Insider Transactions last 24 months for Lemonade, Inc. - NYSE: LMND
Transactions
All
Buy
Sell
Option Exercise
Filer's Name
Relationship/
Trans.
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Total Shares Owned
Eisenberg Michael A Director 09/12/2025 DG Direct COM 4,000 $0.00 $0.00 200,452 Bixby Timothy E Chief Financial Officer 09/03/2025 DS Direct COM 2,906 $50.34 $146,288.04 260,487 Peters John Sheldon Chief Insurance Officer 09/03/2025 DS Direct COM 2,718 $50.34 $136,824.12 102,397 Prosor Maya Chief Business Officer 09/03/2025 DS Direct COM 282 $50.34 $14,195.88 7,825 Eckstein Adina Chief Operating Officer 08/21/2025 AA Direct COM 38,334 $0.00 $0.00 227,987 Eckstein Adina Chief Operating Officer 08/13/2025 DS Direct COM 5,000 $58.00 $290,000.00 189,653 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 DS Direct COM 38,155 $60.00 $2,289,300.00 105,115 Peters John Sheldon Chief Insurance Officer 08/13/2025 AM Direct COM 38,155 $11.61 $442,979.55 143,270 Peters John Sheldon Chief Insurance Officer 08/12/2025 DG Direct COM 1,000 $0.00 $0.00 105,115 Eckstein Adina Chief Operating Officer 08/11/2025 DS Direct COM 0 $53.00 $0.00 189,653 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 DS Direct COM 5,000 $49.00 $245,000.00 189,653 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 DS Direct COM 1,000 $42.70 $42,700.00 263,393 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 DS Direct COM 6,000 $42.50 $255,000.00 263,393 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 DS Direct COM 5,000 $38.16 $190,800.00 263,393 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 DS Direct COM 6,000 $42.50 $255,000.00 263,393 Bixby Timothy E Chief Financial Officer 07/07/2025 DS Direct COM 5,000 $42.28 $211,400.00 269,393 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 DS Direct COM 11,000 $42.69 $469,590.00 263,393
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Filer's Name
Relationship/
Trans.
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Total Shares Owned
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 Bixby Timothy E Chief Financial Officer 03/06/2024 AP Indirect COM 10,000 $16.54 $165,400.00 10,000 Prosor Maya Chief Business Officer 03/01/2024 AA Direct COM 7,576 $0.00 $0.00 9,812 Peters John Sheldon Chief Insurance Officer 03/01/2024 AA Direct COM 4,025 $0.00 $0.00 77,509 Bixby Timothy E Chief Financial Officer 03/01/2024 AA Direct COM 12,973 $0.00 $0.00 281,554 Wininger Shai President 02/02/2024 AA Direct COM 9,327 $0.00 $0.00 3,392,986 Eckstein Adina Chief Operating Officer 02/02/2024 AA Direct COM 7,486 $0.00 $0.00 135,986 Schreiber Daniel A. Chief Executive Officer 02/02/2024 AA Direct COM 9,327 $0.00 $0.00 59,327 Schwartz Debra Director 11/21/2023 AA Direct COM 10,924 $0.00 $0.00 12,352 Haj-Yehia Samer Director 11/21/2023 AA Direct COM 10,924 $0.00 $0.00 10,924
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Filer's Name
Relationship/
Trans.
