Lemonade Inc SEC Filings

Lemonade, Inc. (LMND) – Form 4 filed 02-Jul-2025

Chief Financial Officer Timothy E. Bixby reported two same-day transactions dated 30-Jun-2025:

• Option exercise (Code “M”): 11,000 stock options exercised at an exercise price of $23.69.
• Open-market sale (Code “S”): the 11,000 resulting shares were sold at an average price of $42.69 under a Rule 10b5-1 plan adopted 12-Dec-2024.

After the transactions, Bixby’s direct ownership declined from 274,393 to 263,393 shares. He also holds 30,000 shares indirectly through the Timothy E. Bixby Family Trust, over which he has full voting and dispositive control. In addition, he retains 300,300 stock options outstanding after the exercise.

The option exercised was already fully vested and carries a 09-25-2029 expiration date. No other executives were included in this filing, and no operational or financial performance metrics were disclosed.

While insider sales can signal several motives (liquidity, diversification, tax), the modest size relative to Bixby’s remaining stake and the pre-arranged 10b5-1 plan suggest limited informational value for long-term shareholders.

Form 144 filing for Lemonade, Inc. (LMND) discloses a proposed sale of 11,000 common shares through Fidelity Brokerage Services on 06/30/2025. The shares carry an aggregate market value of $469,590, implying an indicative price of roughly $42.69 per share. Outstanding shares reported in the filing total 73,266,170, so the planned sale represents about 0.015 % of shares outstanding, a de-minimis ownership impact.

The form also summarizes insider activity over the preceding three months. Six transactions executed by Timothy E. Bixby between 06/03/2025 and 06/23/2025 amounted to 33,916 shares sold, yielding gross proceeds of ≈$1.394 million. Combining those sales with the new notice brings total disclosed dispositions to 44,916 shares since early June 2025.

While the filing does not list the seller’s formal relationship to the company, the repeated sales could signal ongoing personal liquidity moves or portfolio rebalancing. From a capital-structure perspective, the quantities are immaterial; however, continuing insider divestitures may weigh modestly on near-term investor sentiment.

Lemonade Chief Operating Officer Adina Eckstein executed a significant insider transaction on June 23, 2025, involving both the exercise of stock options and subsequent sale of shares:

• Exercised 5,000 stock options at $23.69 per share
• Immediately sold 5,000 shares at $45.00 per share
• The sale was conducted under a pre-established Rule 10b5-1 trading plan from December 5, 2024
• After the transactions, Eckstein holds 189,653 shares directly and 1,250 stock options

The transaction resulted in a gross profit of approximately $106,550 (($45.00 - $23.69) × 5,000 shares). The options were fully vested at the time of exercise, with an original expiration date of September 25, 2029.

Lemonade CFO Timothy E. Bixby reported significant insider trading activity on June 23, 2025. The transaction involved two key parts:

• Exercised 11,000 stock options at $23.69 per share through conversion (Transaction Code: M)
• Subsequently sold 11,000 shares at $43.36 per share under a pre-established Rule 10b5-1 trading plan from December 2024

Following these transactions, Bixby's holdings include:

• Direct ownership: 263,393 common shares and 311,300 stock options
• Indirect ownership: 30,000 shares held in the Timothy E. Bixby Family Trust

The exercised options were fully vested with an expiration date of September 25, 2029. This transaction resulted in a gross profit of approximately $216,370 (difference between sale price and option exercise price).

Lemonade Chief Insurance Officer John Peters executed significant stock transactions on June 23, 2025, as reported in this Form 4 filing. The transactions involved:

• Exercise of stock options for 6,543 shares at $5.26 per share
• Immediate sale of all 6,543 shares at $45.00 per share under a pre-established Rule 10b5-1 trading plan from August 30, 2024

Following these transactions, Peters retains 106,115 shares of common stock held directly, plus 28,457 vested stock options. The options have an exercise price of $5.26 and expire on March 27, 2028. This transaction pattern of exercising options and selling shares was executed according to a predetermined trading plan, suggesting planned portfolio management rather than a reactive market decision.

A Form 144 has been filed for Lemonade indicating a proposed sale of 5,000 shares of common stock with an aggregate market value of $221,550. The securities are to be sold through Oppenheimer & Co. Inc. on the NYSE, with an approximate sale date of June 23, 2025.

The shares were originally acquired through an Employee Stock Option Plan on December 24, 2019, with the filer receiving 20,000 shares from the issuer. Payment is to be made in cash upon execution of the sale.

Key details:

• Current shares outstanding: 73,266,170
• Sale price per share: approximately $44.31
• No other securities were sold by the filer during the past 3 months
• Transaction to be executed on the NYSE