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Eckstein Adina

Disclosed activity across 1 company

Tapewire entity
61771
SEC CIK
0001874702

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
Lemonade, Inc.LMND · Entity 4057Chief Operating OfficerMarch 08, 2026March 10, 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 March 08, 2026 · Filed March 10, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
COMMON STOCKSEC Table I · non-derivativeDirect333,503 Reported balance After 2026-03-08 transaction · row 1
1 source row

Row 1 · 2026-03-08 · Grant · Acquired 145,112 · Balance 333,503

F1: 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 begin 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.

STOCK OPTIONSEC Table II · derivative / convertible security · Conversion / exercise price $55.13 · Expires 2036-03-08Direct54,417 Reported balance After 2026-03-08 transaction · row 2 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 2 · 2026-03-08 · Grant · Acquired 54,417 · Balance 54,417

F2: Represents an option award, which will vest and become exercisable in quarterly installments over 8 years, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date. The awards begin vesting quarterly on June 8, 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 option represents a contingent right to receive one share of the Issuer's common stock.

Filing footnotes · ownership attribution and instrument terms

F1: 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 begin 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.

F2: Represents an option award, which will vest and become exercisable in quarterly installments over 8 years, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date. The awards begin vesting quarterly on June 8, 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 option represents a contingent right to receive one share of the Issuer's common stock.

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
March 08, 2026 Filed Mar 10, 2026 16:53 UTC Lemonade, Inc. LMND · Entity 4057 GrantSTOCK OPTION · Derivative 54,417 $0.00 Strike: $55.13 $0.00
Disclosure

SEC source: 0001874702-26-000002 · wk-form4_1773175979.xml · derivative · entry 2

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 54,417

Underlying: COMMON STOCK · 54,417 shares

Expires 2036-03-08

F2 · derivative.exercise_date: Represents an option award, which will vest and become exercisable in quarterly installments over 8 years, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date. The awards begin vesting quarterly on June 8, 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 option represents a contingent right to receive one share of the Issuer's common stock.

Read SEC document
March 08, 2026 Filed Mar 10, 2026 16:53 UTC Lemonade, Inc. LMND · Entity 4057 GrantCOMMON STOCK 145,112 $0.00 $0.00
Disclosure

SEC source: 0001874702-26-000002 · wk-form4_1773175979.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 333,503

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 begin 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.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 16:35 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 7,919 $84.15 $666,383.85
Disclosure

SEC source: 0001874702-25-000012 · wk-form4_1765834523.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 188,391

F1 · shares: Represents sale pursuant to a Rule 10b5-1 trading plan adopted on September 8, 2025.

F2 · 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.

Read SEC document
December 10, 2025 Filed Dec 11, 2025 17:14 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 7,919 $81.15 $642,626.85
Disclosure

SEC source: 0001874702-25-000010 · wk-form4_1765491244.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 196,310

F1 · shares: Represents sale pursuant to a Rule 10b5-1 trading plan adopted on September 8, 2025.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were purchased 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 purchased at each separate price.

Read SEC document
December 09, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 29,237 $44.57 Strike: $44.57 $1,303,093.09
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · derivative · entry 10

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 4,514

Underlying: COMMON STOCK · 29,237 shares

Expires 2031-12-06

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 option began vesting and became exercisable in 16 equal quarterly installments beginning on March 6, 2022.

Read SEC document
December 09, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 29,237 $77.17 $2,256,219.29
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · nonDerivative · entry 7

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 204,229

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan, adopted September 8, 2025.

Read SEC document
December 09, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 29,237 $44.57 $1,303,093.09
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · nonDerivative · entry 6

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 233,466

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 08, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 1,549 $44.57 Strike: $44.57 $69,038.93
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · derivative · entry 9

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 33,751

Underlying: COMMON STOCK · 1,549 shares

Expires 2031-12-06

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 option began vesting and became exercisable in 16 equal quarterly installments beginning on March 6, 2022.

Read SEC document
December 08, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 16,250 $24.47 Strike: $24.47 $397,637.50
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · derivative · entry 8

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 0

Underlying: COMMON STOCK · 16,250 shares

Expires 2030-06-06

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: This stock option is fully vested.

Read SEC document
December 08, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 7,919 $78.94 $625,125.86
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · nonDerivative · entry 5

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 204,229

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan, adopted September 8, 2025.

Read SEC document
December 08, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 15,839 $78.92 $1,250,013.88
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · nonDerivative · entry 4

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 212,148

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan, adopted September 8, 2025.

Read SEC document
December 08, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 17,799 $78.97 $1,405,587.03
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · nonDerivative · entry 3

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 227,987

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan, adopted September 8, 2025.

