Stock-based Compensation (Tables)

12 Months Ended

Dec. 31, 2022

Share-Based Payment Arrangement [Abstract]

Fair value assumptions

The fair value of each option granted during the year ended December 31, 2022 and 2021 is estimated on the date of grant using the Black-Scholes model with the following assumptions:

	December 31,
	2022	2021
Weighted average expected term (years)	6.10	6.13
Risk-free interest rate	2.7%	1.3%
Volatility	47%	48%
Expected dividend yield	0%	0%

Stock options activity

The following table summarizes activity ($ in millions, except for option and weighted-average amounts):

Stock options

	Number of Options	Weighted- Average Exercise Price		Weighted- Average Remaining Contractual Term (Years)	Aggregate Intrinsic Value
Outstanding as of December 31, 2021	6,573,744	$	46.03	8.29	$	85.86
Granted (1)	4,351,371	27.47
Exercised	(448,368)	7.97
Canceled	(716,090)	50.11
Outstanding as of December 31, 2022	9,760,657	$	39.43	8.17	$	8.05
Options exercisable as of December 31, 2022	3,420,165	$	28.38	6.87	$	7.93
Options unvested as of December 31, 2022	6,340,492	$	45.37	8.89	$	0.11

(1) includes assumed options of 72,410 from Metromile Acquisition (See Note 5)

Restricted stock units

Restricted Stock Units

	Number of shares	Grant Date Fair Value
Outstanding as of December 31, 2021	335,814	$	66.94
Granted (1)	1,821,066	22.50
Vested	(263,732)	37.26
Canceled	(241,905)	27.42
Outstanding as of December 31, 2022	1,651,243	27.92

(1) includes assumed restricted stock units of 331,797 from the Metromile Acquisition (See Note 5)

Stock-based compensation expense

Stock-based compensation expense from stock options and RSUs granted included and classified in the consolidated statements of operations and comprehensive loss, including assumed awards from the Metromile Acquisition for the year ended December 31, 2022, as follows ($ in millions):

	December 31,
	2022		2021		2020
Loss and loss adjustment expense, net	$	2.7	$	1.5	$	0.4
Other insurance expense	1.6		1.0		0.7
Sales and marketing	6.6		5.1		2.7
Technology development	24.4		18.2		3.1
General and administrative	24.0		18.3		3.7
Total stock-based compensation expense	$	59.3	$	44.1	$	10.6

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

	December 31,
	2022		2021		2020
Stock options	$	47.8	$	40.1	$	10.6
RSUs	11.5		4.0		—
Total stock-based compensation expense	$	59.3	$	44.1	$	10.6