LMND

Lemonade, Inc.

Insider trading activity for Lemonade, Inc., straight from SEC Form 4 filings. Net figures below count open-market buys and sales only — grants, option exercises and tax withholding are excluded because they are compensation, not decisions to trade.

Past 3 months

-$7M

net selling

Bought(0 · 0 insiders): $0
Sold(7 · 3 insiders): $7M

Past 6 months

-$7.4M

net selling

Bought(0 · 0 insiders): $0
Sold(11 · 3 insiders): $7.4M

Past 12 months

-$37.2M

net selling

Bought(2 · 1 insiders): $485.5K
Sold(37 · 6 insiders): $37.7M

Transaction history

The 100 most recent Form 4 transactions.

Open in screener →

Insider transactions, newest first: date, security, transaction type, size and a link to the filing each row came from.
Date	Insider	Role	Type	Shares	Price	Value	Δ Own	Filing
Sep 4	Peters John Sheldon	Chief Insurance Officer	SSELL◷	2,249	$54.45	$122.5K	-3.0%	Open the original filing on SEC.gov
Sep 3	Prosor Maya	Chief Business Officer	SSELL	1,040	$54.63	$56.8K	-0.5%	Open the original filing on SEC.gov
Sep 3	Peters John Sheldon	Chief Insurance Officer	SSELL◷	859	$54.63	$46.9K	-1.1%	Open the original filing on SEC.gov
Sep 3	Bixby Timothy E	Chief Financial Officer	SSELL	1,893	$54.63	$103.4K	-1.1%	Open the original filing on SEC.gov
Sep 2	Wininger Shai	President	GGIFT	1,876	—	—	<0.1%	Open the original filing on SEC.gov
Aug 13	Peters John Sheldon	Chief Insurance Officer	SSELL	11,000	$52.55	$578.1K	-12.5%	Open the original filing on SEC.gov
Jul 27	Peters John Sheldon	Chief Insurance Officer	AGRANT	10,000	—	—	+12.8%	Open the original filing on SEC.gov
Jul 7	Bixby Timothy E	Chief Financial Officer	SSELL◷	73,000	$79.18	$5.8M	-29.5%	Open the original filing on SEC.gov
Jul 6	Peters John Sheldon	Chief Insurance Officer	SSELL◷?	3,444	$79.00	$272.1K	-4.2%	Open the original filing on SEC.gov
Jun 10	Eisenberg Michael A	Director	GGIFT	5,000	—	—	-2.5%	Open the original filing on SEC.gov
Jun 4	Peters John Sheldon	Chief Insurance Officer	SSELL◷	3,608	$52.94	$191K	-4.3%	Open the original filing on SEC.gov
Jun 3	Ratanchandani Prashant	Director	AGRANT	2,848	—	—	+85.4%	Open the original filing on SEC.gov
Jun 3	Seeley Geoff	Director	AGRANT	2,848	—	—	+91.3%	Open the original filing on SEC.gov
Jun 3	Prosor Maya	Chief Business Officer	SSELL	1,220	$53.17	$64.9K	-0.7%	Open the original filing on SEC.gov
Jun 3	Schwartz Debra	Director	AGRANT	2,848	—	—	+13.2%	Open the original filing on SEC.gov
Jun 3	Peters John Sheldon	Chief Insurance Officer	SSELL◷	1,735	$53.17	$92.2K	-2.0%	Open the original filing on SEC.gov
Jun 3	Haj-Yehia Samer	Director	AGRANT	2,848	—	—	+11.7%	Open the original filing on SEC.gov
Jun 3	Bixby Timothy E	Chief Financial Officer	SSELL	2,227	$53.17	$118.4K	-0.9%	Open the original filing on SEC.gov
Jun 3	Angelidis-Smith Maria	Director	AGRANT	2,848	—	—	+19.1%	Open the original filing on SEC.gov
Mar 18	Schreiber Daniel A.	Chief Executive Officer	AGRANT	180,000	—	—	+21.3%	Open the original filing on SEC.gov
Mar 18	Schreiber Daniel A.	Chief Executive Officer	AGRANT	820,000	—	—	+3,371%	Open the original filing on SEC.gov