Read SEC document
December 08, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 1,549 $44.57 $69,038.93
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · nonDerivative · entry 2

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 245,786

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 08, 2025 Filed Dec 10, 2025 17:56 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 16,250 $24.47 $397,637.50
Disclosure

SEC source: 0001874702-25-000007 · wk-form4_1765407409.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 244,237

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
November 10, 2025 Filed Nov 12, 2025 16:58 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 5,988 $27.35 Strike: $27.35 $163,771.80
Disclosure

SEC source: 0001874702-25-000005 · wk-form4_1762984722.xml · derivative · entry 8

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,074

Underlying: COMMON STOCK · 5,988 shares

Expires 2032-04-05

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: This stock option is fully vested.

Read SEC document
November 10, 2025 Filed Nov 12, 2025 16:58 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 5,988 $78.00 $467,064.00
Disclosure

SEC source: 0001874702-25-000005 · wk-form4_1762984722.xml · nonDerivative · entry 6

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 227,987

Read SEC document
November 10, 2025 Filed Nov 12, 2025 16:58 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 5,988 $27.35 $163,771.80
Disclosure

SEC source: 0001874702-25-000005 · wk-form4_1762984722.xml · nonDerivative · entry 5

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 233,975

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
November 07, 2025 Filed Nov 12, 2025 16:58 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 40,000 $27.35 Strike: $27.35 $1,094,000.00
Disclosure

SEC source: 0001874702-25-000005 · wk-form4_1762984722.xml · derivative · entry 7

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 13,062

Underlying: COMMON STOCK · 40,000 shares

Expires 2032-04-05

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: This stock option is fully vested.

Read SEC document
November 07, 2025 Filed Nov 12, 2025 16:58 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 20,000 $74.00 $1,480,000.00
Disclosure

SEC source: 0001874702-25-000005 · wk-form4_1762984722.xml · nonDerivative · entry 4

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 227,987

Read SEC document
November 07, 2025 Filed Nov 12, 2025 16:58 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 20,000 $27.35 $547,000.00
Disclosure

SEC source: 0001874702-25-000005 · wk-form4_1762984722.xml · nonDerivative · entry 3

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 247,987

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
November 07, 2025 Filed Nov 12, 2025 16:58 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 20,000 $72.04 $1,440,800.00
Disclosure

SEC source: 0001874702-25-000005 · wk-form4_1762984722.xml · nonDerivative · entry 2

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 227,987

Read SEC document
November 07, 2025 Filed Nov 12, 2025 16:58 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 20,000 $27.35 $547,000.00
Disclosure

SEC source: 0001874702-25-000005 · wk-form4_1762984722.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 247,987

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 21, 2025 Filed Aug 25, 2025 18:30 UTC Lemonade, Inc. LMND · Entity 4057 GrantCOMMON STOCK 38,334 $0.00 $0.00
Disclosure

SEC source: 0001874702-25-000003 · wk-form4_1756161013.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 227,987

F1 · shares: Represents an award of restricted stock units, which will vest in 12 equal quarterly installments beginning on August 1, 2025, 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
August 13, 2025 Filed Aug 15, 2025 16:11 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 5,000 $24.47 Strike: $24.47 $122,350.00
Disclosure

SEC source: 0001691421-25-000131 · wk-form4_1755288696.xml · derivative · entry 3

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,250

Underlying: COMMON STOCK · 5,000 shares

Expires 2030-06-06

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
August 13, 2025 Filed Aug 15, 2025 16:11 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 5,000 $58.00 $290,000.00
Disclosure

SEC source: 0001691421-25-000131 · wk-form4_1755288696.xml · nonDerivative · entry 2

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 189,653

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024.

Read SEC document
August 13, 2025 Filed Aug 15, 2025 16:11 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 5,000 $24.47 $122,350.00
Disclosure

SEC source: 0001691421-25-000131 · wk-form4_1755288696.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 189,653

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 11, 2025 Filed Aug 13, 2025 18:02 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 5,000 $24.47 Strike: $24.47 $122,350.00
Disclosure

SEC source: 0001691421-25-000128 · wk-form4_1755122554.xml · derivative · entry 3

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 21,250

Underlying: COMMON STOCK · 5,000 shares

Expires 2030-06-06

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
August 11, 2025 Filed Aug 13, 2025 18:02 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 0 $53.00 $0.00
Disclosure

SEC source: 0001691421-25-000128 · wk-form4_1755122554.xml · nonDerivative · entry 2

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 189,653

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024.

Read SEC document
August 11, 2025 Filed Aug 13, 2025 18:02 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 0 $24.47 $0.00
Disclosure

SEC source: 0001691421-25-000128 · wk-form4_1755122554.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 189,653

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 05, 2025 Filed Aug 7, 2025 17:33 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 3,750 $24.47 Strike: $24.47 $91,762.50
Disclosure

SEC source: 0001691421-25-000126 · wk-form4_1754602399.xml · derivative · entry 5

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 26,250

Underlying: COMMON STOCK · 3,750 shares

Expires 2030-06-06

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
August 05, 2025 Filed Aug 7, 2025 17:33 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 1,250 $23.69 Strike: $23.69 $29,612.50
Disclosure

SEC source: 0001691421-25-000126 · wk-form4_1754602399.xml · derivative · entry 4

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 0

Underlying: COMMON STOCK · 1,250 shares

Expires 2029-09-25

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
August 05, 2025 Filed Aug 7, 2025 17:33 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 5,000 $49.00 $245,000.00
Disclosure

SEC source: 0001691421-25-000126 · wk-form4_1754602399.xml · nonDerivative · entry 3

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 189,653

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024.

