Insider Transactions last 24 months for Lemonade, Inc. - NYSE: LMND
Transactions
All
Buy
Sell
Option Exercise
Filer's Name
Relationship/ Title
Trans.
Date
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Value
Total Shares Owned
Wininger Shai President 03/18/2026 AA Direct COM 180,000 $0.00 $0.00 4,418,749 Wininger Shai President 03/18/2026 AA Direct COM 820,000 $0.00 $0.00 4,238,749 Schreiber Daniel A. Chief Executive Officer 03/18/2026 AA Direct COM 180,000 $0.00 $0.00 1,024,327 Schreiber Daniel A. Chief Executive Officer 03/18/2026 AA Direct COM 820,000 $0.00 $0.00 844,327 Angelidis-Smith Maria Director 03/10/2026 AA Indirect COM 5,390 $55.70 $300,223.00 38,944 Angelidis-Smith Maria Director 03/10/2026 AA Direct COM 3,350 $55.30 $185,255.00 14,896 Eckstein Adina Chief Operating Officer 03/08/2026 AA Direct COM 145,112 $0.00 $0.00 333,503 Prosor Maya Chief Business Officer 03/08/2026 AA Direct COM 181,389 $0.00 $0.00 188,793 Peters John Sheldon Chief Insurance Officer 03/04/2026 DS Direct COM 3,571 $52.50 $187,477.50 76,729 Bixby Timothy E Chief Financial Officer 03/03/2026 DS Direct COM 2,135 $50.12 $107,006.20 249,490 Peters John Sheldon Chief Insurance Officer 03/03/2026 DS Direct COM 1,773 $50.12 $88,862.76 80,300 Prosor Maya Chief Business Officer 03/03/2026 DS Direct COM 223 $50.12 $11,176.76 7,404 Peters John Sheldon Chief Insurance Officer 02/12/2026 AM Direct COM 11,845 $11.61 $137,520.45 82,073 Schreiber Daniel A. Chief Executive Officer 01/23/2026 DS Indirect COM 9,108 $99.04 $902,056.32 1,514,426 Schreiber Daniel A. Chief Executive Officer 01/22/2026 DS Indirect COM 126,625 $94.74 $11,996,452.50 1,523,534 Peters John Sheldon Chief Insurance Officer 01/22/2026 DS Direct COM 9,000 $90.00 $810,000.00 70,228 Peters John Sheldon Chief Insurance Officer 01/08/2026 AM Direct COM 18,457 $5.26 $97,083.82 79,228 Peters John Sheldon Chief Insurance Officer 01/06/2026 DS Direct COM 10,000 $80.00 $800,000.00 60,771 Eckstein Adina Chief Operating Officer 12/11/2025 DS Direct COM 7,919 $84.15 $666,383.85 188,391 Schwartz Debra Director 12/11/2025 DS Direct COM 4,200 $83.59 $351,078.00 21,567 Peters John Sheldon Chief Insurance Officer 12/10/2025 DS Direct COM 3,554 $81.00 $287,874.00 70,771 Eckstein Adina Chief Operating Officer 12/10/2025 DS Direct COM 7,919 $81.15 $642,626.85 196,310 Eckstein Adina Chief Operating Officer 12/09/2025 DS Direct COM 29,237 $77.17 $2,256,219.29 204,229 Eckstein Adina Chief Operating Officer 12/09/2025 AM Direct COM 29,237 $44.57 $1,303,093.09 233,466 Eckstein Adina Chief Operating Officer 12/08/2025 DS Direct COM 7,919 $78.94 $625,125.86 204,229
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Filer's Name
Relationship/ Title
Trans.
