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Stock-based Compensation (Tables) | 12 Months Ended
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Dec. 31, 2025
Share-Based Payment Arrangement [Abstract] |
Schedule of Fair value assumptions | The fair value of each option granted during the years ended December 31, 2025 and 2024 is estimated on the date of grant using the Black-Scholes model with the following assumptions:
| December 31,
| 2025 |  | 2024
Weighted average expected term (years) | 5.8 |  | 5.8
Risk-free interest rate | 4.0% |  | 4.1%
Volatility | 81% |  | 77%
Expected dividend yield | 0% |  | 0%
Schedule of Stock options activity | The following tables summarize activity of stock options and restricted stock units (“RSU’s”): 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, 2024 | 9,376,193 |  |  | $ | 36.03 |  |  | 6.81 |  | $ | 106.8 |
Granted | 608,928 |  |  | $ | 58.31 |  |  |  |  |
Exercised | (1,346,225) |  |  | $ | 23.73 |  |  |  |  |
Canceled/forfeited | (1,385,045) |  |  | $ | 85.55 |  |  |  |  |
Outstanding as of December 31, 2025 | 7,253,851 |  |  | $ | 30.76 |  |  | 6.39 |  | $ | 302.9 |
Options exercisable as of December 31, 2025 | 5,295,891 |  |  | $ | 30.71 |  |  | 5.74 |  | $ | 224.0 |
Options unvested as of December 31, 2025 | 1,957,960 |  |  | $ | 30.91 |  |  | 8.15 |  | $ | 78.9 |
Schedule of Restricted stock units | Restricted Stock Units
| Number of shares |  | Grant Date Fair Value
Outstanding as of December 31, 2024 | 4,278,383 |  |  | $ | 20.00 |
Granted | 1,189,864 |  |  | $ | 49.90 |
Vested | (1,840,124) |  |  | $ | 21.62 |
Canceled/forfeited | (432,051) |  |  | $ | 21.59 |
Outstanding as of December 31, 2025 | 3,196,072 |  |  | $ | 29.98 |
Schedule of 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 15), were included and presented in the consolidated statements of operations and comprehensive income (loss) as follows ($ in millions):
| December 31,
| 2025 |  | 2024 |  | 2023
Loss and loss adjustment expense, net | $ | 2.3 |  |  | $ | 2.1 |  |  | $ | 2.8 |
Other insurance expense | 2.9 |  |  | 2.5 |  |  | 2.2 |
Sales and marketing (1) | (1.5) |  |  | 10.6 |  |  | 6.4 |
Technology development | 29.1 |  |  | 26.2 |  |  | 25.7 |
General and administrative | 28.5 |  |  | 23.1 |  |  | 22.8 |
Total stock-based compensation expense | $ | 61.3 |  |  | $ | 64.5 |  |  | $ | 59.9 |
(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 year ended December 31, 2025, and compensation expense related to warrant shares of $6.5 million and $2.5 million for the years ended December 31, 2024 and 2023. Stock-based compensation expense classified by award type as included in the consolidated statements of operations and comprehensive income (loss) is as follows ($ in millions):
| December 31,
| 2025 |  | 2024 |  | 2023
Stock options | $ | 25.2 |  |  | $ | 29.8 |  |  | $ | 37.6 |
RSUs | 41.3 |  |  | 28.2 |  |  | 19.8 |
Warrant shares | (5.2) |  |  | 6.5 |  |  | 2.5 |
Total stock-based compensation expense | $ | 61.3 |  |  | $ | 64.5 |  |  | $ | 59.9 |

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- Definition Tabular disclosure of the significant assumptions used during the year to estimate the fair value of stock options, including, but not limited to: (a) expected term of share options and similar instruments, (b) expected volatility of the entity's shares, (c) expected dividends, (d) risk-free rate(s), and (e) discount for post-vesting restrictions. + References Reference 1: http://fasb.org/us-gaap/role/ref/legacyRef -Topic 718 -SubTopic 10 -Subparagraph (f)(2) -Name Accounting Standards Codification -Paragraph 2 -Section 50 -Publisher FASB -URI https://asc.fasb.org/1943274/2147480429/718-10-50-2 + Details
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