Mar 18	Wininger Shai	President	AGRANT	180,000	—	—	+4.3%	Open the original filing on SEC.gov
Mar 18	Wininger Shai	President	AGRANT	820,000	—	—	+24.0%	Open the original filing on SEC.gov
Mar 10	Angelidis-Smith Maria	Director	PBUY↺	5,390	$55.70	$300.2K	+16.1%	Open the original filing on SEC.gov
Mar 10	Angelidis-Smith Maria	Director	PBUY↺★	3,350	$55.30	$185.3K	+29.0%	Open the original filing on SEC.gov
Mar 8	Prosor Maya	Chief Business Officer	AGRANT	181,389	—	—	+2,450%	Open the original filing on SEC.gov
Mar 8	Eckstein Adina	Chief Operating Officer	AGRANT◆	54,417	—	—	—	Open the original filing on SEC.gov
Mar 8	Eckstein Adina	Chief Operating Officer	AGRANT	145,112	—	—	+77.0%	Open the original filing on SEC.gov
Mar 4	Peters John Sheldon	Chief Insurance Officer	SSELL◷	3,571	$52.50	$187.5K	-4.5%	Open the original filing on SEC.gov
Mar 3	Prosor Maya	Chief Business Officer	SSELL	223	$50.12	$11.2K	-2.9%	Open the original filing on SEC.gov
Mar 3	Peters John Sheldon	Chief Insurance Officer	SSELL◷	1,773	$50.12	$88.9K	-2.2%	Open the original filing on SEC.gov
Mar 3	Bixby Timothy E	Chief Financial Officer	SSELL	2,135	$50.12	$107K	-0.9%	Open the original filing on SEC.gov
Feb 12	Peters John Sheldon	Chief Insurance Officer	MEXER◆	11,845	$11.61	$137.5K	—	Open the original filing on SEC.gov
Feb 12	Peters John Sheldon	Chief Insurance Officer	MEXER	11,845	$11.61	$137.5K	+16.9%	Open the original filing on SEC.gov
Jan 23	Schreiber Daniel A.	Chief Executive Officer	SSELL◷	9,108	$99.04	$902.1K	-0.6%	Open the original filing on SEC.gov
Jan 22	Peters John Sheldon	Chief Insurance Officer	SSELL◷	9,000	$90.00	$810K	-11.4%	Open the original filing on SEC.gov
Jan 22	Schreiber Daniel A.	Chief Executive Officer	SSELL◷	126,625	$94.74	$12M	-7.7%	Open the original filing on SEC.gov
Jan 8	Peters John Sheldon	Chief Insurance Officer	MEXER◆	18,457	$5.26	$97.1K	—	Open the original filing on SEC.gov
Jan 8	Peters John Sheldon	Chief Insurance Officer	MEXER	18,457	$5.26	$97.1K	+30.4%	Open the original filing on SEC.gov
Jan 6	Peters John Sheldon	Chief Insurance Officer	SSELL◷	10,000	$80.00	$800K	-14.1%	Open the original filing on SEC.gov
Dec 11, 2025	Schwartz Debra	Director	SSELL	4,200	$83.59	$351.1K	-16.3%	Open the original filing on SEC.gov
Dec 11, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	7,919	$84.15	$666.4K	-4.0%	Open the original filing on SEC.gov
Dec 10, 2025	Peters John Sheldon	Chief Insurance Officer	SSELL	3,554	$81.00	$287.9K	-4.8%	Open the original filing on SEC.gov
Dec 10, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	7,919	$81.15	$642.6K	-3.9%	Open the original filing on SEC.gov
Dec 9, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷◆	29,237	$44.57	$1.3M	—	Open the original filing on SEC.gov
Dec 9, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	29,237	$77.17	$2.3M	-12.5%	Open the original filing on SEC.gov
Dec 9, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	29,237	$44.57	$1.3M	+14.3%	Open the original filing on SEC.gov
Dec 8, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷◆	1,549	$44.57	$69K	—	Open the original filing on SEC.gov
