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Peters John Sheldon

Disclosed activity across 1 company

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22901
SEC CIK
0001816299

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
Lemonade, Inc.LMND · Entity 4057Chief Insurance OfficerSeptember 03, 2026September 08, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

Lemonade, Inc.

Report date September 03, 2026 · Filed September 08, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
COMMON STOCKSEC Table I · non-derivativeDirect73,834 Ending reported balance After 2026-09-04 transaction · row 2
2 source rows · reconciled sequence

Row 1 · 2026-09-03 · Sale · Disposed 859 · Balance 76,083

F1: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

Row 2 · 2026-09-04 · Sale · Disposed 2,249 · Balance 73,834

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

Filing footnotes · ownership attribution and instrument terms

F1: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

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

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
September 04, 2026 Filed Sep 8, 2026 21:33 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 2,249 $54.45 $122,458.05
Disclosure

SEC source: 0001816299-26-000023 · wk-form4_1788903193.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 73,834

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

Read SEC document
September 03, 2026 Filed Sep 8, 2026 21:33 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 859 $54.63 $46,927.17
Disclosure

SEC source: 0001816299-26-000023 · wk-form4_1788903193.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 76,083

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

Read SEC document
August 13, 2026 Filed Aug 17, 2026 21:05 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 11,000 $52.55 $578,050.00
Disclosure

SEC source: 0001816299-26-000021 · wk-form4_1787000748.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 76,942

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions. 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.

Read SEC document
July 27, 2026 Filed Jul 29, 2026 22:47 UTC Lemonade, Inc. LMND · Entity 4057 GrantCOMMON STOCK 10,000 $0.00 $0.00
Disclosure

SEC source: 0001816299-26-000019 · wk-form4_1785365232.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 87,942

F1 · shares: Represents an award of restricted stock units, which will vest in 16 equal quarterly installments beginning on September 1, 2026, 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.

Read SEC document
July 06, 2026 Filed Jul 9, 2026 01:40 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 3,444 $79.00 $272,076.00
Disclosure

SEC source: 0001816299-26-000016 · wk-form4_1783561243.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 77,942

F1 · shares: Represents sale pursuant to a Rule 10b5-1 trading plan, adopted on March 11, 2026.

Read SEC document
June 04, 2026 Filed Jun 5, 2026 21:33 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 3,608 $52.94 $191,007.52
Disclosure

SEC source: 0001816299-26-000014 · wk-form4_1780695226.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 81,386

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

Read SEC document
June 03, 2026 Filed Jun 5, 2026 21:33 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 1,735 $53.17 $92,249.95
Disclosure

SEC source: 0001816299-26-000014 · wk-form4_1780695226.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 84,994

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

Read SEC document
March 04, 2026 Filed Mar 5, 2026 22:53 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 3,571 $52.50 $187,477.50
Disclosure

SEC source: 0001816299-26-000012 · wk-form4_1772751197.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 76,729

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

Read SEC document
March 03, 2026 Filed Mar 5, 2026 22:53 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 1,773 $50.12 $88,862.76
Disclosure

SEC source: 0001816299-26-000012 · wk-form4_1772751197.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 80,300

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

Read SEC document
February 12, 2026 Filed Feb 17, 2026 23:11 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 11,845 $11.61 Strike: $11.61 $137,520.45
Disclosure

SEC source: 0001816299-26-000009 · wk-form4_1771369863.xml · derivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: COMMON STOCK · 11,845 shares

Expires 2029-02-05

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.

F1 · derivative.exercise_date: The option is fully vested and exercisable.

Read SEC document
February 12, 2026 Filed Feb 17, 2026 23:11 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 11,845 $11.61 $137,520.45
Disclosure

SEC source: 0001816299-26-000009 · wk-form4_1771369863.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 82,073

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.

Read SEC document
January 22, 2026 Filed Jan 23, 2026 21:13 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 9,000 $90.00 $810,000.00
Disclosure

SEC source: 0001816299-26-000007 · wk-form4_1769202831.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 70,228

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan, adopted August 22, 2025.

Read SEC document
January 08, 2026 Filed Jan 13, 2026 19:22 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 18,457 $5.26 Strike: $5.26 $97,083.82
Disclosure

SEC source: 0001816299-26-000005 · wk-form4_1768332148.xml · derivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,000

Underlying: COMMON STOCK · 18,457 shares

Expires 2028-03-27

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.

F1 · derivative.exercise_date: The option is fully vested and exercisable.

Read SEC document
January 08, 2026 Filed Jan 13, 2026 19:22 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 18,457 $5.26 $97,083.82
Disclosure

SEC source: 0001816299-26-000005 · wk-form4_1768332148.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 79,228

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.

Read SEC document
January 06, 2026 Filed Jan 8, 2026 21:36 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 10,000 $80.00 $800,000.00
Disclosure

SEC source: 0001816299-26-000003 · wk-form4_1767908212.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 60,771

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan, adopted August 22, 2025.

