Stock-based Compensation (Tables)

6 Months Ended

Jun. 30, 2026

Share-Based Payment Arrangement [Abstract]

Schedule of Fair Value Assumptions

The fair value of each option granted during the six months ended June 30, 2026 and 2025 is estimated on the date of grant using the Black-Scholes model based on the following assumptions:

	Six Months Ended June 30,
	2026	2025
Weighted average expected term (years)	6.9	6.0
Risk-free interest rate	3.9%	4.1%
Volatility	80%	79%
Expected dividend yield	0%	0%

Summarized in the table below are the assumptions used in determining the grant-date fair value of $42.80 using the Monte-Carlo simulation approach for the RSUs with market condition:

Expected term (years)	2.0
Risk-free interest rate	3.7	%
Volatility	81	%
Expected dividend yield	0	%

Schedule of Stock Options Activity

The following tables summarize activity of stock options and restricted stock units:

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, 2025	7,253,851	$	30.76	6.39	$	302.9
Granted	64,507	$	56.20
Exercised	(481,371)	$	12.59
Canceled/Forfeited	(50,450)	$	70.45
Outstanding as of June 30, 2026	6,786,537	$	32.00	6.25	$	236.3
Options exercisable as of June 30, 2026	5,610,451	$	31.30	5.84	$	201.3
Options unvested as of June 30, 2026	1,176,086	$	35.32	8.22	$	35.0

Schedule of Restricted Stock Units Activity

Restricted Stock Units with service condition

	Number of Shares	Weighted Average Grant Date Fair Value
Outstanding as of December 31, 2025	3,196,072	$	29.98
Granted	3,216,149	$	58.30
Vested	(938,132)	$	27.04
Canceled/Forfeited	(149,336)	$	31.99
Outstanding as of June 30, 2026	5,324,753	$	47.59

Schedule of Stock-Based Compensation Expense

Stock-based compensation expense from stock options, Restricted Stock Units with service condition ("RSUs with service condition") and RSUs with market condition, including equity awards from the Assumed Plans as discussed above and warrants (Note 10), were included and presented in the condensed consolidated statements of operations and comprehensive loss as follows ($ in millions):

	Three Months Ended June 30,				Six Months Ended June 30,
	2026		2025		2026		2025
Loss and loss adjustment expense, net	$	0.6	$	0.6	$	1.2	$	1.1
Other insurance expense	0.8		0.6		1.5		1.3
Sales and marketing (1)	1.0		0.8		2.1		(3.5)
Technology development (2)	9.8		6.9		18.7		13.7
General and administrative (2)	12.3		6.5		22.2		13.1
Total stock-based compensation expense	$	24.5	$	15.4	$	45.7	$	25.7

(1) Includes the impact of the canceled unvested warrant shares for contract year 2 related to the termination of the Warrant Agreement with Chewy in the amount of $5.2 million for the six months ended June 30, 2025.

(2) Includes $1.9 million and $2.5 million of compensation expense related to the RSUs with market condition for the three and six months ended June 30, 2026.

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

	Three Months Ended June 30,				Six Months Ended June 30,
	2026		2025		2026		2025
Stock options	$	5.2	$	5.8	$	11.6	$	12.3
RSUs with service condition	17.4		9.6		31.6		18.6
RSUs with market condition	1.9		—		2.5		—
Warrant shares	—		—		—		(5.2)
Total stock-based compensation expense	$	24.5	$	15.4	$	45.7	$	25.7