Dudediligence.

Lemonade, Inc

LMNDNYSE · Fire, Marine & Casualty Insurance
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Last 12 months

Sales planned on beside the trades reported on , and whether each names a .

Planned ·

$38.7M

33 notices · 474,483 sh

Oct 2025 to Oct 2026

Reported ·

$30.8M

30 sales · 2 buys · $485,478 bought

Oct 2025 to Jun 2026

The two figures cover different periods.

21 of 30 reported sales carry the 10b5-1 box. Together they are 0.48% of the shares on issue.

PLANNED · FORM 144Oct 2025 to Oct 2026REPORTED · FORM 4Oct 2025 to Jun 2026N2025DJ2026FMAMJJASO2026-09-04: Peters John Sheldon, Form 1442026-09-03: Peters John Sheldon, Form 1442026-09-03: BIXBY TIMOTHY E, Form 1442026-09-03: Prosor Maya, Form 1442026-08-13: Peters John Sheldon, Form 1442026-07-07: BIXBY TIMOTHY E, Form 1442026-07-06: Peters John Sheldon, Form 1442026-06-04: Peters John Sheldon, Form 1442026-06-03: Peters John Sheldon, Form 1442026-06-03: Prosor Maya, Form 1442026-06-03: BIXBY TIMOTHY E, Form 1442026-03-04: Peters John Sheldon, Form 1442026-03-03: BIXBY TIMOTHY E, Form 1442026-03-03: Prosor Maya, Form 1442026-03-03: Peters John Sheldon, Form 1442026-01-22: Peters John Sheldon, Form 1442026-01-22: Daniel Schreiber, Form 1442026-01-06: Peters John Sheldon, Form 1442025-12-11: Eckstein Adina, Form 1442025-12-11: Schwartz Debra, Form 1442025-12-10: Eckstein Adina, Form 1442025-12-10: Peters John Sheldon, Form 1442025-12-08: Eckstein Adina, Form 1442025-12-03: Peters John Sheldon, Form 1442025-12-02: BIXBY TIMOTHY E, Form 1442025-12-02: Peters John Sheldon, Form 1442025-12-02: Prosor Maya, Form 1442025-11-24: Peters John Sheldon, Form 1442025-11-20: Peters John Sheldon, Form 1442025-11-11: BIXBY TIMOTHY E, Form 1442025-11-10: Eckstein Adina, Form 1442025-11-07: Eckstein Adina, Form 1442025-11-07: Eckstein Adina, Form 1442025-11-07: Eckstein Adina, sold2025-11-11: BIXBY TIMOTHY E, sold2025-11-20: Peters John Sheldon, sold2025-12-02: BIXBY TIMOTHY E, sold2025-12-02: Peters John Sheldon, sold2025-12-02: Prosor Maya, sold2025-12-08: Eckstein Adina, sold2025-12-10: Peters John Sheldon, sold2025-12-10: Eckstein Adina, sold2025-12-11: Eckstein Adina, sold2025-12-11: Schwartz Debra, sold2026-01-06: Peters John Sheldon, sold2026-01-22: Schreiber Daniel A., sold2026-01-22: Peters John Sheldon, sold2026-01-23: Schreiber Daniel A., sold2026-03-03: BIXBY TIMOTHY E, sold2026-03-03: Peters John Sheldon, sold2026-03-03: Prosor Maya, sold2026-03-10: Angelidis-Smith Maria, bought2026-06-03: BIXBY TIMOTHY E, sold2026-06-03: Peters John Sheldon, sold2026-06-03: Prosor Maya, sold
under a no plan named▼ sale▲ buysize is dollars

