LMND

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 23

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,437,741

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F24 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $133.01 to $133.98. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 22

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,443,390

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F23 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $132.00 to $132.97. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 21

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,457,489

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F22 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $131.00 to $131.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 20

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,472,029

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F21 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $130.00 to $130.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 19

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,487,304

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F20 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $129.00 to $129.97. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 18

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,508,767

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F19 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $128.00 to $128.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 17

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,536,096

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F18 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $127.00 to $127.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 16

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,578,640

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F17 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $126.00 to $126.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 15

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,601,722

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F16 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $125.35 to $125.98. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 14

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,606,022

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F15 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $124.34 to $124.86. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 13

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,607,222

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F14 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $123.01 to $123.26. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 12

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,608,022

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F13 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $122.38 to $122.80. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 11

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,609,422

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F12 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $119.00 to $119.39. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 10

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,640,067

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F11 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $118.01 to $118.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 9

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,650,450

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F10 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $117.00 to $117.98. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 8

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,659,940

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F9 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $116.01 to $116.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 7

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,666,145

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F8 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $115.02 to $115.88. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 6

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,671,445

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F7 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $114.00 to $114.98. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 5

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,684,754

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F6 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $113.00 to $113.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 4

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,700,138

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $112.00 to $112.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 3

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,719,860

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $111.00 to $111.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 2

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,730,097

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $110.00 to $110.98. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 1

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,737,878

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $109.00 to $109.99. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000037 · wf-form4_160859297537259.xml · nonDerivative · entry 6

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,798,817

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F7 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $104.00 to $104.92. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000037 · wf-form4_160859297537259.xml · nonDerivative · entry 5

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,799,517

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F6 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $103.12 to $103.68. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000037 · wf-form4_160859297537259.xml · nonDerivative · entry 4

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,800,017

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $102.06 to $102.95. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000037 · wf-form4_160859297537259.xml · nonDerivative · entry 3

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,801,589

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $101.28 to $101.81. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000037 · wf-form4_160859297537259.xml · nonDerivative · entry 2

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,801,989

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $100.00 to $100.96. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000037 · wf-form4_160859297537259.xml · nonDerivative · entry 1

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,803,769

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $99.00 to $99.96. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001209191-20-063783 · doc4.xml · nonDerivative · entry 4

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,313

SEC source: 0001209191-20-063783 · doc4.xml · nonDerivative · entry 3

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,413

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $96.00 to $96.30, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001209191-20-063783 · doc4.xml · nonDerivative · entry 2

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 20,413

SEC source: 0001209191-20-063783 · doc4.xml · nonDerivative · entry 1

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 21,313

SEC source: 0001209191-21-025010 · doc4a.xml · nonDerivative · entry 4

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 65,655

F1 · balance_after: The original Form 4, filed on December 16, 2020, is being amended by this Form 4 amendment solely to correct an administrative error, which misreported the starting balance of Mr. Eisenberg's directly held shares. As a result of this administrative error, the number of shares reflected as directly owned by the reporting person following the corrected transaction reflects an increase by 47,342 shares in the number of shares reported.

SEC source: 0001209191-21-025010 · doc4a.xml · nonDerivative · entry 3

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 65,755

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $96.00 to $96.30, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F1 · balance_after: The original Form 4, filed on December 16, 2020, is being amended by this Form 4 amendment solely to correct an administrative error, which misreported the starting balance of Mr. Eisenberg's directly held shares. As a result of this administrative error, the number of shares reflected as directly owned by the reporting person following the corrected transaction reflects an increase by 47,342 shares in the number of shares reported.

SEC source: 0001209191-21-025010 · doc4a.xml · nonDerivative · entry 2

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 67,755

F1 · balance_after: The original Form 4, filed on December 16, 2020, is being amended by this Form 4 amendment solely to correct an administrative error, which misreported the starting balance of Mr. Eisenberg's directly held shares. As a result of this administrative error, the number of shares reflected as directly owned by the reporting person following the corrected transaction reflects an increase by 47,342 shares in the number of shares reported.

SEC source: 0001209191-21-025010 · doc4a.xml · nonDerivative · entry 1

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 68,655

F1 · balance_after: The original Form 4, filed on December 16, 2020, is being amended by this Form 4 amendment solely to correct an administrative error, which misreported the starting balance of Mr. Eisenberg's directly held shares. As a result of this administrative error, the number of shares reflected as directly owned by the reporting person following the corrected transaction reflects an increase by 47,342 shares in the number of shares reported.

SEC source: 0001691421-20-000035 · wf-form4_160799050820455.xml · nonDerivative · entry 14

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,807,918

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F15 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $99.91 to $99.95. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001209191-20-063246 · doc4.xml · nonDerivative · entry 5

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 22,313

SEC source: 0001209191-20-063246 · doc4.xml · nonDerivative · entry 4

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 22,386

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $100.50 to $101.33, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001209191-20-063246 · doc4.xml · nonDerivative · entry 3

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 24,313

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $95.00 to $95.03, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001209191-20-063246 · doc4.xml · nonDerivative · entry 2

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 27,313

SEC source: 0001209191-21-025009 · doc4a.xml · nonDerivative · entry 5

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 68,438

F2 · balance_after: The original Form 4, filed on December 14, 2020, is being amended by this Form 4 amendment solely to correct an administrative error, which misreported the starting balance of Mr. Eisenberg's directly held shares. As a result of this administrative error, the number of shares reflected as directly owned by the reporting person following the corrected transaction reflects an increase by 46,125 shares in the number of shares reported.

SEC source: 0001209191-21-025009 · doc4a.xml · nonDerivative · entry 4

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 68,511

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $100.50 to $101.33, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · balance_after: The original Form 4, filed on December 14, 2020, is being amended by this Form 4 amendment solely to correct an administrative error, which misreported the starting balance of Mr. Eisenberg's directly held shares. As a result of this administrative error, the number of shares reflected as directly owned by the reporting person following the corrected transaction reflects an increase by 46,125 shares in the number of shares reported.

SEC source: 0001209191-21-025009 · doc4a.xml · nonDerivative · entry 3

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 70,438

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $95.00 to $95.03, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · balance_after: The original Form 4, filed on December 14, 2020, is being amended by this Form 4 amendment solely to correct an administrative error, which misreported the starting balance of Mr. Eisenberg's directly held shares. As a result of this administrative error, the number of shares reflected as directly owned by the reporting person following the corrected transaction reflects an increase by 46,125 shares in the number of shares reported.

SEC source: 0001209191-21-025009 · doc4a.xml · nonDerivative · entry 2

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 73,438

F2 · balance_after: The original Form 4, filed on December 14, 2020, is being amended by this Form 4 amendment solely to correct an administrative error, which misreported the starting balance of Mr. Eisenberg's directly held shares. As a result of this administrative error, the number of shares reflected as directly owned by the reporting person following the corrected transaction reflects an increase by 46,125 shares in the number of shares reported.

SEC source: 0001691421-20-000035 · wf-form4_160799050820455.xml · nonDerivative · entry 13

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,808,031

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F14 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $111.10 to $111.51. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000035 · wf-form4_160799050820455.xml · nonDerivative · entry 12

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,808,731

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F13 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $110.01 to $110.84. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000035 · wf-form4_160799050820455.xml · nonDerivative · entry 11

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,815,884

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F12 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $109.00 to $109.91. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001691421-20-000035 · wf-form4_160799050820455.xml · nonDerivative · entry 10

Wininger Shai · CIK 0001803365 · Director · See Remarks · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,828,373

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

F11 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $108.20 to $108.98. The reporting person undertakes to provide Lemonade, Inc. (the "Company"), any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.