Stock-based Compensation (Tables)

6 Months Ended

Jun. 30, 2020

Share-based Payment Arrangement [Abstract]

The fair value of each option granted during the six months ended June 30, 2020 and 2019 is estimated on the date of grant using the Black-Scholes model with the following assumptions:


	Six Months Ended June 30,
	2020	2019
Weighted average expected term (years)	6.1	6.1
Risk-free interest rate	1.0%	2.5%
Volatility	40%	50%
Expected dividend yield	0%	0%

Stock options activity

The following table summarizes activity of stock options ($ in millions, except for option and average amounts):


	Number of Options	Weighted- Average Exercise Price		Weighted-Average Remaining Contractual Term (Years)	Aggregate Intrinsic Value
Outstanding as of December 31, 2019	4,048,802	$	13.27	8.8	$	42.2
Granted	707,030	24.41
Exercised	(84,936)	2.08
Cancelled	(92,376)	20.28
Outstanding as of June 30, 2020	4,578,520	$	15.06	8.6	$	43.1

Options exercisable as of June 30, 2020	1,222,898	$	4.79	7.3	$	24.1
Options vested and expected to vest as of June 30, 2020	4,578,520	$	15.06	8.6	$	43.1

Stock-based compensation expense

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


	Three Months Ended June 30,						Six Months Ended June 30,
	2020		2019		2020		2019
Loss and loss adjustment expense, net	$	0.1	$	—	$	0.1	$	—
Other insurance expense	0.2		0.1		0.4		0.2
Sales and marketing	0.6		0.1		1.3		0.2
Technology development	0.7		0.1		1.3		0.1
General and administrative	0.8		0.1		1.5		0.3
Total stock-based compensation expense	$	2.4	$	0.4	$	4.6	$	0.8