LMND

SEC source: 0001691421-21-000087 · wf-form4_163598282982995.xml · nonDerivative · entry 2

BIXBY TIMOTHY E · CIK 0001232142 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 215,000

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

SEC source: 0001691421-21-000089 · wf-form4_163614911890038.xml · derivative · entry 3

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 73,250

Underlying: COMMON STOCK · 500 shares

Expires 2027-03-07

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: The stock option is fully vested.

SEC source: 0001691421-21-000089 · wf-form4_163614911890038.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,537

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

SEC source: 0001691421-21-000089 · wf-form4_163614911890038.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,037

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001691421-21-000087 · wf-form4_163598282982995.xml · nonDerivative · entry 1

BIXBY TIMOTHY E · CIK 0001232142 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 220,000

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

SEC source: 0001691421-21-000085 · wf-form4_163477379337797.xml · nonDerivative · entry 1

BIXBY TIMOTHY E · CIK 0001232142 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 225,000

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

SEC source: 0001209191-21-055669 · doc4.xml · nonDerivative · entry 2

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 118,163

SEC source: 0001209191-21-055669 · doc4.xml · nonDerivative · entry 1

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 120,163

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $76.11 to $76.94, 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: 0001691421-21-000083 · wf-form4_163071086954772.xml · derivative · entry 4

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 73,750

Underlying: COMMON STOCK · 500 shares

Expires 2027-03-07

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: The stock option is fully vested.

SEC source: 0001691421-21-000083 · wf-form4_163071086954772.xml · nonDerivative · entry 3

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,537

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

SEC source: 0001691421-21-000083 · wf-form4_163071086954772.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,787

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

SEC source: 0001691421-21-000083 · wf-form4_163071086954772.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,037

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001691421-21-000079 · wf-form4_162812008829466.xml · derivative · entry 5

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 74,250

Underlying: COMMON STOCK · 750 shares

Expires 2027-03-07

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_date: The stock option is fully vested.

SEC source: 0001691421-21-000079 · wf-form4_162812008829466.xml · nonDerivative · entry 4

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,537

F2 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

SEC source: 0001691421-21-000079 · wf-form4_162812008829466.xml · nonDerivative · entry 3

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,787

F2 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan.

SEC source: 0001691421-21-000079 · wf-form4_162812008829466.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,287

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001874702-21-000004 · wf-form4_162707843548006.xml · derivative · entry 2

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,000

Underlying: COMMON STOCK · 10,000 shares

Expires 2031-07-21

F2 · derivative.exercise_date: The option will vest and become exercisable in 16 equal quarterly installments beginning on October 21, 2021, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date.

SEC source: 0001874702-21-000004 · wf-form4_162707843548006.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 30,000

F1 · kind: Represents an award of restricted stock units, which will vest in 16 equal quarterly installments beginning on October 21, 2021, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

SEC source: 0001691421-21-000069 · wf-form4_162371713598952.xml · nonDerivative · entry 1

Martincevic Silvija · CIK 0001834580 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,377

F1 · shares: Represents an award of restricted stock units, which will vest and become exerciseable on the earlier of (i) the day immediately preceding the date of the first annual meeting following the date of the grant and (ii) June 9, 2022. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

SEC source: 0001691421-21-000067 · wf-form4_162371696154141.xml · nonDerivative · entry 1

Novoselsky Irina · CIK 0001858550 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,377

F1 · shares: Represents an award of restricted stock units, which will vest and become exerciseable on the earlier of (i) the day immediately preceding the date of the first annual meeting following the date of the grant and (ii) June 9, 2022. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

SEC source: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 10

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 51,120

F9 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $106.92 to $107.50, 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: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 9

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 52,120

F8 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $105.70 to $106.50, 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: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 8

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 53,620

F7 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $104.09 to $104.92, 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: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 7

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 55,120

F6 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $103.03 to $104.00, 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: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 6

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,120

SEC source: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 5

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 59,120

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $99.90 to $100.50, 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: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 4

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 61,120

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $98.58 to $98.90, 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: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 3

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 62,002

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $97.56 to $98.50, 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: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 2

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 64,620

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $96.40 to $97.10, 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: 0001209191-21-039166 · doc4.xml · nonDerivative · entry 1

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 66,620

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $95.20 to $96.10, 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: 0001062993-21-005397 · form4.xml · nonDerivative · entry 6

Cutler Joel E · CIK 0001337122 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Directly held by General Catalyst Group VIII Supplemental, L.P.

Disclosed balance after: 808,754

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $97.64 to $98.04, inclusive.

F2 · ownership.nature: General Catalyst GP VIII, LLC ("GC VIII LLC") is the general partner of General Catalyst Partners VIII, L.P., which is the general partner of General Catalyst Group VIII, L.P. ("GC Group VIII") and General Catalyst Group VIII Supplemental, L.P. ("GC Group VIII Supplemental"). General Catalyst Group Management, LLC ("GCGM") is the manager of GC VIII LLC. General Catalyst Group Management Holdings, L.P. ("GCGMH") is the manager of GCGM. General Catalyst Group Management Holdings GP, LLC ("GCGMH LLC") is the general partner of GCGMH. Each of Kenneth Chenault, Joel Cutler, David Fialkow, and Hemant Taneja is a managing director of GCGMH LLC and shares voting and investment power over the shares held by GC Group VIII and GC Group VIII Supplemental. However, the reporting person disclaims beneficial ownership over such shares except to the extent of his pecuniary interest therein, if any.

