Lemonade Inc. (LMND) Insider Trading

Last 12 months

Insiders bought $485k and sold $37.7M on the open market.

89% of the selling was scheduled in advance under 10b5-1 plans. Chief Financial Officer Timothy E Bixby sold $2.27M on Nov 11, 2025, 11% of their stake, outside a plan.

Net open-market

−$37.2M

1 buy · 27 sales

Under a 10b5-1 plan

89%

of the value sold

Insiders who bought / sold

1 / 6

executives and directors

Last open-market buy

Mar 2026

Mar 10, 2026

Get an email when LMND's executives or directors buy, or make a large sale outside a plan.

Trades · last 2 years

Date	Insider	Trade	Shares	Price	Value	Of their stake	Filing
Sep 3 – 4	John Sheldon Peters Chief Insurance Officer	Sold10b5-1 plan 2 parts	3,108	$54.50 average	$169k	4.0%	Form 4
Sep 3	Maya Prosor Chief Business Officer	SoldNo plan	1,040	$54.63	$57k	0.5%	Form 4
Sep 3	Timothy E Bixby Chief Financial Officer	SoldNo plan	1,893	$54.63	$103k	1.1%	Form 4
Aug 13	John Sheldon Peters Chief Insurance Officer	SoldNo plan	11,000	$52.55	$578k	13%	Form 4
Jul 7	Timothy E Bixby Chief Financial Officer	Sold10b5-1 plan	73,000	$79.18	$5.78M	30%	Form 4
Jul 6	John Sheldon Peters Chief Insurance Officer	Sold10b5-1 plan	3,444	$79.00	$272k	4.2%	Form 4
Jun 3 – 4	John Sheldon Peters Chief Insurance Officer	Sold10b5-1 plan 2 parts	5,343	$53.01 average	$283k	6.2%	Form 4
Jun 3	Maya Prosor Chief Business Officer	SoldNo plan	1,220	$53.17	$65k	0.6%	Form 4
Jun 3	Timothy E Bixby Chief Financial Officer	SoldNo plan	2,227	$53.17	$118k	0.9%	Form 4
Mar 10	Maria Angelidis-Smith Director	Bought 2 parts	8,740	$55.55 average	$485k	19%	Form 4
Mar 3 – 4	John Sheldon Peters Chief Insurance Officer	Sold10b5-1 plan 2 parts	5,344	$51.71 average	$276k	6.5%	Form 4
Mar 3	Maya Prosor Chief Business Officer	SoldNo plan	223	$50.12	$11k	0.6%	Form 4
Mar 3	Timothy E Bixby Chief Financial Officer	SoldNo plan	2,135	$50.12	$107k	0.8%	Form 4
Jan 23	Daniel A. Schreiber Chief Executive Officer	Sold10b5-1 plan	9,108	$99.04	$902k	0.6%	Form 4
Jan 22	John Sheldon Peters Chief Insurance Officer	Sold10b5-1 plan	9,000	$90.00	$810k	11%	Form 4
Jan 22	Daniel A. Schreiber Chief Executive Officer	Sold10b5-1 plan	126,625	$94.74	$12M	7.7%	Form 4
Jan 6	John Sheldon Peters Chief Insurance Officer	Sold10b5-1 plan	10,000	$80.00	$800k	14%	Form 4
Dec 11, 2025	Debra Schwartz Director	SoldNo plan	4,200	$83.59	$351k	16%	Form 4
