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Stockholders’ Equity (Tables)

12 Months Ended

Dec. 31, 2023

Equity [Abstract]

Schedule of 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 January 1, 2022			1,901,163						$	33.05					8.3						$	84.8
Granted			625,578						45.07												—
Exercised			(145,525)						13.80												3.7
Cancelled/Expired			(394,328)						41.61												2.2
Outstanding as of December 31, 2022			1,986,978						$	36.54					7.8						$	1.3
Granted			—						—
Exercised			(103,047)						11.89												0.5
Cancelled/Expired			(294,402)						24.07												0.2
Outstanding as of December 31, 2023			1,589,529						$	16.13					6.8						$	0.2
Vested and exercisable as of December 31, 2023			1,386,891						$	16.16					6.7						$	0.2

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:

									December 31,
									2022
Expected term (in years)									5.0 - 6.7
Expected volatility									29.6% - 30.9%
Risk-free interest rate									2.7% - 3.0%
Expected dividend yield									—		%

Schedule of Share-based Payment Award, Restricted Stock Units and 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:

			December 31,
			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 years ended December 31, 2023 and 2022:

			Number of Shares						Weighted Average Grant-Date Fair Value per Share
Unvested and outstanding as of December 31, 2021			1,165,571						$	99.85
Granted			2,829,774						30.49
Vested			(444,105)						87.10
Canceled and forfeited			(669,256)						67.89
Unvested and outstanding as of December 31, 2022			2,881,984						$	41.15
Granted			1,579,871						16.89
Vested			(1,139,308)						39.41
Canceled and forfeited			(787,864)						36.26
Unvested and outstanding as of December 31, 2023			2,534,683						$	28.28

Schedule of 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):

									Year Ended
									December 31,
															2023						2022
Losses and loss adjustment expenses															$	1.2					$	2.6
Insurance related expenses															4.9						5.4
Technology and development															12.5						19.2
Sales and marketing															13.1						13.7
General and administrative															25.8						21.0
Total stock-based compensation expense															$	57.5					$	61.9

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