SEC source: 0001062993-21-005397 · form4.xml · nonDerivative · entry 5

Cutler Joel E · CIK 0001337122 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Directly held by General Catalyst Group VIII Supplemental, L.P.

Disclosed balance after: 862,537

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $96.68 to $97.63, inclusive.

F2 · ownership.nature: General Catalyst GP VIII, LLC ("GC VIII LLC") is the general partner of General Catalyst Partners VIII, L.P., which is the general partner of General Catalyst Group VIII, L.P. ("GC Group VIII") and General Catalyst Group VIII Supplemental, L.P. ("GC Group VIII Supplemental"). General Catalyst Group Management, LLC ("GCGM") is the manager of GC VIII LLC. General Catalyst Group Management Holdings, L.P. ("GCGMH") is the manager of GCGM. General Catalyst Group Management Holdings GP, LLC ("GCGMH LLC") is the general partner of GCGMH. Each of Kenneth Chenault, Joel Cutler, David Fialkow, and Hemant Taneja is a managing director of GCGMH LLC and shares voting and investment power over the shares held by GC Group VIII and GC Group VIII Supplemental. However, the reporting person disclaims beneficial ownership over such shares except to the extent of his pecuniary interest therein, if any.

SEC source: 0001062993-21-005397 · form4.xml · nonDerivative · entry 4

Cutler Joel E · CIK 0001337122 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Directly held by General Catalyst Group VIII Supplemental, L.P.

Disclosed balance after: 1,102,430

F1 · price: The price reported in Column 4 is a weighted average price. The shares were sold in multiple transactions at prices ranging from $95.72 to $96.68, inclusive. The Reporting Person undertakes to provide the Issuer, any security holder, 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 ranges set forth in this footnote and in footnotes (3) through (4) of this Form 4.

F2 · ownership.nature: General Catalyst GP VIII, LLC ("GC VIII LLC") is the general partner of General Catalyst Partners VIII, L.P., which is the general partner of General Catalyst Group VIII, L.P. ("GC Group VIII") and General Catalyst Group VIII Supplemental, L.P. ("GC Group VIII Supplemental"). General Catalyst Group Management, LLC ("GCGM") is the manager of GC VIII LLC. General Catalyst Group Management Holdings, L.P. ("GCGMH") is the manager of GCGM. General Catalyst Group Management Holdings GP, LLC ("GCGMH LLC") is the general partner of GCGMH. Each of Kenneth Chenault, Joel Cutler, David Fialkow, and Hemant Taneja is a managing director of GCGMH LLC and shares voting and investment power over the shares held by GC Group VIII and GC Group VIII Supplemental. However, the reporting person disclaims beneficial ownership over such shares except to the extent of his pecuniary interest therein, if any.

SEC source: 0001062993-21-005397 · form4.xml · nonDerivative · entry 3

Cutler Joel E · CIK 0001337122 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Directly held by General Catalyst Group VIII, L.P.

Disclosed balance after: 697,968

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $97.64 to $98.04, inclusive.

F2 · ownership.nature: General Catalyst GP VIII, LLC ("GC VIII LLC") is the general partner of General Catalyst Partners VIII, L.P., which is the general partner of General Catalyst Group VIII, L.P. ("GC Group VIII") and General Catalyst Group VIII Supplemental, L.P. ("GC Group VIII Supplemental"). General Catalyst Group Management, LLC ("GCGM") is the manager of GC VIII LLC. General Catalyst Group Management Holdings, L.P. ("GCGMH") is the manager of GCGM. General Catalyst Group Management Holdings GP, LLC ("GCGMH LLC") is the general partner of GCGMH. Each of Kenneth Chenault, Joel Cutler, David Fialkow, and Hemant Taneja is a managing director of GCGMH LLC and shares voting and investment power over the shares held by GC Group VIII and GC Group VIII Supplemental. However, the reporting person disclaims beneficial ownership over such shares except to the extent of his pecuniary interest therein, if any.

SEC source: 0001062993-21-005397 · form4.xml · nonDerivative · entry 2

Cutler Joel E · CIK 0001337122 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Directly held by General Catalyst Group VIII, L.P.

Disclosed balance after: 744,384

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $96.68 to $97.63, inclusive.

F2 · ownership.nature: General Catalyst GP VIII, LLC ("GC VIII LLC") is the general partner of General Catalyst Partners VIII, L.P., which is the general partner of General Catalyst Group VIII, L.P. ("GC Group VIII") and General Catalyst Group VIII Supplemental, L.P. ("GC Group VIII Supplemental"). General Catalyst Group Management, LLC ("GCGM") is the manager of GC VIII LLC. General Catalyst Group Management Holdings, L.P. ("GCGMH") is the manager of GCGM. General Catalyst Group Management Holdings GP, LLC ("GCGMH LLC") is the general partner of GCGMH. Each of Kenneth Chenault, Joel Cutler, David Fialkow, and Hemant Taneja is a managing director of GCGMH LLC and shares voting and investment power over the shares held by GC Group VIII and GC Group VIII Supplemental. However, the reporting person disclaims beneficial ownership over such shares except to the extent of his pecuniary interest therein, if any.

