Wininger Shai

SEC source: 0001803365-26-000004 · wk-form4_1788548756.xml · nonDerivative · entry 1

Wininger Shai · CIK 0001803365 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,416,873

F1 · kind: This transaction represents a gift to a third party. No value was received for the gifted shares.

SEC source: 0001803365-26-000002 · wk-form4_1774037131.xml · nonDerivative · entry 2

Wininger Shai · CIK 0001803365 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,418,749

F2 · shares: Represents an award of performance restricted stock units, which will vest if and only if the Company's stock price sustains a closing price of $110 for at least 30 consecutive trading days within 24 months of the Grant Date.

SEC source: 0001803365-26-000002 · wk-form4_1774037131.xml · nonDerivative · entry 1

Wininger Shai · CIK 0001803365 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,238,749

F1 · shares: Represents an award of restricted stock units ("RSUs"), which will vest in quarterly installments over 8 years, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date. The RSU begins vesting quarterly on June 1, 2026 with 5% of the award vesting during the first year, 10% during the second year, 15% during the third year, 20% during each of the fourth and fifth years, 15% during the sixth year, 10% during the seventh year and 5% during the eighth year. Each RSU represents a contingent right to receive one share of the Issuer's common stock.

SEC source: 0001803365-25-000003 · wk-form4_1756161055.xml · derivative · entry 1

Wininger Shai · CIK 0001803365 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,780

Underlying: COMMON STOCK · 127,780 shares

Expires 2035-08-18

F1 · derivative.exercise_date: The option will vest and become exercisable in 12 equal quarterly installments beginning on August 18, 2025, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date.

SEC source: 0001691421-24-000111 · wk-form4_1723684966.xml · derivative · entry 1

Wininger Shai · CIK 0001803365 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 167,130

Underlying: COMMON STOCK · 167,130 shares

Expires 2034-08-12

F1 · derivative.exercise_date: The option will vest and become exercisable in 12 equal quarterly installments beginning on August 1, 2024, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date.

SEC source: 0001691421-24-000087 · wk-form4_1719442261.xml · derivative · entry 1

Wininger Shai · CIK 0001803365 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 133,572

Underlying: COMMON STOCK · 133,572 shares

Expires 2034-06-23

F1 · derivative.exercise_date: The option will vest and become exercisable in 12 equal quarterly installments beginning on September 23, 2024, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date.

SEC source: 0001691421-24-000010 · wk-form4_1707258226.xml · nonDerivative · entry 1

Wininger Shai · CIK 0001803365 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,392,986

F1 · kind: Represents an award of restricted stock units, which vest in 16 equal quarterly installments beginning on March 1, 2024, subject to the Reporting Person's continuous employment with the Issuer through each vesting date. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

SEC source: 0001691421-23-000099 · wf-form4_169213646034267.xml · derivative · entry 1

Wininger Shai · CIK 0001803365 · Director · Co-Chief Executive Officer · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 117,200

Underlying: COMMON STOCK · 117,200 shares

Expires 2033-08-11

F1 · derivative.exercise_date: The option will vest and become exercisable in 16 equal quarterly installments beginning on November 7, 2023.

SEC source: 0001691421-22-000059 · wf-form4_166078776285135.xml · derivative · entry 1

Wininger Shai · CIK 0001803365 · Director · Co-Chief Executive Officer · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 500,000

Underlying: COMMON STOCK · 500,000 shares

Expires 2032-08-15

F1 · derivative.exercise_date: The option will vest and become exercisable in 16 equal quarterly installments beginning on November 15, 2022.

SEC source: 0001691421-21-000044 · wf-form4_161921773133578.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 600,000

Underlying: COMMON STOCK · 600,000 shares

Expires not disclosed

F1 · derivative.exercise_date: The stock option vests in 16 equal quarterly installments, and will become exercisable, if at all, in four equal increments if the average daily closing price of the Issuer's common stock on the New York Stock Exchange during any 30 consecutive calendar day period exceeds $126, $162, $198 and $234, respectively.

F1 · derivative.expiration_date: The stock option vests in 16 equal quarterly installments, and will become exercisable, if at all, in four equal increments if the average daily closing price of the Issuer's common stock on the New York Stock Exchange during any 30 consecutive calendar day period exceeds $126, $162, $198 and $234, respectively.

SEC source: 0001691421-21-000008 · wf-form4_161127333569737.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Indirect · By spouse

Disclosed balance after: 5,000

Underlying: COMMON STOCK · 5,000 shares

Expires 2031-01-19

F1 · derivative.exercise_date: The option will vest and become exercisable in 16 equal quarterly installments beginning on April 19, 2021.

SEC source: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 10

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,383,659

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 $131.00 to $131.01. 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: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 9

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,383,759

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 $130.03 to $130.40. 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: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 8

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,384,059

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 $129.01 to $129.92. 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: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 7

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,386,248

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 $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: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 6

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,388,054

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 $127.04 to $127.94. 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: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 5

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,389,506

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 $126.00 to $126.97. 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: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 4

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,392,204

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 $125.00 to $125.96. 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: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 3

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,401,887

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 $124.01 to $124.97. 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: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,407,893

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 $123.00 to $123.90. 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: 0001691421-20-000042 · wf-form4_160920226642203.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,409,222

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

SEC source: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 26

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,409,422

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

F27 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $136.01 to $136.95. 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: 0001691421-20-000039 · wf-form4_160877576545268.xml · nonDerivative · entry 25

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,412,199

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

F26 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $135.00 to $135.98. 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 24

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,425,344

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

F25 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $134.00 to $134.98. 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 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.