,000 | 74.93 | 1,123,995 |
| 2021-11-01 | Bixby Timothy E (Chief Financial Officer) | Sale | 5,000 | 63.90 | 319,500 |
| 2021-10-18 | Bixby Timothy E (Chief Financial Officer) | Sale | 5,000 | 64.97 | 324,850 |
| 2021-09-10 | Eisenberg Michael A (Director) | Sale | 10,000 | 77.00 | 770,000 |
| 2021-09-01 | Peters John Sheldon (Chief Insurance Officer) | Sale | 500 | 78.24 | 39,120 |
| 2021-09-01 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 500 | 2.65 | 1,325 |
| 2021-08-02 | Peters John Sheldon (Chief Insurance Officer) | Sale | 750 | 89.00 | 66,753 |
| 2021-08-02 | Peters John Sheldon (Chief Insurance Officer) | Option Ex | 750 | 2.65 | 1,987 |
| 2021-06-08 | Eisenberg Michael A (Director) | Sale | 10,000 | 103.77 | 1,037,730 |
| 2021-06-07 | Eisenberg Michael A (Director) | Sale | 10,000 | 97.19 | 971,949 |
| 2021-05-28 | Eisenberg Michael A (Director) | Sale | 20,000 | 90.27 | 1,805,400 |
| 2021-03-16 | Seidman Becker Caryn | Sale | 25,000 | 106.80 | 2,670,000 |
| 2021-03-16 | Seidman Becker Caryn | Option Ex | 25,000 | 5.26 | 131,500 |
| 2021-03-15 | Peters John Sheldon (Chief Insurance Officer) | Sale | 5,500 | 106.00 | 583,000 |
| 2021-03-01 | Espinel Jorge (CBDO) | Sale | 50,000 | 128.00 | 6,400,000 |
| 2021-03-01 | Espinel Jorge (CBDO) | Option Ex | 50,000 | 14.47 | 723,750 |
| 2021-02-16 | Peters John Sheldon (Chief Insurance Officer) | Sale | 5,500 | 165.73 | 911,515 |
| 2021-01-20 | Peters John Sheldon (Chief Insurance Officer) | Sale | 2,970 | 150.00 | 445,500 |
| 2021-01-19 | Schreiber Daniel A. (Co-Founder & CEO) | Sale | 300,000 | 159.43 | 47,829,300 |
| 2021-01-19 | Cutler Joel E | Sale | 515,572 | 159.43 | 82,198,159 |
| 2021-01-19 | Bixby Timothy E (Chief Financial Officer) | Sale | 50,000 | 159.43 | 7,971,550 |
| 2021-01-19 | Hutton George Thompson | Sale | 100,000 | 159.43 | 15,943,100 |
| 2021-01-15 | Peters John Sheldon (Chief Insurance Officer) | Sale | 62,530 | 150.01 | 9,380,062 |
| 2020-12-28 | Peters John Sheldon (Chief Insurance Officer) | Sale | 5,000 | 118.49 | 592,450 |
| 2020-12-24 | Wininger Shai (See Remarks) | Sale | 25,763 | 126.92 | 3,269,788 |
| 2020-12-23 | Wininger Shai (See Remarks) | Sale | 200,000 | 129.47 | 25,893,000 |
| 2020-12-22 | Wininger Shai (See Remarks) | Sale | 120,675 | 115.45 | 13,932,290 |
| 2020-12-21 | Wininger Shai (See Remarks) | Sale | 68,720 | 109.81 | 7,546,005 |
| 2020-12-17 | Wininger Shai (See Remarks) | Sale | 9,101 | 102.01 | 928,393 |
| 2020-12-14 | Eisenberg Michael A (Director) | Sale | 4,000 | 95.02 | 380,092 |
| 2020-12-11 | Wininger Shai (See Remarks) | Sale | 113 | 99.95 | 11,294 |
| 2020-12-11 | Eisenberg Michael A (Director) | Sale | 6,000 | 97.38 | 584,298 |
| 2020-12-10 | Wininger Shai (See Remarks) | Sale | 111,222 | 105.47 | 11,730,806 |
| 2020-12-10 | Eisenberg Michael A (Director) | Sale | 5,000 | 103.71 | 518,549 |
| 2020-12-08 | Schreiber Daniel A. (Co-Founder & CEO) | Sale | 218,750 | 92.47 | 20,228,250 |
| 2020-12-08 | Eisenberg Michael A (Director) | Sale | 15,834 | 93.64 | 1,482,695 |
| 2020-12-07 | Wininger Shai (See Remarks) | Sale | 906 | 99.52 | 90,165 |
| 2020-12-07 | Eisenberg Michael A (Director) | Sale | 4,166 | 91.25 | 380,147 |
| 2020-12-04 | Eisenberg Michael A (Director) | Sale | 6,500 | 81.58 | 530,270 |
| 2020-12-03 | Peters John Sheldon (Chief Insurance Officer) | Sale | 19,200 | 75.00 | 1,440,000 |
| 2020-12-03 | Schreiber Daniel A. (Co-Founder & CEO) | Sale | 111,800 | 76.72 | 8,577,519 |
| 2020-12-03 | Eisenberg Michael A (Director) | Sale | 8,500 | 80.08 | 680,705 |
| 2020-12-03 | Bixby Timothy E (Chief Financial Officer) | Sale | 19,900 | 74.00 | 1,472,600 |
| 2020-12-02 | Schreiber Daniel A. (Co-Founder & CEO) | Sale | 300 | 66.01 | 19,802 |
| 2020-12-01 | Peters John Sheldon (Chief Insurance Officer) | Sale | 28,800 | 66.47 | 1,914,479 |
| 2020-12-01 | Schreiber Daniel A. (Co-Founder & CEO) | Sale | 56,650 | 66.48 | 3,766,375 |
| 2020-12-01 | Bixby Timothy E (Chief Financial Officer) | Sale | 20,100 | 66.53 | 1,337,273 |
| 2020-11-27 | Eisenberg Michael A (Director) | Sale | 7,900 | 71.61 | 565,719 |
| 2020-11-25 | Eisenberg Michael A (Director) | Sale | 100 | 72.20 | 7,220 |
| 2020-11-24 | Bixby Timothy E (Chief Financial Officer) | Sale | 10,000 | 69.04 | 690,370 |
| 2020-11-17 | Schreiber Daniel A. (Co-Founder & CEO) | Sale | 34,700 | 64.54 | 2,239,642 |
| 2020-11-17 | Bixby Timothy E (Chief Financial Officer) | Sale | 20,000 | 64.24 | 1,284,880 |
| 2020-11-13 | Peters John Sheldon (Chief Insurance Officer) | Sale | 42,000 | 58.11 | 2,440,536 |
| 2020-11-13 | Espinel Jorge (CBDO) | Sale | 20,000 | 58.09 | 1,161,740 |
| 2020-11-13 | Espinel Jorge (CBDO) | Option Ex | 20,000 | 5.26 | 105,200 |
| 2020-11-12 | Schreiber Daniel A. (Co-Founder & CEO) | Sale | 77,800 | 57.78 | 4,495,439 |
Insider trading activities including stock purchases, stock sales, and option exercises of LMND listed in the above tables cannot be completely guaranteed as to their accuracy. For more insider trading information of Lemonade, Inc. (symbol LMND, CIK number 1691421) see the Securities and Exchange Commission (SEC) website.