Dec 11, 2025	Adina Eckstein Chief Operating Officer	Sold10b5-1 plan	7,919	$84.15	$666k	4.0%	Form 4
Dec 10, 2025	Adina Eckstein Chief Operating Officer	Sold10b5-1 plan	7,919	$81.15	$643k	3.9%	Form 4
Dec 10, 2025	John Sheldon Peters Chief Insurance Officer	SoldNo plan	3,554	$81.00	$288k	4.8%	Form 4
Dec 8, 2025 – Dec 9, 2025	Adina Eckstein Chief Operating Officer	Sold10b5-1 plan 4 parts	70,794	$78.21 average	$5.54M	26%	Form 4
Dec 2, 2025 – Dec 3, 2025	John Sheldon Peters Chief Insurance Officer	Sold10b5-1 plan 2 parts	5,344	$72.56 average	$388k	6.7%	Form 4
Dec 2, 2025	Maya Prosor Chief Business Officer	SoldNo plan	198	$72.74	$14k	0.5%	Form 4
Dec 2, 2025	Timothy E Bixby Chief Financial Officer	SoldNo plan	2,862	$72.74	$208k	1.1%	Form 4
Nov 20, 2025 – Nov 24, 2025	John Sheldon Peters Chief Insurance Officer	Sold10b5-1 plan 2 parts	22,728	$72.85 average	$1.66M	22%	Form 4
Nov 11, 2025	Timothy E Bixby Chief Financial Officer	SoldNo plan	30,000	$75.51	$2.27M	11%	Form 4
Nov 7, 2025 – Nov 10, 2025	Adina Eckstein Chief Operating Officer	Sold10b5-1 plan 3 parts	45,988	$73.67 average	$3.39M	17%	Form 4
Sep 3, 2025	Maya Prosor Chief Business Officer	SoldNo plan	282	$50.34	$14k	0.8%	Form 4
Sep 3, 2025	John Sheldon Peters Chief Insurance Officer	SoldNo plan	2,718	$50.34	$137k	2.6%	Form 4
Sep 3, 2025	Timothy E Bixby Chief Financial Officer	SoldNo plan	2,906	$50.34	$146k	1.0%	Form 4
Aug 13, 2025	John Sheldon Peters Chief Insurance Officer	Sold10b5-1 plan	38,155	$60.00	$2.29M	27%	Form 4
Aug 13, 2025	Adina Eckstein Chief Operating Officer	Sold10b5-1 plan	5,000	$58.00	$290k	2.6%	Form 4
Aug 11, 2025	Adina Eckstein Chief Operating Officer	Sold10b5-1 plan	0	—	$0	—	Form 4
Aug 5, 2025	Adina Eckstein Chief Operating Officer	Sold10b5-1 plan	5,000	$49.00	$245k	2.6%	Form 4
Jul 18, 2025 – Jul 21, 2025	Timothy E Bixby Chief Financial Officer	Sold10b5-1 plan 2 parts	7,000	$42.53 average	$298k	2.3%	Form 4
Jul 14, 2025	Timothy E Bixby Chief Financial Officer	Sold10b5-1 plan	5,000	$38.16	$191k	1.7%	Form 4
Jul 7, 2025	Timothy E Bixby Chief Financial Officer	Sold10b5-1 plan 2 parts	11,000	$42.40 average	$466k	3.6%	Form 4
Jun 30, 2025	Timothy E Bixby Chief Financial Officer	Sold10b5-1 plan	11,000	$42.69	$470k	3.6%	Form 4
Jun 23, 2025	Adina Eckstein Chief Operating Officer	Sold10b5-1 plan	5,000	$45.00	$225k	2.6%	Form 4