Read SEC document
December 10, 2025 Filed Dec 11, 2025 22:11 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 3,554 $81.00 $287,874.00
Disclosure

SEC source: 0001816299-25-000018 · wk-form4_1765491104.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 70,771

Read SEC document
December 03, 2025 Filed Dec 4, 2025 21:49 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 2,667 $72.37 $193,010.79
Disclosure

SEC source: 0001816299-25-000014 · wk-form4_1764884970.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 74,325

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

Read SEC document
December 02, 2025 Filed Dec 4, 2025 21:49 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 2,677 $72.74 $194,724.98
Disclosure

SEC source: 0001816299-25-000014 · wk-form4_1764884970.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 76,992

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

Read SEC document
November 24, 2025 Filed Nov 24, 2025 22:31 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 3,798 $73.25 $278,203.50
Disclosure

SEC source: 0001816299-25-000012 · wk-form4_1764023480.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 79,669

Read SEC document
November 20, 2025 Filed Nov 24, 2025 22:31 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 18,930 $72.77 $1,377,536.10
Disclosure

SEC source: 0001816299-25-000012 · wk-form4_1764023480.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 83,467

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan, adopted August 22, 2025.

Read SEC document
September 03, 2025 Filed Sep 5, 2025 22:49 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 2,718 $50.34 $136,824.12
Disclosure

SEC source: 0001816299-25-000010 · wk-form4_1757112567.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 102,397

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

Read SEC document
August 21, 2025 Filed Aug 25, 2025 22:15 UTC Lemonade, Inc. LMND · Entity 4057 GrantSTOCK OPTION · Derivative 25,556 $0.00 Strike: $59.74 $0.00
Disclosure

SEC source: 0001816299-25-000008 · wk-form4_1756160114.xml · derivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,556

Underlying: COMMON STOCK · 25,556 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.

Read SEC document
August 13, 2025 Filed Aug 15, 2025 20:12 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 38,155 $11.61 Strike: $11.61 $442,979.55
Disclosure

SEC source: 0001816299-25-000006 · wk-form4_1755288754.xml · derivative · entry 4

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,845

Underlying: COMMON STOCK · 38,155 shares

Expires 2029-02-05

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.

Read SEC document
August 13, 2025 Filed Aug 15, 2025 20:12 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 38,155 $60.00 $2,289,300.00
Disclosure

SEC source: 0001816299-25-000006 · wk-form4_1755288754.xml · nonDerivative · entry 3

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 105,115

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

Read SEC document
August 13, 2025 Filed Aug 15, 2025 20:12 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 38,155 $11.61 $442,979.55
Disclosure

SEC source: 0001816299-25-000006 · wk-form4_1755288754.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 143,270

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.

Read SEC document
August 12, 2025 Filed Aug 15, 2025 20:12 UTC Lemonade, Inc. LMND · Entity 4057 GiftCOMMON STOCK 1,000 $0.00 $0.00
Disclosure

SEC source: 0001816299-25-000006 · wk-form4_1755288754.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 105,115

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

Read SEC document
June 23, 2025 Filed Jun 25, 2025 15:56 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 6,543 $5.26 Strike: $5.26 $34,416.18
Disclosure

SEC source: 0001691421-25-000099 · wk-form4_1750866966.xml · derivative · entry 3

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 28,457

Underlying: COMMON STOCK · 6,543 shares

Expires 2028-03-27

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.

Read SEC document
June 23, 2025 Filed Jun 25, 2025 15:56 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 6,543 $45.00 $294,435.00
Disclosure

SEC source: 0001691421-25-000099 · wk-form4_1750866966.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 106,115

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan adopted August 30, 2024.

Read SEC document
June 23, 2025 Filed Jun 25, 2025 15:56 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 6,543 $5.26 $34,416.18
Disclosure

SEC source: 0001691421-25-000099 · wk-form4_1750866966.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 112,658

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.

Read SEC document
June 03, 2025 Filed Jun 6, 2025 00:04 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 1,494 $35.25 $52,663.50
Disclosure

SEC source: 0001691421-25-000075 · wk-form4_1749168210.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 106,115

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

Read SEC document
April 02, 2025 Filed Apr 4, 2025 21:05 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 20,000 $0.00 Strike: $2.65 $0.00
Disclosure

SEC source: 0001691421-25-000045 · wk-form4_1743800694.xml · derivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: COMMON STOCK · 20,000 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.

F1 · derivative.exercise_date: The stock option is fully vested.

Read SEC document
April 02, 2025 Filed Apr 4, 2025 21:05 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 20,000 $2.65 $53,000.00
Disclosure

SEC source: 0001691421-25-000045 · wk-form4_1743800694.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 107,609

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.

Read SEC document
March 04, 2025 Filed Mar 6, 2025 23:26 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 1,899 $33.79 $64,167.21
Disclosure

SEC source: 0001691421-25-000037 · wk-form4_1741303611.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 87,609

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

Read SEC document
January 02, 2025 Filed Jan 4, 2025 00:18 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 10,000 $2.65 Strike: $2.65 $26,500.00
Disclosure

SEC source: 0001691421-25-000003 · wk-form4_1735949902.xml · derivative · entry 8

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 20,000

Underlying: COMMON STOCK · 10,000 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.

