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Stock-based Compensation (Tables)
 12 Months Ended
Dec. 31, 2021
Share-based Payment Arrangement [Abstract]  
Fair value assumptions
The fair value of each option granted during the year ended December 31, 2021 and 2020 is estimated on the date of grant using the Black-Scholes model with the following assumptions (annualized percentage):
December 31,
20212020
Weighted average expected term (years)6.136.09
Risk-free interest rate1.3%0.7%
Volatility48%40%
Expected dividend yield0%0%
Stock options activity
The following table summarizes activity ($ in millions, except for option and average amounts):
Stock options
Number of
Options		 Weighted-
Average
Exercise
Price		 Weighted-
Average
Remaining
Contractual
Term
(Years)		 Aggregate
Intrinsic
Value
Outstanding as of December 31, 20204,944,711 $20.50 8.30$506.58 
Granted3,054,135 79.97 
Exercised(848,992)10.87 
Cancelled(576,110)54.78 
Outstanding as of December 31, 20216,573,744 $46.03 8.29$85.86 
Options exercisable as of December 31, 20212,269,352 $19.31 7.09$58.35 
Options unvested as of December 31, 20214,304,392 $60.12 8.93$27.51 
Restricted stock units
Restricted Stock Units
Number of sharesGrant Date Fair Value
Outstanding as of December 31, 2020— $— 
Granted362,624 71.41 
Vested(19,063)143.49 
Cancelled(7,747)87.54 
Outstanding as of December 31, 2021335,814 66.94 
Stock-based compensation expense
Stock-based compensation expense from stock options and RSUs granted included and classified in the consolidated statements of operations and comprehensive loss is as follows ($ in millions):
December 31,
202120202019
Loss and loss adjustment expense, net$1.5 $0.4 $— 
Other insurance expense1.0 0.7 0.6 
Sales and marketing5.1 2.7 1.1 
Technology development18.2 3.1 1.4 
General and administrative18.3 3.7 1.2 
Total stock-based compensation expense$44.1 $10.6 $4.3 
Stock-based compensation expense classified by award type as included in the consolidated statements of operations and comprehensive loss is as follows ($ in millions):

December 31,
202120202019
Stock options$40.1 $10.6 $4.3 
RSUs4.0 — — 
Total stock-based compensation expense$44.1 $10.6 $4.3