Read SEC document
August 05, 2025 Filed Aug 7, 2025 17:33 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 3,750 $23.69 $88,837.50
Disclosure

SEC source: 0001691421-25-000126 · wk-form4_1754602399.xml · nonDerivative · entry 2

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 194,653

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 05, 2025 Filed Aug 7, 2025 17:33 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 1,250 $23.69 $29,612.50
Disclosure

SEC source: 0001691421-25-000126 · wk-form4_1754602399.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 190,903

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 23, 2025 Filed Jun 25, 2025 12:11 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 5,000 $23.69 Strike: $23.69 $118,450.00
Disclosure

SEC source: 0001691421-25-000103 · wk-form4_1750867857.xml · derivative · entry 3

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 1,250

Underlying: COMMON STOCK · 5,000 shares

Expires 2029-09-25

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 12:11 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 5,000 $45.00 $225,000.00
Disclosure

SEC source: 0001691421-25-000103 · wk-form4_1750867857.xml · nonDerivative · entry 2

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 189,653

F1 · kind: Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024.

Read SEC document
June 23, 2025 Filed Jun 25, 2025 12:11 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 5,000 $23.69 $118,450.00
Disclosure

SEC source: 0001691421-25-000103 · wk-form4_1750867857.xml · nonDerivative · entry 1

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 194,653

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
November 21, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 6,875 $23.69 Strike: $23.69 $162,868.75
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · derivative · entry 18

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 6,250

Underlying: COMMON STOCK · 6,875 shares

Expires 2029-09-25

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.

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November 21, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 1,769 $27.35 Strike: $27.35 $48,382.15
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · derivative · entry 17

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 53,062

Underlying: COMMON STOCK · 1,769 shares

Expires 2032-04-05

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: Represents an award of stock options, which vest in 16 equal quarterly installments which began on July 5, 2022, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date.

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November 21, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 15,000 $24.47 Strike: $24.47 $367,050.00
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · derivative · entry 16

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 30,000

Underlying: COMMON STOCK · 15,000 shares

Expires 2030-06-06

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
November 21, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 6,875 $50.00 $343,750.00
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · nonDerivative · entry 12

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 189,653

F1 · kind: The reported transaction occurred pursuant to a trading plan intended to comply with Rule 10b5-1(c) and adopted on June 14, 2024.

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November 21, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 1,769 $50.00 $88,450.00
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · nonDerivative · entry 11

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 196,528

F1 · kind: The reported transaction occurred pursuant to a trading plan intended to comply with Rule 10b5-1(c) and adopted on June 14, 2024.

Read SEC document
November 21, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 15,000 $50.00 $750,000.00
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · nonDerivative · entry 10

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 198,297

F1 · kind: The reported transaction occurred pursuant to a trading plan intended to comply with Rule 10b5-1(c) and adopted on June 14, 2024.

Read SEC document
November 21, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 6,875 $23.69 $162,868.75
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · nonDerivative · entry 9

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 213,297

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
November 21, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 1,769 $27.35 $48,382.15
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · nonDerivative · entry 8

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 206,422

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
November 21, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionCOMMON STOCK 15,000 $24.47 $367,050.00
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · nonDerivative · entry 7

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 204,653

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
November 19, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 6,875 $23.69 Strike: $23.69 $162,868.75
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · derivative · entry 15

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 13,125

Underlying: COMMON STOCK · 6,875 shares

Expires 2029-09-25

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
November 19, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 1,769 $27.35 Strike: $27.35 $48,382.15
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · derivative · entry 14

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 54,831

Underlying: COMMON STOCK · 1,769 shares

Expires 2032-04-05

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: Represents an award of stock options, which vest in 16 equal quarterly installments which began on July 5, 2022, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date.

Read SEC document
November 19, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 Exercise / conversionSTOCK OPTION · Derivative 15,000 $24.47 Strike: $24.47 $367,050.00
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · derivative · entry 13

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 45,000

Underlying: COMMON STOCK · 15,000 shares

Expires 2030-06-06

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
November 19, 2024 Filed Nov 21, 2024 21:42 UTC Lemonade, Inc. LMND · Entity 4057 SaleCOMMON STOCK 6,875 $40.00 $275,000.00
Disclosure

SEC source: 0001691421-24-000148 · wk-form4_1732243329.xml · nonDerivative · entry 6

Eckstein Adina · CIK 0001874702 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 189,653

F1 · kind: The reported transaction occurred pursuant to a trading plan intended to comply with Rule 10b5-1(c) and adopted on June 14, 2024.

Read SEC document

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