Stock-based Compensation (Tables)

12 Months Ended

Dec. 31, 2020

Share-based Payment Arrangement [Abstract]

The fair value of each option granted during the year ended December 31, 2020 and 2019 is estimated on the date of grant using the Black-Scholes model with the following assumptions (annualized percentage):


	December 31,
	2020	2019
Weighted average expected term (years)	6.09	6.06
Risk-free interest rate	0.7%	1.7%
Volatility	40%	45%
Expected dividend yield	0%	0%

Stock options activity

The following table summarizes activity ($ 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	8.83	$	42.20
Granted	1,325,030	38.32
Exercised	(282,422)	6.86
Cancelled	(146,699)	23.68
Outstanding as of December 31, 2020	4,944,711	$	20.50	8.30	$	506.58
Options exercisable as of December 31, 2020	1,766,466	$	9.64	7.35	$	199.37
Options unvested as of December 31, 2020	3,178,245	$	25.84	8.82	$	307.22

Stock-based compensation expense

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


	Years Ended December 31
	2020		2019		2018
Loss and loss adjustment expense, net	$	0.4	$	—	$	—
Other insurance expense	0.7		0.6		0.2
Sales and marketing	2.7		1.1		$	0.3
Technology development	3.1		1.4		$	0.1
General and administrative	3.7		1.2		$	1.5
Total stock-based compensation expense	$	10.6	$	4.3	$	2.1