Lemonade, INC Form 4 insider transactions

Lemonade's Chief Business Officer, Maya Prosor, sold 198 shares of common stock at $72.74 per share to cover tax withholding obligations related to vested Restricted Stock Units.

Lemonade's Chief Insurance Officer, John Sheldon Peters, sold a total of 5,344 shares of common stock in early December 2025, partly for tax obligations and partly under a 10b5-1 plan.

Lemonade's Chief Insurance Officer, John Sheldon Peters, sold a total of 22,728 shares of common stock in two transactions in November 2025.

Lemonade's Chief Financial Officer, Timothy E. Bixby, reported a charitable donation of 6,000 shares and the sale of 30,000 shares from a family trust.

Lemonade Inc.'s Chief Operating Officer, Adina Eckstein, exercised stock options and subsequently sold the acquired common stock in pre-planned transactions.

Lemonade Inc. CEO Daniel Schreiber reported gifting 35,000 shares of common stock to a third party on November 11, 2025.

Lemonade, Inc. Director Geoff Seeley received an award of 3,119 restricted stock units, aligning his interests with shareholders.

Lemonade, Inc. Director Prashant Ratanchandani received an award of 3,337 restricted stock units, which will vest in three equal annual installments.

Lemonade Director Michael A. Eisenberg reported a charitable donation of 4,000 shares of common stock.

Lemonade's Chief Business Officer, Maya Prosor, sold 282 shares of common stock to cover tax withholding obligations related to RSU vesting.

Lemonade's Chief Insurance Officer, John Sheldon Peters, plans to sell 2,718 shares of common stock on September 3, 2025, for $50.34 per share to cover tax withholding obligations related to RSU vesting.

Lemonade's Chief Financial Officer, Timothy E. Bixby, sold 2,906 shares of common stock at $50.34 per share to cover tax withholding obligations related to Restricted Stock Unit vesting.

Lemonade, Inc. President and Director Shai Wininger was granted 127,780 stock options with an exercise price of $59.74, vesting quarterly over three years.

Lemonade's Chief Operating Officer, Adina Eckstein, was granted 38,334 restricted stock units, vesting quarterly starting August 1, 2025.

Lemonade, Inc. CEO Daniel Schreiber was granted 127,780 stock options with an exercise price of $59.74, vesting quarterly over ten years.

Lemonade's Chief Insurance Officer, John Sheldon Peters, was granted 25,556 stock options with an exercise price of $59.74, vesting quarterly starting August 18, 2025.

Lemonade's Chief Business Officer, Maya Prosor, was granted 76,668 stock options with an exercise price of $59.74, vesting quarterly over three years.

Lemonade, Inc. Chief Financial Officer Timothy Bixby was granted 127,780 stock options with an exercise price of $59.74, vesting quarterly over three years.

Lemonade's Chief Insurance Officer, John Peters, sold 38,155 shares for $60 each after exercising stock options, alongside a charitable donation.

Lemonade's Chief Operating Officer, Adina Eckstein, sold 5,000 shares of common stock for $58 per share after exercising options at $24.47 per share, as part of a pre-arranged trading plan.

Adina Eckstein, COO of Lemonade, Inc., sold shares of common stock on August 11, 2025, under a pre-arranged Rule 10b5-1 trading plan.

Lemonade Inc.'s Chief Operating Officer, Adina Eckstein, sold 5,000 shares of common stock for $49.00 per share after exercising stock options.

Lemonade Inc.'s Chief Financial Officer, Timothy E. Bixby, executed pre-planned transactions, exercising stock options and subsequently selling an equivalent number of shares under a Rule 10b5-1 trading plan.

Lemonade Inc.'s Chief Financial Officer, Timothy E. Bixby, exercised stock options and subsequently sold 5,000 shares of common stock for a gain, as part of a pre-arranged Rule 10b5-1 trading plan.

Lemonade Inc.'s Chief Financial Officer, Timothy Bixby, executed a pre-arranged trading plan on July 7, 2025, involving the exercise of stock options and subsequent sale of common stock.

Lemonade, Inc.'s Chief Financial Officer, Timothy E. Bixby, completed a pre-arranged transaction on June 30, 2025, involving the exercise of stock options and the subsequent sale of an equivalent number of common shares.

Lemonade, Inc.'s Chief Operating Officer, Adina Eckstein, reported the exercise of stock options and the subsequent sale of an equal number of common shares, executed under a pre-arranged 10b5-1 trading plan.

Lemonade, Inc.'s Chief Financial Officer, Timothy E. Bixby, exercised stock options and subsequently sold an equivalent number of common shares on June 23, 2025, as part of a pre-arranged 10b5-1 trading plan.

Lemonade, Inc.'s Chief Insurance Officer, John Sheldon Peters, exercised stock options and subsequently sold an equivalent number of common shares on June 23, 2025, as part of a pre-arranged trading plan.

Lemonade, Inc.'s Chief Financial Officer, Timothy E. Bixby, exercised stock options for 11,000 shares and simultaneously sold an equivalent number of shares on June 16, 2025, as part of a pre-arranged Rule 10b5-1 trading plan.