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Stockholders’ Equity (Tables) | 12 Months Ended
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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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