Dec 8, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷◆	16,250	$24.47	$397.6K	—	Open the original filing on SEC.gov
Dec 8, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	7,919	$78.94	$625.1K	-3.7%	Open the original filing on SEC.gov
Dec 8, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	15,839	$78.92	$1.3M	-7.0%	Open the original filing on SEC.gov
Dec 8, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	17,799	$78.97	$1.4M	-7.2%	Open the original filing on SEC.gov
Dec 8, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	1,549	$44.57	$69K	+0.6%	Open the original filing on SEC.gov
Dec 8, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	16,250	$24.47	$397.6K	+7.1%	Open the original filing on SEC.gov
Dec 3, 2025	Peters John Sheldon	Chief Insurance Officer	SSELL◷	2,667	$72.37	$193K	-3.5%	Open the original filing on SEC.gov
Dec 2, 2025	Prosor Maya	Chief Business Officer	SSELL	198	$72.74	$14.4K	-2.5%	Open the original filing on SEC.gov
Dec 2, 2025	Peters John Sheldon	Chief Insurance Officer	SSELL◷	2,677	$72.74	$194.7K	-3.4%	Open the original filing on SEC.gov
Dec 2, 2025	Bixby Timothy E	Chief Financial Officer	SSELL	2,862	$72.74	$208.2K	-1.1%	Open the original filing on SEC.gov
Nov 24, 2025	Peters John Sheldon	Chief Insurance Officer	SSELL◷	3,798	$73.25	$278.2K	-4.5%	Open the original filing on SEC.gov
Nov 20, 2025	Peters John Sheldon	Chief Insurance Officer	SSELL◷	18,930	$72.77	$1.4M	-18.5%	Open the original filing on SEC.gov
Nov 11, 2025	Schreiber Daniel A.	Chief Executive Officer	GGIFT	35,000	—	—	-59.0%	Open the original filing on SEC.gov
Nov 11, 2025	Bixby Timothy E	Chief Financial Officer	SSELL	30,000	$75.51	$2.3M	-100.0%	Open the original filing on SEC.gov
Nov 10, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷◆	5,988	$27.35	$163.8K	—	Open the original filing on SEC.gov
Nov 10, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	5,988	$78.00	$467.1K	-2.6%	Open the original filing on SEC.gov
Nov 10, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	5,988	$27.35	$163.8K	+2.6%	Open the original filing on SEC.gov
Nov 7, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷◆	40,000	$27.35	$1.1M	—	Open the original filing on SEC.gov
Nov 7, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	20,000	$74.00	$1.5M	-8.1%	Open the original filing on SEC.gov
Nov 7, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	20,000	$27.35	$547K	+8.8%	Open the original filing on SEC.gov
Nov 7, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	20,000	$72.04	$1.4M	-8.1%	Open the original filing on SEC.gov
Nov 7, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	20,000	$27.35	$547K	+8.8%	Open the original filing on SEC.gov
Nov 7, 2025	Bixby Timothy E	Chief Financial Officer	GGIFT	6,000	—	—	-2.3%	Open the original filing on SEC.gov
Oct 16, 2025	Ratanchandani Prashant	Director	AGRANT	3,337	—	—	—	Open the original filing on SEC.gov
Oct 7, 2025	Seeley Geoff	Director	AGRANT	3,119	—	—	—	Open the original filing on SEC.gov
Sep 12, 2025	Eisenberg Michael A	Director	GGIFT	4,000	—	—	-2.0%	Open the original filing on SEC.gov