Form 144 notices, newest first

2026-09-04Peters John Sheldon, Chief Insurance Officer$122,458
2,249 shplan 2026-03-12Form 4s on file end Jun 23144 ↗
2026-09-03Peters John Sheldon, Chief Insurance Officer$46,928
859 shplan 2026-03-12Form 4s on file end Jun 23144 ↗
2026-09-03BIXBY TIMOTHY E, Chief Financial Officer$103,416
1,893 shplan 2026-03-12Form 4s on file end Jun 23144 ↗
2026-09-03Prosor Maya, Chief Business Officer$56,816
1,040 shplan 2026-05-06Form 4s on file end Jun 23144 ↗
2026-08-13Peters John Sheldon, Chief Insurance Officer$578,000
11,000 shplan 2026-03-12Form 4s on file end Jun 23144 ↗
2026-07-07BIXBY TIMOTHY E, Chief Financial Officer$5,780,453
73,000 shplan 2026-03-12Form 4s on file end Jun 23144 ↗
2026-07-06Peters John Sheldon, Chief Insurance Officer$272,076
3,444 shplan 2026-03-12Form 4s on file end Jun 23144 ↗
2026-06-04Peters John Sheldon, Chief Insurance Officer$191,008
3,608 shplan 2025-08-22Form 4s on file end Jun 23144 ↗
2026-06-03Peters John Sheldon, Chief Insurance Officer$92,256
1,735 shplan 2026-03-12144 ↗
Form 4, 2026-06-05: sold 5,343 at $53.01 Form 4 ↗
2026-06-03Prosor Maya, Chief Business Officer$64,871
1,220 shplan 2026-05-06144 ↗
Form 4, 2026-06-05: sold 1,220 at $53.17 Form 4 ↗
2026-06-03BIXBY TIMOTHY E, Chief Financial Officer$118,417
2,227 shplan 2026-03-12144 ↗
Form 4, 2026-06-05: sold 2,227 at $53.17 Form 4 ↗
2026-03-04Peters John Sheldon, Chief Insurance Officer$187,478
3,571 shplan 2025-08-22no Form 4 on file144 ↗
2026-03-03BIXBY TIMOTHY E, Chief Financial Officer$107,011
2,135 shno plan date144 ↗
Form 4, 2026-03-05: sold 2,135 at $50.12 Form 4 ↗
2026-03-03Prosor Maya, Chief Business Officer$11,177
223 shplan 2025-12-12144 ↗
Form 4, 2026-03-05: sold 223 at $50.12 Form 4 ↗
2026-03-03Peters John Sheldon, Chief Insurance Officer$88,867
1,773 shplan 2025-08-22144 ↗
Form 4, 2026-03-05: sold 5,344 at $51.71 Form 4 ↗
2026-01-22Peters John Sheldon, Chief Insurance Officer$810,000
9,000 shplan 2025-08-22144 ↗
Form 4, 2026-01-23: sold 9,000 at $90.00 Form 4 ↗
2026-01-22Daniel Schreiber, Chief Executive Officer$13.9M
144,000 shplan 2024-12-11144 ↗
Form 4, 2026-01-23: sold 126,625 at $94.74 Form 4 ↗
2026-01-06Peters John Sheldon, Chief Insurance Officer$800,000
10,000 shplan 2025-08-22144 ↗
Form 4, 2026-01-08: sold 10,000 at $80.00 Form 4 ↗
2025-12-11Eckstein Adina, Chief Operating Officer$620,612
7,919 shplan 2025-09-08144 ↗
Form 4, 2025-12-15: sold 7,919 at $84.15 Form 4 ↗
2025-12-11Schwartz Debra, Director$351,082
4,200 shno plan date144 ↗
Form 4, 2025-12-15: sold 4,200 at $83.59 Form 4 ↗
2025-12-10Eckstein Adina, Chief Operating Officer$626,947
7,919 shplan 2025-09-08144 ↗
Form 4, 2025-12-11: sold 7,919 at $81.15 Form 4 ↗
2025-12-10Peters John Sheldon, Chief Insurance Officer$287,874
3,554 shplan 2025-08-22144 ↗
Form 4, 2025-12-11: sold 3,554 at $81.00 Form 4 ↗
2025-12-08Eckstein Adina, Chief Operating Officer$5,590,602
70,794 shplan 2025-09-08144 ↗
Form 4, 2025-12-10: sold 70,794 at $78.21 Form 4 ↗
2025-12-03Peters John Sheldon, Chief Insurance Officer$193,011
2,667 shplan 2025-08-22no Form 4 on file144 ↗
2025-12-02BIXBY TIMOTHY E, Chief Financial Officer$208,167
2,862 shno plan date144 ↗
Form 4, 2025-12-04: sold 2,862 at $72.74 Form 4 ↗
2025-12-02Peters John Sheldon, Chief Insurance Officer$194,711
2,677 shplan 2025-08-22144 ↗
Form 4, 2025-12-04: sold 5,344 at $72.56 Form 4 ↗
2025-12-02Prosor Maya, Chief Business Officer$14,401
198 shplan 2025-09-12144 ↗
Form 4, 2025-12-04: sold 198 at $72.74 Form 4 ↗
2025-11-24Peters John Sheldon, Chief Insurance Officer$278,205
3,798 shplan 2025-08-22no Form 4 on file144 ↗
2025-11-20Peters John Sheldon, Chief Insurance Officer$1,377,536
18,930 shplan 2025-08-22144 ↗
Form 4, 2025-11-24: sold 22,728 at $72.85 Form 4 ↗
2025-11-11BIXBY TIMOTHY E, Chief Financial Officer$2,265,144
30,000 shno plan date144 ↗
Form 4, 2025-11-12: sold 30,000 at $75.51 Form 4 ↗
2025-11-10Eckstein Adina, Chief Operating Officer$467,064
5,988 shplan 2025-09-08no Form 4 on file144 ↗
2025-11-07Eckstein Adina, Chief Operating Officer$1,480,000
20,000 shplan 2025-09-08144 ↗
Form 4, 2025-11-12: sold 45,988 at $73.67 Form 4 ↗
2025-11-07Eckstein Adina, Chief Operating Officer$1,440,868
20,000 shplan 2025-09-08no Form 4 on file144 ↗