Stockholders’ Deficit (Tables)

6 Months Ended

Jun. 30, 2022

Equity [Abstract]

Share-based Payment Arrangement, Option, Activity

The following table summarizes option activity under the plans:

	Options Outstanding			Weighted-Average Remaining	Aggregate Intrinsic Value (In Millions)
	Number of Shares	Weighted Average Exercise Price		Contract Term (In Years)
Outstanding as of December 31, 2021	47,538,926	$	1.39	8.30	$	84.8
Granted	15,639,811	1.80
Exercised	(2,754,832)	0.62
Cancelled/Expired	(2,580,600)	1.56
Outstanding as of June 30, 2022	57,843,305	$	1.47	8.36	$	4.9
Vested and exercisable as of June 30, 2022	20,815,734	$	1.04	7.62	$	3.3

Schedule of Share-based Payment Award, Stock Options, Valuation Assumptions

The fair value of granted stock options was estimated as of the date of grant using the Black-Scholes-Merton option-pricing model, based on the following inputs:

	June 30,
	2022		2021
Expected term (in years)	5.0 - 6.7		5.8 - 6.1
Expected volatility	29.6% - 30.9%		29.7% - 30.1%
Risk-free interest rate	2.6% - 3.0%		0.6% - 1.0%
Expected dividend yield	—	%	—	%

Schedule of Share-based Payment Award, Performance Restricted Stock Units, Valuation Assumptions

The following table presents the assumptions utilized in the Monte Carlo valuation model for market-based awards for the period indicated:

	June 30,
	2022
Expected term (in years)	4.1
Expected volatility	95.0	%
Risk-free interest rate	2.9	%
Expected dividend yield	—	%

Schedule of Unvested Restricted Stock Units Roll Forward

The following table summarizes the RSU and PRSU activity for the six months ended June 30, 2022:

	Number of Shares	Weighted Average Grant-Date Fair Value per Share
Unvested and outstanding as of December 31, 2021	28,939,349	$	3.99
Granted	56,545,065	1.40
Released	(4,777,767)	3.67
Canceled and forfeited	(3,340,510)	3.51
Unvested and outstanding as of June 30, 2022	77,366,137	$	2.14

Share-based Payment Arrangement, Expensed and Capitalized, Amount

Total stock-based compensation expense, classified in the accompanying consolidated statements of operations and comprehensive loss was as follows (in millions):

	Three Months Ended				Six Months Ended
	June 30,				June 30,
	2022		2021		2022		2021
Losses and loss adjustment expenses	$	1.0	$	0.1	$	1.6	$	0.1
Insurance related expenses	1.2		—		2.5		0.1
Technology and development	5.8		0.5		11.1		1.0
Sales and marketing	3.1		1.2		5.4		2.1
General and administrative	4.8		1.0		8.7		2.0
Total stock-based compensation expense	$	15.9	$	2.8	$	29.3	$	5.3