Date
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Value
Total Shares Owned
Wininger Shai President 03/18/2026 AA Direct COM 180,000 $0.00 $0.00 4,418,749 Wininger Shai President 03/18/2026 AA Direct COM 820,000 $0.00 $0.00 4,238,749 Schreiber Daniel A. Chief Executive Officer 03/18/2026 AA Direct COM 180,000 $0.00 $0.00 1,024,327 Schreiber Daniel A. Chief Executive Officer 03/18/2026 AA Direct COM 820,000 $0.00 $0.00 844,327 Angelidis-Smith Maria Director 03/10/2026 AA Indirect COM 5,390 $55.70 $300,223.00 38,944 Angelidis-Smith Maria Director 03/10/2026 AA Direct COM 3,350 $55.30 $185,255.00 14,896 Eckstein Adina Chief Operating Officer 03/08/2026 AA Direct COM 145,112 $0.00 $0.00 333,503 Prosor Maya Chief Business Officer 03/08/2026 AA Direct COM 181,389 $0.00 $0.00 188,793 Ratanchandani Prashant Director 10/16/2025 AA Direct COM 3,337 $0.00 $0.00 3,337 Seeley Geoff Director 10/07/2025 AA Direct COM 3,119 $0.00 $0.00 3,119 Eckstein Adina Chief Operating Officer 08/21/2025 AA Direct COM 38,334 $0.00 $0.00 227,987 Angelidis-Smith Maria Director 06/10/2025 AA Direct COM 4,184 $0.00 $0.00 11,546 Schwartz Debra Director 06/10/2025 AA Direct COM 4,184 $0.00 $0.00 25,767 Haj-Yehia Samer Director 06/10/2025 AA Direct COM 4,184 $0.00 $0.00 24,339 Angelidis-Smith Maria Director 11/13/2024 AP Indirect COM 15,042 $33.23 $499,845.66 33,554 Angelidis-Smith Maria Director 11/08/2024 AP Indirect COM 18,512 $27.42 $507,599.04 18,512 Angelidis-Smith Maria Director 10/31/2024 AA Direct COM 7,362 $23.77 $174,994.74 7,362 Haj-Yehia Samer Director 06/24/2024 AA Direct COM 9,231 $0.00 $0.00 20,155 Eckstein Adina Chief Operating Officer 06/24/2024 AA Direct COM 53,667 $0.00 $0.00 189,653 Peters John Sheldon Chief Insurance Officer 06/24/2024 AA Direct COM 17,889 $0.00 $0.00 91,830 Schwartz Debra Director 06/24/2024 AA Direct COM 9,231 $0.00 $0.00 21,583 Nyatta Mwashuma Kamata Director 06/24/2024 AA Direct COM 9,231 $16.25 $150,003.75 23,189 Bixby Timothy E Chief Financial Officer 06/14/2024 AP Indirect COM 5,000 $14.40 $72,000.00 30,000 Bixby Timothy E Chief Financial Officer 06/13/2024 AP Indirect COM 15,000 $15.51 $232,650.00 25,000
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Filer's Name
Relationship/ Title
Trans.
Date
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Value
Total Shares Owned
Peters John Sheldon Chief Insurance Officer 03/04/2026 DS Direct COM 3,571 $52.50 $187,477.50 76,729 Bixby Timothy E Chief Financial Officer 03/03/2026 DS Direct COM 2,135 $50.12 $107,006.20 249,490 Peters John Sheldon Chief Insurance Officer 03/03/2026 DS Direct COM 1,773 $50.12 $88,862.76 80,300 Prosor Maya Chief Business Officer 03/03/2026 DS Direct COM 223 $50.12 $11,176.76 7,404 Schreiber Daniel A. Chief Executive Officer 01/23/2026 DS Indirect COM 9,108 $99.04 $902,056.32 1,514,426 Schreiber Daniel A. Chief Executive Officer 01/22/2026 DS Indirect COM 126,625 $94.74 $11,996,452.50 1,523,534 Peters John Sheldon Chief Insurance Officer 01/22/2026 DS Direct COM 9,000 $90.00 $810,000.00 70,228 Peters John Sheldon Chief Insurance Officer 01/06/2026 DS Direct COM 10,000 $80.00 $800,000.00 60,771 Eckstein Adina Chief Operating Officer 12/11/2025 DS Direct COM 7,919 $84.15 $666,383.85 188,391 Schwartz Debra Director 12/11/2025 DS Direct COM 4,200 $83.59 $351,078.00 21,567 Peters John Sheldon Chief Insurance Officer 12/10/2025 DS Direct COM 3,554 $81.00 $287,874.00 70,771 Eckstein Adina Chief Operating Officer 12/10/2025 DS Direct COM 7,919 $81.15 $642,626.85 196,310 Eckstein Adina Chief Operating Officer 12/09/2025 DS Direct COM 29,237 $77.17 $2,256,219.29 204,229 Eckstein Adina Chief Operating Officer 12/08/2025 DS Direct COM 7,919 $78.94 $625,125.86 204,229 Eckstein Adina Chief Operating Officer 12/08/2025 DS Direct COM 15,839 $78.92 $1,250,013.88 212,148 Eckstein Adina Chief Operating Officer 12/08/2025 DS Direct COM 17,799 $78.97 $1,405,587.03 227,987 Peters John Sheldon Chief Insurance Officer 12/03/2025 DS Direct COM 2,667 $72.37 $193,010.79 74,325 Bixby Timothy E Chief Financial Officer 12/02/2025 DS Direct COM 2,862 $72.74 $208,181.88 251,625 Peters John Sheldon Chief Insurance Officer 12/02/2025 DS Direct COM 2,677 $72.74 $194,724.98 76,992 Prosor Maya Chief Business Officer 12/02/2025 DS Direct COM 198 $72.74 $14,402.52 7,627 Peters John Sheldon Chief Insurance Officer 11/24/2025 DS Direct COM 3,798 $73.25 $278,203.50 79,669 Peters John Sheldon Chief Insurance Officer 11/20/2025 DS Direct COM 18,930 $72.77 $1,377,536.10 83,467 Bixby Timothy E Chief Financial Officer 11/11/2025 DS Indirect COM 30,000 $75.51 $2,265,300.00 0 Schreiber Daniel A. Chief Executive Officer 11/11/2025 DG Direct COM 35,000 $0.00 $0.00 24,327 Eckstein Adina Chief Operating Officer 11/10/2025 DS Direct COM 5,988 $78.00 $467,064.00 227,987
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Filer's Name
Relationship/ Title
Trans.
