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Stock-based Compensation (Tables)

9 Months Ended

Sep. 30, 2021

Share-based Payment Arrangement [Abstract]

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


	Nine Months Ended September 30,
	2021	2020
Weighted average expected term (years)	6.1	6.1
Risk-free interest rate	1.3%	0.8%
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	2,319,085	91.13
Exercised	(810,575)	10.68
Cancelled	(420,423)	49.50
Outstanding as of September 30, 2021	6,032,798	$	46.58	8.38	$	177.06
Options exercisable as of September 30, 2021	1,953,806	$	15.52	7.21	$	101.42
Options unvested as of September 30, 2021	4,078,992	$	61.45	8.94	$	75.64

Restricted stock units activity

Restricted Stock Units


	Number of shares	Grant Date Fair Value
Outstanding as of December 31, 2020	—	$	—
Granted	144,254	109.50
Vested	(12,108)	159.02
Cancelled	(1,905)	157.76
Outstanding as of September 30, 2021	130,241	$	104.19

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 nine months ended September 30, 2021 and 2020 is as follows ($ in millions):


	Three Months Ended September 30,				Nine Months Ended September 30,
	2021		2020		2021		2020
Loss and loss adjustment expense, net	$	0.3	$	0.1	$	1.0	$	0.2
Other insurance expense	0.4		0.1		0.8		0.5
Sales and marketing	1.4		0.8		3.8		2.1
Technology development	5.3		0.8		12.8		2.1
General and administrative	5.3		0.9		12.3		2.4
Total stock-based compensation expense	$	12.7	$	2.7	$	30.7	$	7.3

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 September 30,				Nine Months Ended September 30,
	2021		2020		2021		2020
Stock options	$	12.0	$	2.7	$	28.0	$	7.3
RSUs	0.7		—		2.7		—
Total stock-based compensation expense	$	12.7	$	2.7	$	30.7	$	7.3