Read SEC document
January 02, 2025 Filed Jan 4, 2025 00:18 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 10,000 $2.65 $26,500.00
Disclosure

SEC source: 0001691421-25-000003 · wk-form4_1735949902.xml · nonDerivative · entry 5

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 89,508

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.

Read SEC document
December 31, 2024 Filed Jan 4, 2025 00:18 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 10,000 $2.65 Strike: $2.65 $26,500.00
Disclosure

SEC source: 0001691421-25-000003 · wk-form4_1735949902.xml · derivative · entry 7

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 30,000

Underlying: COMMON STOCK · 10,000 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.

Read SEC document
December 31, 2024 Filed Jan 4, 2025 00:18 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 10,000 $2.65 $26,500.00
Disclosure

SEC source: 0001691421-25-000003 · wk-form4_1735949902.xml · nonDerivative · entry 4

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 79,508

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.

Read SEC document
December 30, 2024 Filed Jan 4, 2025 00:18 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 10,000 $5.26 Strike: $5.26 $52,600.00
Disclosure

SEC source: 0001691421-25-000003 · wk-form4_1735949902.xml · derivative · entry 6

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 35,000

Underlying: COMMON STOCK · 10,000 shares

Expires 2028-03-27

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.

Read SEC document
December 30, 2024 Filed Jan 4, 2025 00:18 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 18,985 $38.67 $734,149.95
Disclosure

SEC source: 0001691421-25-000003 · wk-form4_1735949902.xml · nonDerivative · entry 3

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 69,508

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

Read SEC document
December 30, 2024 Filed Jan 4, 2025 00:18 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 10,000 $38.67 $386,700.00
Disclosure

SEC source: 0001691421-25-000003 · wk-form4_1735949902.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 88,493

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

Read SEC document
December 30, 2024 Filed Jan 4, 2025 00:18 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 10,000 $5.26 $52,600.00
Disclosure

SEC source: 0001691421-25-000003 · wk-form4_1735949902.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 98,493

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.

Read SEC document
December 03, 2024 Filed Dec 23, 2024 18:53 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 1,790 $45.50 $81,445.00
Disclosure

SEC source: 0001691421-24-000154 · wk-form4_1734980008.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 88,493

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

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September 04, 2024 Filed Sep 6, 2024 19:18 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 1,547 $18.84 $29,145.48
Disclosure

SEC source: 0001691421-24-000116 · wk-form4_1725650278.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 90,283

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

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June 24, 2024 Filed Jun 26, 2024 22:55 UTC Lemonade, Inc. LMND · Entity 4057 GrantCOMMON STOCK 17,889 $0.00 $0.00
Disclosure

SEC source: 0001691421-24-000090 · wk-form4_1719442551.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 91,830

F1 · shares: Represents an award of restricted stock units, which will vest in 8 equal quarterly installments beginning on September 1, 2024, 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.

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June 04, 2024 Filed Jun 6, 2024 23:31 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 1,026 $16.03 $16,446.78
Disclosure

SEC source: 0001691421-24-000069 · wk-form4_1717716690.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 73,941

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

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March 05, 2024 Filed Mar 6, 2024 23:59 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 1,106 $16.52 $18,271.12
Disclosure

SEC source: 0001691421-24-000036 · wk-form4_1709769579.xml · nonDerivative · entry 3

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 74,967

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

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March 01, 2024 Filed Mar 6, 2024 01:54 UTC Lemonade, Inc. LMND · Entity 4057 GrantCOMMON STOCK 4,025 $0.00 $0.00
Disclosure

SEC source: 0001691421-24-000033 · wk-form4_1709690034.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 77,509

F1 · shares: Represents an award of restricted stock units, which will vest in 16 equal quarterly installments beginning on March 1, 2024, 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.

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January 25, 2024 Filed Jan 29, 2024 22:46 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 10,000 $0.00 Strike: $2.65 $0.00
Disclosure

SEC source: 0001691421-24-000008 · wk-form4_1706568352.xml · derivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,000

Underlying: COMMON STOCK · 10,000 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.

F1 · derivative.exercise_date: The stock option is fully vested.

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January 25, 2024 Filed Jan 29, 2024 22:46 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 10,000 $2.65 $26,500.00
Disclosure

SEC source: 0001691421-24-000008 · wk-form4_1706568352.xml · nonDerivative · entry 1

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 73,484

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.

Read SEC document
December 05, 2023 Filed Mar 6, 2024 23:59 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 869 $17.70 $15,381.30
Disclosure

SEC source: 0001691421-24-000036 · wk-form4_1709769579.xml · nonDerivative · entry 2

Peters John Sheldon · CIK 0001816299 · Chief Insurance Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 76,073

F1 · kind: The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.