Stock-based Compensation (Tables)

3 Months Ended

Mar. 31, 2022

Share-based Payment Arrangement [Abstract]

Fair value assumptions

The fair value of each option granted for the three months ended March 31, 2022 and 2021 is estimated on the date of grant using the Black-Scholes model based on the following assumptions:

	Three Months Ended March 31,
	2022	2021
Weighted average expected term (years)	6.1	6.1
Risk-free interest rate	1.7%	0.7%
Volatility	48%	50%
Expected dividend yield	0%	0%

Stock options activity

Stock options

	Number of Options	Weighted- Average Exercise Price		Weighted-Average Remaining Contractual Term (Years)	Aggregate Intrinsic Value
Outstanding as of December 31, 2021	6,573,744	$	46.03	8.29	$	85.86
Granted	59,500	19.62
Exercised	(81,776)	7.86
Cancelled	(196,194)	60.91
Outstanding as of March 31, 2022	6,355,274	$	45.82	8.00	$	32.88
Options exercisable as of March 31, 2022	2,545,655	$	22.32	6.87	$	26.70
Options unvested as of March 31, 2022	3,809,619	$	61.52	8.76	$	6.18

Restricted stock units activity

Restricted Stock Units

	Number of shares	Grant Date Fair Value
Outstanding as of December 31, 2021	335,814	$	66.94
Granted	175,233	22.18
Vested	(15,967)	82.94
Cancelled	(19,331)	47.72
Outstanding as of March 31, 2022	475,749	$	50.69

Stock-based compensation expense

Stock-based compensation expense from stock options and RSUs granted as included and classified in the condensed consolidated statements of operations for the three months ended March 31, 2022 and 2021 is as follows ($ in millions):

	Three Months Ended March 31,
	2022		2021
Loss and loss adjustment expense, net	$	0.6	$	0.2
Other insurance expense	0.3		0.2
Sales and marketing	1.5		1.1
Technology development	5.4		0.7
General and administrative	6.3		3.9
Total stock-based compensation expense	$	14.1	$	6.1

Stock-based compensation expense classified by award type as included in the condensed consolidated statements of operations is as follows ($ in millions):

	Three Months Ended March 31,
	2022		2021
Stock options	$	12.1	$	5.5
RSUs	2.0		0.6
Total stock-based compensation expense	$	14.1	$	6.1