Stock-based Compensation (Tables)

6 Months Ended

Jun. 30, 2021

Share-based Payment Arrangement [Abstract]

Fair value assumptions

The fair value of each option granted for the six months ended June 30, 2021 and 2020 is estimated on the date of grant using the Black-Scholes model based on the following assumptions:

	Six Months Ended June 30,
	2021	2020
Weighted average expected term (years)	6.3	6.1
Risk-free interest rate	1.3%	1.0%
Volatility	49%	40%
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, 2020	4,944,711	$	20.50	8.30	$	506.58
Granted	2,052,325	102.81
Exercised	(739,186)	10.56
Cancelled	(223,241)	39.21
Outstanding as of June 30, 2021	6,034,609	$	48.65	8.51	$	382.66
Options exercisable as of June 30, 2021	1,720,686	$	13.51	7.20	$	165.22
Options unvested as of June 30, 2021	4,313,923	$	62.65	9.03	$	217.44

Restricted stock units activity

Restricted Stock Units

	Number of shares	Grant Date Fair Value
Outstanding as of December 31, 2020	—	$	—
Granted	57,004	151.58
Vested	—	—
Cancelled	(1,875)	159.02
Outstanding as of June 30, 2021	55,129	$	151.33

Stock-based compensation expense

Stock-based compensation expense from stock options and RSUs granted included and classified in the condensed consolidated statements of operations for the six months ended June 30, 2021 and 2020 is as follows ($ in millions):

	Three Months Ended June 30,				Six Months Ended June 30,
	2021		2020		2021		2020
Loss and loss adjustment expense, net	$	0.5	$	0.1	$	0.7	$	0.1
Other insurance expense	0.2		0.2		0.4		0.4
Sales and marketing	1.3		0.6		2.4		1.3
Technology development	6.8		0.7		7.5		1.3
General and administrative	3.1		0.8		7.0		1.5
Total stock-based compensation expense	$	11.9	$	2.4	$	18.0	$	4.6

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,
	2021		2020		2021		2020
Stock options	$	10.5	$	2.4	$	16.0	$	4.6
RSUs	1.4		—		2.0		—
Total stock-based compensation expense	$	11.9	$	2.4	$	18.0	$	4.6

The total unrecognized expense granted to employees and non-employees outstanding at June 30, 2021 was $108.2 million for the stock options and $6.4 million for the RSUs, with a remaining weighted-average vesting period of 1.5 years for the stock options and 1.5 years for the RSUs.