Sep 3, 2025	Prosor Maya	Chief Business Officer	SSELL	282	$50.34	$14.2K	-3.5%	Open the original filing on SEC.gov
Sep 3, 2025	Peters John Sheldon	Chief Insurance Officer	SSELL	2,718	$50.34	$136.8K	-2.6%	Open the original filing on SEC.gov
Sep 3, 2025	Bixby Timothy E	Chief Financial Officer	SSELL	2,906	$50.34	$146.3K	-1.1%	Open the original filing on SEC.gov
Aug 21, 2025	Prosor Maya	Chief Business Officer	AGRANT◆	76,668	—	—	—	Open the original filing on SEC.gov
Aug 21, 2025	Peters John Sheldon	Chief Insurance Officer	AGRANT◆	25,556	—	—	—	Open the original filing on SEC.gov
Aug 21, 2025	Schreiber Daniel A.	Chief Executive Officer	AGRANT◆	127,780	—	—	—	Open the original filing on SEC.gov
Aug 21, 2025	Wininger Shai	President	AGRANT◆	127,780	—	—	—	Open the original filing on SEC.gov
Aug 21, 2025	Eckstein Adina	Chief Operating Officer	AGRANT	38,334	—	—	+20.2%	Open the original filing on SEC.gov
Aug 21, 2025	Bixby Timothy E	Chief Financial Officer	AGRANT◆	127,780	—	—	—	Open the original filing on SEC.gov
Aug 13, 2025	Peters John Sheldon	Chief Insurance Officer	MEXER◆	38,155	$11.61	$443K	—	Open the original filing on SEC.gov
Aug 13, 2025	Peters John Sheldon	Chief Insurance Officer	SSELL◷?	38,155	$60.00	$2.3M	-26.6%	Open the original filing on SEC.gov
Aug 13, 2025	Peters John Sheldon	Chief Insurance Officer	MEXER	38,155	$11.61	$443K	+36.3%	Open the original filing on SEC.gov
Aug 13, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷◆	5,000	$24.47	$122.4K	—	Open the original filing on SEC.gov
Aug 13, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	5,000	$58.00	$290K	-2.6%	Open the original filing on SEC.gov
Aug 13, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	5,000	$24.47	$122.4K	+2.7%	Open the original filing on SEC.gov
Aug 12, 2025	Peters John Sheldon	Chief Insurance Officer	GGIFT	1,000	—	—	-0.9%	Open the original filing on SEC.gov
Aug 11, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷◆	5,000	$24.47	$122.4K	—	Open the original filing on SEC.gov
Aug 11, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	0	$53.00	$0	—	Open the original filing on SEC.gov
Aug 11, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	0	$24.47	$0	—	Open the original filing on SEC.gov
Aug 5, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷◆	3,750	$24.47	$91.8K	—	Open the original filing on SEC.gov
Aug 5, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷◆	1,250	$23.69	$29.6K	—	Open the original filing on SEC.gov
Aug 5, 2025	Eckstein Adina	Chief Operating Officer	SSELL◷	5,000	$49.00	$245K	-2.6%	Open the original filing on SEC.gov
Aug 5, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	3,750	$23.69	$88.8K	+2.0%	Open the original filing on SEC.gov
Aug 5, 2025	Eckstein Adina	Chief Operating Officer	MEXER◷	1,250	$23.69	$29.6K	+0.7%	Open the original filing on SEC.gov
Jul 21, 2025	Bixby Timothy E	Chief Financial Officer	MEXER◷◆	1,000	$23.69	$23.7K	—	Open the original filing on SEC.gov
Jul 21, 2025	Bixby Timothy E	Chief Financial Officer	SSELL◷	1,000	$42.70	$42.7K	-0.4%	Open the original filing on SEC.gov

