Stock-based Compensation (Tables)

3 Months Ended

Mar. 31, 2021

Share-based Payment Arrangement [Abstract]

Fair value assumptions

The fair value of each option granted for the three months ended March 31, 2021 and 2020 is estimated on the date of grant using the Black-Scholes model based on the following assumptions:

	Three Months Ended March 31,
	2021	2020
Weighted average expected term (years)	6.1	6.1
Risk-free interest rate	0.7%	1.3%
Volatility	50%	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	627,550	132.01
Exercised	(577,162)	10.64
Cancelled	(153,483)	32.36
Outstanding as of March 31, 2021	4,841,616	$	35.29	8.32	$	303.92
Options exercisable as of March 31, 2021	1,557,787	$	11.29	7.34	$	127.49
Options unvested as of March 31, 2021	3,283,829	$	46.68	8.78	$	176.43

Restricted stock units activity

Restricted Stock Units

	Number of shares	Grant Date Fair Value
Outstanding as of December 31, 2020	—	—
Granted	50,250	$	159.02
Vested	—	—
Cancelled	—	—
Outstanding as of March 31, 2021	50,250	$	159.02

Stock-based compensation expense

Stock-based compensation expense was classified in the condensed consolidated statements of operations as follows ($ in millions):

	Three Months Ended March 31,
	2021		2020
Loss and loss adjustment expense, net	$	0.2	$	—
Other insurance expense	0.2		0.2
Sales and marketing	1.1		0.7
Technology development	0.7		0.6
General and administrative	3.9		0.7
Total stock-based compensation expense	$	6.1	$	2.2

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

	Three Months Ended March 31,
	2021		2020
Stock options	$	5.5	$	2.2
RSUs	0.6		—
Total stock-based compensation expense	$	6.1	$	2.2