Stock-based Compensation (Tables)

6 Months Ended

Jun. 30, 2022

Share-Based Payment Arrangement [Abstract]

Fair value assumptions

The fair value of each option granted for the six months ended June 30, 2022 and 2021 is estimated on the date of grant using the Black-Scholes model based on the following assumptions:

	Six Months Ended June 30,
	2022	2021
Weighted average expected term (years)	6.1	6.3
Risk-free interest rate	2.6%	1.3%
Volatility	47%	49%
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	2,906,961	27.20
Exercised	(170,362)	6.23
Cancelled	(405,797)	54.38
Outstanding as of June 30, 2022	8,904,546	$	40.26	8.38	$	15.73
Options exercisable as of June 30, 2022	2,725,019	$	24.36	6.72	$	14.32
Options unvested as of June 30, 2022	6,179,527	$	47.28	9.11	$	1.41

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	577,360	21.60
Vested	(36,219)	70.76
Cancelled	(39,666)	46.75
Outstanding as of June 30, 2022	837,289	$	36.47

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 and six months ended June 30, 2022 and 2021 is as follows ($ in millions):

	Three Months Ended June 30,				Six Months Ended June 30,
	2022		2021		2022		2021
Loss and loss adjustment expense, net	$	0.6	$	0.5	$	1.2	$	0.7
Other insurance expense	0.5		0.2		0.8		0.4
Sales and marketing	1.7		1.3		3.2		2.4
Technology development	5.8		6.8		11.2		7.5
General and administrative	5.3		3.1		11.6		7.0
Total stock-based compensation expense	$	13.9	$	11.9	$	28.0	$	18.0

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 June 30,				Six Months Ended June 30,
	2022		2021		2022		2021
Stock options	$	11.9	$	10.5	$	24.0	$	16.0
RSUs	2.0		1.4		4.0		2.0
Total stock-based compensation expense	$	13.9	$	11.9	$	28.0	$	18.0