LMND · Lemonade, Inc. · Insider Trading

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

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.

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.

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.

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

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.

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.

Represents sale pursuant to a Rule 10b5-1 trading plan, adopted on March 13, 2026.

The price reported in Column 4 is a weighted average price, these shares were sold in multiple transactions ranging from $76.03 to $81.13. 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.

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

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

Represents an award of restricted stock units, which will vest and become exercisable 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 3, 2027. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

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 3, 2027. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

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 3, 2027. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

Represents an award of restricted stock units, which will vest and become exercisable 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 3, 2027. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

Represents an award of restricted stock units, which will vest and become exercisable 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 3, 2027. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock.

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.

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.

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.

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

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

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

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

The original Form 4 listed a Transaction Code of "A", and should have had Transaction Code of "P", as these were purchases of common stock on the open market.

The Reporting Person is Co-Trustee of Smith Family Trust dated November 9, 2013 ("Trust") and has voting and dispositive control over the shares held by Trust.

The original Form 4 listed a Transaction Code of "A", and should have had Transaction Code of "P", as these were purchases of common stock on the open market.

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.

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 RSUs 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.

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.

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

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.

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.

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.

The option is fully vested and exercisable.

Represents sale pursuant to a Rule 10b5-1 trading plan, adopted on December 11, 2024.

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.

The Reporting Person is Chief Executive Officer of Dan and Dan Ltd. ("Dan") and has voting and dispositive control over the shares held by Dan.

Represents sale pursuant to a Rule 10b5-1 trading plan, adopted on December 11, 2024.

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.

The Reporting Person is Chief Executive Officer of Dan and Dan Ltd. ("Dan") and has voting and dispositive control over the shares held by Dan.

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

The option is fully vested and exercisable.

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

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

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.

The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions prices ranging from $83.56 to $83.76, 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 purchased at each separate price within the range set forth in this footnote.

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

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.

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

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

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

This stock option is fully vested.