Sep 3 – 410b5-1 plan
John Sheldon Peters
Chief Insurance Officer · sold 3,108 at avg $54.50
$169k
4.0% of stake
Sep 3No plan
Maya Prosor
Chief Business Officer · sold 1,040 at $54.63
$57k
0.5% of stake
Sep 3No plan
Timothy E Bixby
Chief Financial Officer · sold 1,893 at $54.63
$103k
1.1% of stake
Aug 13No plan
John Sheldon Peters
Chief Insurance Officer · sold 11,000 at $52.55
$578k
13% of stake
Jul 710b5-1 plan
Timothy E Bixby
Chief Financial Officer · sold 73,000 at $79.18
$5.78M
30% of stake
Jul 610b5-1 plan
John Sheldon Peters
Chief Insurance Officer · sold 3,444 at $79.00
$272k
4.2% of stake
Jun 3 – 410b5-1 plan
John Sheldon Peters
Chief Insurance Officer · sold 5,343 at avg $53.01
$283k
6.2% of stake
Jun 3No plan
Maya Prosor
Chief Business Officer · sold 1,220 at $53.17
$65k
0.6% of stake
Jun 3No plan
Timothy E Bixby
Chief Financial Officer · sold 2,227 at $53.17
$118k
0.9% of stake
Mar 10
Maria Angelidis-Smith
Director · bought 8,740 at avg $55.55
$485k
19% of stake
Mar 3 – 410b5-1 plan
John Sheldon Peters
Chief Insurance Officer · sold 5,344 at avg $51.71
$276k
6.5% of stake
Mar 3No plan
Maya Prosor
Chief Business Officer · sold 223 at $50.12
$11k
0.6% of stake
Mar 3No plan
Timothy E Bixby
Chief Financial Officer · sold 2,135 at $50.12
$107k
0.8% of stake
Jan 2310b5-1 plan
Daniel A. Schreiber
Chief Executive Officer · sold 9,108 at $99.04
$902k
0.6% of stake
Jan 2210b5-1 plan
John Sheldon Peters
Chief Insurance Officer · sold 9,000 at $90.00
$810k
11% of stake
Jan 2210b5-1 plan
Daniel A. Schreiber
Chief Executive Officer · sold 126,625 at $94.74
$12M
7.7% of stake
Jan 610b5-1 plan
John Sheldon Peters
Chief Insurance Officer · sold 10,000 at $80.00
$800k
14% of stake
Dec 11, 2025No plan
Debra Schwartz
Director · sold 4,200 at $83.59
$351k
16% of stake
Dec 11, 202510b5-1 plan
Adina Eckstein
Chief Operating Officer · sold 7,919 at $84.15
$666k
4.0% of stake
Dec 10, 202510b5-1 plan
Adina Eckstein
Chief Operating Officer · sold 7,919 at $81.15
$643k
3.9% of stake
Dec 10, 2025No plan
John Sheldon Peters
Chief Insurance Officer · sold 3,554 at $81.00
$288k
4.8% of stake
Dec 8, 2025 – Dec 9, 202510b5-1 plan
Adina Eckstein
Chief Operating Officer · sold 70,794 at avg $78.21
$5.54M
26% of stake
Dec 2, 2025 – Dec 3, 202510b5-1 plan
John Sheldon Peters
Chief Insurance Officer · sold 5,344 at avg $72.56
$388k
6.7% of stake
Dec 2, 2025No plan
Maya Prosor
Chief Business Officer · sold 198 at $72.74
$14k
0.5% of stake
Dec 2, 2025No plan
Timothy E Bixby
Chief Financial Officer · sold 2,862 at $72.74
$208k
1.1% of stake
Nov 20, 2025 – Nov 24, 202510b5-1 plan
John Sheldon Peters
Chief Insurance Officer · sold 22,728 at avg $72.85
$1.66M
22% of stake
Nov 11, 2025No plan
Timothy E Bixby
Chief Financial Officer · sold 30,000 at $75.51
$2.27M
11% of stake
Nov 7, 2025 – Nov 10, 202510b5-1 plan
Adina Eckstein
Chief Operating Officer · sold 45,988 at avg $73.67
$3.39M
17% of stake
Sep 3, 2025No plan
Maya Prosor
Chief Business Officer · sold 282 at $50.34
$14k
0.8% of stake
Sep 3, 2025No plan
John Sheldon Peters
Chief Insurance Officer · sold 2,718 at $50.34
$137k
2.6% of stake
Sep 3, 2025No plan
Timothy E Bixby
Chief Financial Officer · sold 2,906 at $50.34
$146k
1.0% of stake
Aug 13, 202510b5-1 plan
John Sheldon Peters
Chief Insurance Officer · sold 38,155 at $60.00
$2.29M
27% of stake
Aug 13, 202510b5-1 plan
Adina Eckstein
Chief Operating Officer · sold 5,000 at $58.00
$290k
2.6% of stake
Aug 11, 202510b5-1 plan
Adina Eckstein
Chief Operating Officer · sold 0
$0
— of stake
Aug 5, 202510b5-1 plan
Adina Eckstein
Chief Operating Officer · sold 5,000 at $49.00
$245k
2.6% of stake
Jul 18, 2025 – Jul 21, 202510b5-1 plan
Timothy E Bixby
Chief Financial Officer · sold 7,000 at avg $42.53
$298k
2.3% of stake
Jul 14, 202510b5-1 plan
Timothy E Bixby
Chief Financial Officer · sold 5,000 at $38.16
$191k
1.7% of stake
Jul 7, 202510b5-1 plan
Timothy E Bixby
Chief Financial Officer · sold 11,000 at avg $42.40
$466k
3.6% of stake
Jun 30, 202510b5-1 plan
Timothy E Bixby
Chief Financial Officer · sold 11,000 at $42.69
$470k
3.6% of stake
Jun 23, 202510b5-1 plan
Adina Eckstein
Chief Operating Officer · sold 5,000 at $45.00
$225k
2.6% of stake

How to read this. Insiders sell for many reasons: taxes, diversifying, a house. Open-market buys are rarer and say more. A 10b5-1 plan is a trading schedule set up months in advance, so those sales were not timed on news. Large holders (funds and 10% owners) are listed under Everything but not counted as insiders. If you own or watch LMND, we send a push when an executive buys or makes a large sale outside a plan.

Source: SEC Form 4 filings, filed within two business days of each trade and checked for new ones every hour.

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Spot a number that looks wrong? Check it in LMND's SEC filings or

Download this analysis as a PDF (Pro)

Data sourced from SEC EDGAR filings and third-party price providers. Scores, valuations, and metrics are algorithmic estimates. This is not investment advice. See our Terms and Methodology.

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