Stock-based Compensation (Tables)

9 Months Ended

Sep. 30, 2024

Share-Based Payment Arrangement [Abstract]

Fair value assumptions

The fair value of each option granted for the nine months ended September 30, 2024 and 2023 is estimated on the date of grant using the Black-Scholes model based on the following assumptions:

	Nine Months Ended September 30,
	2024	2023
Weighted average expected term (years)	5.8	6.0
Risk-free interest rate	4.1%	4.2%
Volatility	77%	74%
Expected dividend yield	0%	0%

Stock options activity

The following tables summarize activity of stock options and restricted stock units ("RSUs"):

Stock options

	Number of Options	Weighted- Average Exercise Price		Weighted-Average Remaining Contractual Term (Years)	Aggregate Intrinsic Value
					($ in millions)
Outstanding as of December 31, 2023	9,595,257	$	37.26	7.21	$	10.30
Granted	1,206,367	$	15.94
Exercised	(33,361)	$	5.58
Canceled/Forfeited	(420,702)	$	40.48
Outstanding as of September 30, 2024	10,347,561	$	34.74	6.90	$	11.44
Options exercisable as of September 30, 2024	5,555,349	$	29.99	5.93	$	9.69
Options unvested as of September 30, 2024	4,792,212	$	40.26	8.02	$	1.75

Restricted stock units activity

Restricted Stock Units

	Number of Shares	Weighted Average Grant Date Fair Value
Outstanding as of December 31, 2023	3,568,735	$	18.76
Granted	2,107,790	$	16.66
Vested	(1,000,533)	$	19.64
Canceled/Forfeited	(353,080)	$	17.15
Outstanding as of September 30, 2024	4,322,912	$	17.63

Stock-based compensation expense

Stock-based compensation expense from stock options and RSUs, including equity awards from the Assumed Plans as discussed above and warrants (Note 10), are included and classified in the condensed consolidated statements of operations and comprehensive income as follows ($ in millions):

	Three Months Ended September 30,				Nine Months Ended September 30,
	2024		2023		2024		2023
Loss and loss adjustment expense, net	$	0.5	$	0.8	$	1.5	$	2.2
Other insurance expense	0.7		0.6		1.9		1.6
Sales and marketing (1)	3.0		1.9		7.6		4.6
Technology development	6.6		6.4		19.4		19.4
General and administrative	6.1		5.7		16.8		17.8
Total stock-based compensation expense	$	16.9	$	15.4	$	47.2	$	45.6

(1) Includes compensation expense related to warrant shares of $2.0 million and $4.5 million for the three and nine months ended September 30, 2024, respectively and $0.9 million and $1.5 million for the three and nine months ended September 30, 2023.

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

	Three Months Ended September 30,				Nine Months Ended September 30,
	2024		2023		2024		2023
Stock options	$	7.7	$	9.1	$	22.5	$	29.4
RSUs	7.2		5.4		20.2		14.7
Warrant shares	2.0		0.9		4.5		1.5
Total stock-based compensation expense	$	16.9	$	15.4	$	47.2	$	45.6