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Total Shares Owned
Eisenberg Michael A Director 09/12/2025 DG Direct COM 4,000 $0.00 $0.00 200,452 Bixby Timothy E Chief Financial Officer 09/03/2025 DS Direct COM 2,906 $50.34 $146,288.04 260,487 Peters John Sheldon Chief Insurance Officer 09/03/2025 DS Direct COM 2,718 $50.34 $136,824.12 102,397 Prosor Maya Chief Business Officer 09/03/2025 DS Direct COM 282 $50.34 $14,195.88 7,825 Eckstein Adina Chief Operating Officer 08/13/2025 DS Direct COM 5,000 $58.00 $290,000.00 189,653 Peters John Sheldon Chief Insurance Officer 08/13/2025 DS Direct COM 38,155 $60.00 $2,289,300.00 105,115 Peters John Sheldon Chief Insurance Officer 08/12/2025 DG Direct COM 1,000 $0.00 $0.00 105,115 Eckstein Adina Chief Operating Officer 08/11/2025 DS Direct COM 0 $53.00 $0.00 189,653 Eckstein Adina Chief Operating Officer 08/05/2025 DS Direct COM 5,000 $49.00 $245,000.00 189,653 Bixby Timothy E Chief Financial Officer 07/21/2025 DS Direct COM 1,000 $42.70 $42,700.00 263,393 Bixby Timothy E Chief Financial Officer 07/18/2025 DS Direct COM 6,000 $42.50 $255,000.00 263,393 Bixby Timothy E Chief Financial Officer 07/14/2025 DS Direct COM 5,000 $38.16 $190,800.00 263,393 Bixby Timothy E Chief Financial Officer 07/07/2025 DS Direct COM 6,000 $42.50 $255,000.00 263,393 Bixby Timothy E Chief Financial Officer 07/07/2025 DS Direct COM 5,000 $42.28 $211,400.00 269,393 Bixby Timothy E Chief Financial Officer 06/30/2025 DS Direct COM 11,000 $42.69 $469,590.00 263,393 Peters John Sheldon Chief Insurance Officer 06/23/2025 DS Direct COM 6,543 $45.00 $294,435.00 106,115 Bixby Timothy E Chief Financial Officer 06/23/2025 DS Direct COM 11,000 $43.36 $476,960.00 263,393 Eckstein Adina Chief Operating Officer 06/23/2025 DS Direct COM 5,000 $45.00 $225,000.00 189,653 Bixby Timothy E Chief Financial Officer 06/16/2025 DS Direct COM 6,000 $42.50 $255,000.00 263,393 Bixby Timothy E Chief Financial Officer 06/16/2025 DS Direct COM 5,000 $41.06 $205,300.00 269,393 Bixby Timothy E Chief Financial Officer 06/11/2025 DS Direct COM 6,000 $42.50 $255,000.00 263,393 Bixby Timothy E Chief Financial Officer 06/09/2025 DS Direct COM 5,000 $40.30 $201,500.00 263,393 Bixby Timothy E Chief Financial Officer 06/05/2025 DS Direct COM 5,000 $37.50 $187,500.00 263,393 Prosor Maya Chief Business Officer 06/03/2025 DS Direct COM 252 $35.25 $8,883.00 8,107 Bixby Timothy E Chief Financial Officer 06/03/2025 DS Direct COM 1,916 $35.25 $67,539.00 263,393
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Filer's Name
Relationship/
Trans.
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Total Shares Owned
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 Peters John Sheldon Chief Insurance Officer 04/02/2025 AM Direct COM 20,000 $2.65 $53,000.00 107,609 Bixby Timothy E Chief Financial Officer 03/24/2025 AM Direct COM 5,000 $23.69 $118,450.00 270,309 Peters John Sheldon Chief Insurance Officer 01/02/2025 AM Direct COM 10,000 $2.65 $26,500.00 89,508 Peters John Sheldon Chief Insurance Officer 12/31/2024 AM Direct COM 10,000 $2.65 $26,500.00 79,508 Peters John Sheldon Chief Insurance Officer 12/30/2024 AM Direct COM 10,000 $5.26 $52,600.00 98,493 Eckstein Adina Chief Operating Officer 11/21/2024 AM Direct COM 6,875 $23.69 $162,868.75 213,297 Eckstein Adina Chief Operating Officer 11/21/2024 AM Direct COM 1,769 $27.35 $48,382.15 206,422 Eckstein Adina Chief Operating Officer 11/21/2024 AM Direct COM 15,000 $24.47 $367,050.00 204,653
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Transaction Type Key A = Acquired, D = Disposed 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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