SEC source: 0001062993-21-005397 · form4.xml · nonDerivative · entry 1

Cutler Joel E · CIK 0001337122 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Directly held by General Catalyst Group VIII, L.P.

Disclosed balance after: 951,415

F1 · price: The price reported in Column 4 is a weighted average price. The shares were sold in multiple transactions at prices ranging from $95.72 to $96.68, inclusive. The Reporting Person undertakes to provide the Issuer, any security holder, 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 ranges set forth in this footnote and in footnotes (3) through (4) of this Form 4.

F2 · ownership.nature: General Catalyst GP VIII, LLC ("GC VIII LLC") is the general partner of General Catalyst Partners VIII, L.P., which is the general partner of General Catalyst Group VIII, L.P. ("GC Group VIII") and General Catalyst Group VIII Supplemental, L.P. ("GC Group VIII Supplemental"). General Catalyst Group Management, LLC ("GCGM") is the manager of GC VIII LLC. General Catalyst Group Management Holdings, L.P. ("GCGMH") is the manager of GCGM. General Catalyst Group Management Holdings GP, LLC ("GCGMH LLC") is the general partner of GCGMH. Each of Kenneth Chenault, Joel Cutler, David Fialkow, and Hemant Taneja is a managing director of GCGMH LLC and shares voting and investment power over the shares held by GC Group VIII and GC Group VIII Supplemental. However, the reporting person disclaims beneficial ownership over such shares except to the extent of his pecuniary interest therein, if any.

SEC source: 0001209191-21-037137 · doc4.xml · nonDerivative · entry 1

Eisenberg Michael A · CIK 0001295751 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 71,120

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $90.00 to $90.58, 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: 0001691421-21-000079 · wf-form4_162812008829466.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,537

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

SEC source: 0001691421-21-000042 · wf-form4_161921740354833.xml · derivative · entry 1

Schreiber Daniel A. · CIK 0001815651 · Director · Co-Founder & CEO · 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: 0001691421-21-000048 · wf-form4_161921844806572.xml · nonDerivative · entry 1

Novoselsky Irina · CIK 0001858550 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,950

F1 · kind: Represents an award of restricted stock units, which will vest in three equal annual installments. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

SEC source: 0001691421-21-000046 · wf-form4_161921807626333.xml · nonDerivative · entry 1

Martincevic Silvija · CIK 0001834580 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,950

F1 · shares: Represents an award of restricted stock units, which will vest in three equal annual installments. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

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: 0001691421-21-000034 · wf-form4_161886667498633.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,537

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

SEC source: 0001691421-21-000032 · wf-form4_161603126908159.xml · derivative · entry 3

Seidman Becker Caryn · CIK 0001466453 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 125,000

Underlying: COMMON STOCK · 25,000 shares

Expires 2028-07-11

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: The option is vested and exercisable as to 93,750 shares (including the 25,000 shares disposed of in this exercise) and the remaining shares will vest and become exercisable in six quarterly installments beginning on April 12, 2021.

SEC source: 0001691421-21-000032 · wf-form4_161603126908159.xml · nonDerivative · entry 2

Seidman Becker Caryn · CIK 0001466453 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $106.63 to $107.26. 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: 0001691421-21-000032 · wf-form4_161603126908159.xml · nonDerivative · entry 1

Seidman Becker Caryn · CIK 0001466453 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 25,000

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001691421-21-000030 · wf-form4_161602344049694.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,037

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

SEC source: 0001691421-21-000028 · wf-form4_161559464437036.xml · derivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,000

Underlying: COMMON STOCK · 10,000 shares

Expires 2031-03-10

F1 · derivative.exercise_date: The option will vest and become exercisable in 16 equal quarterly installments beginning on June 10, 2021.

SEC source: 0001062993-21-002682 · form4.xml · nonDerivative · entry 3

SADGER HAIM · CIK 0001207461 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 348,675

F4 · kind: Represents the receipt of shares of Common Stock of the Issuer by virtue of the pro rata in-kind distributions described in footnote (1) above.

F4 · price: Represents the receipt of shares of Common Stock of the Issuer by virtue of the pro rata in-kind distributions described in footnote (1) above.

SEC source: 0001062993-21-002682 · form4.xml · nonDerivative · entry 2

SADGER HAIM · CIK 0001207461 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By estate planning vehicle

Disclosed balance after: 38,013

F4 · kind: Represents the receipt of shares of Common Stock of the Issuer by virtue of the pro rata in-kind distributions described in footnote (1) above.

F4 · price: Represents the receipt of shares of Common Stock of the Issuer by virtue of the pro rata in-kind distributions described in footnote (1) above.