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Stock-based Compensation (Tables)
 12 Months Ended
Dec. 31, 2025
Share-Based Payment Arrangement [Abstract]  
Schedule of Fair value assumptions
The fair value of each option granted during the years ended December 31, 2025 and 2024 is estimated on the date of grant using the Black-Scholes model with the following assumptions:
December 31,
20252024
Weighted average expected term (years)5.85.8
Risk-free interest rate4.0%4.1%
Volatility81%77%
Expected dividend yield0%0%
Schedule of Stock options activity
The following tables summarize activity of stock options and restricted stock units (“RSU’s”):
Stock options
Number of
Options		 Weighted-
Average
Exercise
Price		 Weighted-
Average
Remaining
Contractual
Term
(Years)		 Aggregate
Intrinsic
Value
($ in millions)
Outstanding as of December 31, 2024
9,376,193 $36.03 6.81$106.8 
Granted
608,928 $58.31 
Exercised(1,346,225)$23.73 
Canceled/forfeited
(1,385,045)$85.55 
Outstanding as of December 31, 20257,253,851 $30.76 6.39$302.9 
Options exercisable as of December 31, 20255,295,891 $30.71 5.74$224.0 
Options unvested as of December 31, 20251,957,960 $30.91 8.15$78.9 
Schedule of Restricted stock units
Restricted Stock Units
Number of sharesGrant Date Fair Value
Outstanding as of December 31, 2024
4,278,383 $20.00 
Granted
1,189,864 $49.90 
Vested(1,840,124)$21.62 
Canceled/forfeited
(432,051)$21.59 
Outstanding as of December 31, 2025
3,196,072 $29.98 
Schedule of Stock-based compensation expense
Stock-based compensation expense from stock options and RSUs, including equity awards from the Assumed Plans as discussed above and warrants (Note 15), were included and presented in the consolidated statements of operations and comprehensive income (loss) as follows ($ in millions):
December 31,
202520242023
Loss and loss adjustment expense, net$2.3 $2.1 $2.8 
Other insurance expense2.9 2.5 2.2 
Sales and marketing (1)
(1.5)10.6 6.4 
Technology development29.1 26.2 25.7 
General and administrative28.5 23.1 22.8 
Total stock-based compensation expense$61.3 $64.5 $59.9 
(1)    Includes the impact of the canceled unvested warrant shares for contract year 2 related to the termination of the Warrant Agreement with Chewy in the amount of $5.2 million for the year ended December 31, 2025, and compensation expense related to warrant shares of $6.5 million and $2.5 million for the years ended December 31, 2024 and 2023.
Stock-based compensation expense classified by award type as included in the consolidated statements of operations and comprehensive income (loss) is as follows ($ in millions):

December 31,
202520242023
Stock options$25.2 $29.8 $37.6 
RSUs41.3 28.2 19.8 
Warrant shares
(5.2)6.5 2.5 
Total stock-based compensation expense$61.3 $64.5 $59.9