SSELL◷$122.5K

Peters John Sheldon · Chief Insurance…Sep 4

2,249 sh @ $54.45 · -3.0% own

SSELL$56.8K

Prosor Maya · Chief Business…Sep 3

1,040 sh @ $54.63 · -0.5% own

SSELL◷$46.9K

Peters John Sheldon · Chief Insurance…Sep 3

859 sh @ $54.63 · -1.1% own

SSELL$103.4K

Bixby Timothy E · Chief Financial…Sep 3

1,893 sh @ $54.63 · -1.1% own

GGIFT—

Wininger Shai · PresidentSep 2

1,876 sh · <0.1% own

SSELL$578.1K

Peters John Sheldon · Chief Insurance…Aug 13

11,000 sh @ $52.55 · -12.5% own

AGRANT—

Peters John Sheldon · Chief Insurance…Jul 27

10,000 sh · +12.8% own

SSELL◷$5.8M

Bixby Timothy E · Chief Financial…Jul 7

73,000 sh @ $79.18 · -29.5% own

SSELL◷?$272.1K

Peters John Sheldon · Chief Insurance…Jul 6

3,444 sh @ $79.00 · -4.2% own

GGIFT—

Eisenberg Michael A · DirectorJun 10

5,000 sh · -2.5% own

SSELL◷$191K

Peters John Sheldon · Chief Insurance…Jun 4

3,608 sh @ $52.94 · -4.3% own

AGRANT—

Ratanchandani Prashant · DirectorJun 3

2,848 sh · +85.4% own

AGRANT—

Seeley Geoff · DirectorJun 3

2,848 sh · +91.3% own

SSELL$64.9K

Prosor Maya · Chief Business…Jun 3

1,220 sh @ $53.17 · -0.7% own

AGRANT—

Schwartz Debra · DirectorJun 3

2,848 sh · +13.2% own

SSELL◷$92.2K

Peters John Sheldon · Chief Insurance…Jun 3

1,735 sh @ $53.17 · -2.0% own

AGRANT—

Haj-Yehia Samer · DirectorJun 3

2,848 sh · +11.7% own

SSELL$118.4K

Bixby Timothy E · Chief Financial…Jun 3

2,227 sh @ $53.17 · -0.9% own

AGRANT—

Angelidis-Smith Maria · DirectorJun 3

2,848 sh · +19.1% own

AGRANT—

Schreiber Daniel A. · Chief Executive…Mar 18

180,000 sh · +21.3% own

AGRANT—

Schreiber Daniel A. · Chief Executive…Mar 18

820,000 sh · +3,371% own

AGRANT—

Wininger Shai · PresidentMar 18

180,000 sh · +4.3% own

AGRANT—

Wininger Shai · PresidentMar 18

820,000 sh · +24.0% own

PBUY↺$300.2K

Angelidis-Smith Maria · DirectorMar 10

5,390 sh @ $55.70 · +16.1% own

PBUY↺★$185.3K

Angelidis-Smith Maria · DirectorMar 10

3,350 sh @ $55.30 · +29.0% own

AGRANT—

Prosor Maya · Chief Business…Mar 8

181,389 sh · +2,450% own

AGRANT◆—

Eckstein Adina · Chief Operating…Mar 8

54,417 sh

AGRANT—

Eckstein Adina · Chief Operating…Mar 8

145,112 sh · +77.0% own

SSELL◷$187.5K

Peters John Sheldon · Chief Insurance…Mar 4

3,571 sh @ $52.50 · -4.5% own

SSELL$11.2K

Prosor Maya · Chief Business…Mar 3

223 sh @ $50.12 · -2.9% own

SSELL◷$88.9K

Peters John Sheldon · Chief Insurance…Mar 3

1,773 sh @ $50.12 · -2.2% own

SSELL$107K

Bixby Timothy E · Chief Financial…Mar 3

2,135 sh @ $50.12 · -0.9% own

MEXER◆$137.5K

Peters John Sheldon · Chief Insurance…Feb 12

11,845 sh @ $11.61

MEXER$137.5K

Peters John Sheldon · Chief Insurance…Feb 12

11,845 sh @ $11.61 · +16.9% own

SSELL◷$902.1K

Schreiber Daniel A. · Chief Executive…Jan 23

9,108 sh @ $99.04 · -0.6% own

SSELL◷$810K

Peters John Sheldon · Chief Insurance…Jan 22

9,000 sh @ $90.00 · -11.4% own

SSELL◷$12M

Schreiber Daniel A. · Chief Executive…Jan 22

126,625 sh @ $94.74 · -7.7% own

MEXER◆$97.1K

Peters John Sheldon · Chief Insurance…Jan 8

18,457 sh @ $5.26

MEXER$97.1K

Peters John Sheldon · Chief Insurance…Jan 8

18,457 sh @ $5.26 · +30.4% own

SSELL◷$800K

Peters John Sheldon · Chief Insurance…Jan 6

10,000 sh @ $80.00 · -14.1% own

SSELL$351.1K

Schwartz Debra · DirectorDec 11, 2025

4,200 sh @ $83.59 · -16.3% own

SSELL◷$666.4K

Eckstein Adina · Chief Operating…Dec 11, 2025

7,919 sh @ $84.15 · -4.0% own

SSELL$287.9K

Peters John Sheldon · Chief Insurance…Dec 10, 2025

3,554 sh @ $81.00 · -4.8% own

SSELL◷$642.6K

Eckstein Adina · Chief Operating…Dec 10, 2025

7,919 sh @ $81.15 · -3.9% own

MEXER◷◆$1.3M

Eckstein Adina · Chief Operating…Dec 9, 2025

29,237 sh @ $44.57

SSELL◷$2.3M

Eckstein Adina · Chief Operating…Dec 9, 2025

29,237 sh @ $77.17 · -12.5% own

MEXER◷$1.3M

Eckstein Adina · Chief Operating…Dec 9, 2025

29,237 sh @ $44.57 · +14.3% own

MEXER◷◆$69K