Date
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Value
Total Shares Owned
Peters John Sheldon Chief Insurance Officer 02/12/2026 AM Direct COM 11,845 $11.61 $137,520.45 82,073 Peters John Sheldon Chief Insurance Officer 01/08/2026 AM Direct COM 18,457 $5.26 $97,083.82 79,228 Eckstein Adina Chief Operating Officer 12/09/2025 AM Direct COM 29,237 $44.57 $1,303,093.09 233,466 Eckstein Adina Chief Operating Officer 12/08/2025 AM Direct COM 1,549 $44.57 $69,038.93 245,786 Eckstein Adina Chief Operating Officer 12/08/2025 AM Direct COM 16,250 $24.47 $397,637.50 244,237 Eckstein Adina Chief Operating Officer 11/10/2025 AM Direct COM 5,988 $27.35 $163,771.80 233,975 Eckstein Adina Chief Operating Officer 11/07/2025 AM Direct COM 20,000 $27.35 $547,000.00 247,987 Eckstein Adina Chief Operating Officer 11/07/2025 AM Direct COM 20,000 $27.35 $547,000.00 247,987 Eckstein Adina Chief Operating Officer 08/13/2025 AM Direct COM 5,000 $24.47 $122,350.00 189,653 Peters John Sheldon Chief Insurance Officer 08/13/2025 AM Direct COM 38,155 $11.61 $442,979.55 143,270 Eckstein Adina Chief Operating Officer 08/11/2025 AM Direct COM 0 $24.47 $0.00 189,653 Eckstein Adina Chief Operating Officer 08/05/2025 AM Direct COM 3,750 $23.69 $88,837.50 194,653 Eckstein Adina Chief Operating Officer 08/05/2025 AM Direct COM 1,250 $23.69 $29,612.50 190,903 Bixby Timothy E Chief Financial Officer 07/21/2025 AM Direct COM 1,000 $23.69 $23,690.00 264,393 Bixby Timothy E Chief Financial Officer 07/18/2025 AM Direct COM 6,000 $23.69 $142,140.00 269,393 Bixby Timothy E Chief Financial Officer 07/14/2025 AM Direct COM 5,000 $23.69 $118,450.00 268,393 Bixby Timothy E Chief Financial Officer 07/07/2025 AM Direct COM 11,000 $23.69 $260,590.00 274,393 Bixby Timothy E Chief Financial Officer 06/30/2025 AM Direct COM 11,000 $23.69 $260,590.00 274,393 Peters John Sheldon Chief Insurance Officer 06/23/2025 AM Direct COM 6,543 $5.26 $34,416.18 112,658 Bixby Timothy E Chief Financial Officer 06/23/2025 AM Direct COM 11,000 $23.69 $260,590.00 274,393 Eckstein Adina Chief Operating Officer 06/23/2025 AM Direct COM 5,000 $23.69 $118,450.00 194,653 Bixby Timothy E Chief Financial Officer 06/16/2025 AM Direct COM 11,000 $23.69 $260,590.00 274,393 Bixby Timothy E Chief Financial Officer 06/11/2025 AM Direct COM 6,000 $23.69 $142,140.00 269,393 Bixby Timothy E Chief Financial Officer 06/09/2025 AM Direct COM 5,000 $23.69 $118,450.00 268,393 Bixby Timothy E Chief Financial Officer 06/05/2025 AM Direct COM 5,000 $23.69 $118,450.00 268,393
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Transaction Type Key
First letter: A = Acquired, D = Disposed
Second letter:
A = Grant, award or other acquisition pursuant to Rule 16b-3(d)
C = Conversion of derivative security |
D = Disposition to the issuer of issuer equity securities pursuant to Rule 16b-3(e) |
E = Expiration of short derivative position |
F = Payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. |
G = Gift |
H = Expiration (or cancellation) of long derivative position with value received |
I = Discretionary transaction in accordance with Rule 16b-3(f) |
J = Other |
L = Small acquisition under Rule 16a-6 |
M = Exercise or conversion of derivative security exempted pursuant to Rule 16b-3 |
O = Exercise of out-of-the-money derivative security |
P = Open market or private purchase |
S = Open market or private sale |
U = Disposition pursuant to a tender of shares in a change of control transaction |
W = Acquisition or disposition by will or the laws of descent and distribution |
X = Exercise of in-the-money or at-the-money derivative security |
Z = Deposit into or withdrawal from voting trust
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