Stock-based Compensation (Tables)

12 Months Ended

Dec. 31, 2023

Share-Based Payment Arrangement [Abstract]

Fair value assumptions

The fair value of each option granted during the year ended December 31, 2023 and 2022 is estimated on the date of grant using the Black-Scholes model with the following assumptions:

	December 31,
	2023	2022
Weighted average expected term (years)	6.00	6.10
Risk-free interest rate	4.2%	2.7%
Volatility	74%	47%
Expected dividend yield	0%	0%

Stock options activity

The following tables summarize activity of stock options and restricted stock units (“RSU’s”) ($ 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, 2022 (1)	9,760,657	$	39.43	8.17	$	8.05
Granted	1,056,332	15.77
Exercised	(103,350)	5.30
Canceled/forfeited	(1,118,382)	38.44
Outstanding as of December 31, 2023	9,595,257	$	37.26	7.21	$	10.30
Options exercisable as of December 31, 2023	4,686,527	$	30.07	6.12	$	9.41
Options unvested as of December 31, 2023	4,908,730	$	44.12	8.26	$	0.89

(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, 2022 (1)	1,651,243	$	27.92
Granted	3,396,302	16.24
Vested	(785,323)	24.40
Canceled/forfeited	(693,487)	21.73
Outstanding as of December 31, 2023	3,568,735	18.76

(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 are included and classified in the consolidated statements of operations and comprehensive loss, including assumed awards from the Metromile Acquisition is as follows ($ in millions):

	December 31,
	2023		2022		2021
Loss and loss adjustment expense, net	$	2.8	$	2.7	$	1.5
Other insurance expense	2.2		1.6		1.0
Sales and marketing (1)	6.4		6.6		5.1
Technology development	25.7		24.4		18.2
General and administrative	22.8		24.0		18.3
Total stock-based compensation expense	$	59.9	$	59.3	$	44.1

(1) Includes compensation expense related to warrant shares of $2.5 million for the year ended December 31, 2023.

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,
	2023		2022		2021
Stock options	$	37.6	$	47.8	$	40.1
RSUs	19.8		11.5		4.0
Warrant shares	2.5		—		—
Total stock-based compensation expense	$	59.9	$	59.3	$	44.1