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Stock-based Compensation (Tables) | 9 Months Ended
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Sep. 30, 2023
Share-Based Payment Arrangement [Abstract] |
Fair value assumptions | The fair value of each option granted for the nine months ended September 30, 2023 and 2022 is estimated on the date of grant using the Black-Scholes model based on the following assumptions:
|  | Nine Months Ended September 30,
|  | 2023 |  | 2022
Weighted average expected term (years) |  | 6.0 |  | 6.1
Risk-free interest rate |  | 4.2% |  | 2.7%
Volatility |  | 74% |  | 47%
Expected dividend yield |  | 0% |  | 0%
Stock options activity | The following tables summarize activity of stock options and restricted stock units ("RSUs") ($ in millions, except for number of options and weighted average amounts): Stock options
|  | Number of Options |  | Weighted- Average Exercise Price |  | Weighted-Average Remaining Contractual Term (Years) |  | Aggregate Intrinsic Value
Outstanding as of December 31, 2022 (1) |  | 9,760,657 |  | $ | 39.43 |  |  | 8.17 |  | $ | 8.05 |
Granted |  | 1,016,218 |  |  | 15.67 |  |  |  |  |
Exercised |  | (92,954) |  |  | 5.13 |  |  |  |  |
Cancelled/Forfeited |  | (961,442) |  |  | 38.87 |  |  |  |  |
Outstanding as of September 30, 2023 |  | 9,722,479 |  | $ | 37.28 |  |  | 7.47 |  | $ | 5.30 |
Options exercisable as of September 30, 2023 |  | 4,386,472 |  | $ | 29.79 |  |  | 6.22 |  | $ | 5.30 |
Options unvested as of September 30, 2023 |  | 5,336,007 |  | $ | 43.44 |  |  | 8.49 |  | $ | — |
(1) Includes assumed options of 72,410 from the Metromile Acquisition (see Note 5).
Restricted stock units activity | Restricted Stock Units
|  | Number of Shares |  | Weighted Average Grant Date Fair Value
Outstanding as of December 31, 2022 (1) |  | 1,651,243 |  |  | $ | 27.92 |
Granted |  | 2,753,356 |  |  | 15.84 |
Vested |  | (541,372) |  |  | 25.28 |
Cancelled/Forfeited |  | (523,455) |  |  | 22.38 |
Outstanding as of September 30, 2023 |  | 3,339,772 |  |  | $ | 19.22 |
(1) Includes assumed restricted stock units of 331,797 from the Metromile Acquisition (see Note 5).
Stock-based compensation expense | Stock-based compensation expense from stock options and RSUs granted are included and classified in the condensed consolidated statements of operations for the three and nine months ended September 30, 2023 and 2022, including assumed awards from the Metromile Acquisition and warrant shares for the three and nine months ended September 30, 2023 and 2022, as follows ($ in millions):
|  | Three Months Ended September 30, |  | Nine Months Ended September 30,
|  | 2023 |  | 2022 |  | 2023 |  | 2022
Loss and loss adjustment expense, net |  | $ | 0.8 |  |  | $ | 0.7 |  |  | $ | 2.2 |  |  | $ | 1.9 |
Other insurance expense |  | 0.6 |  |  | 0.4 |  |  | 1.6 |  |  | 1.2 |
Sales and marketing (1) |  | 1.9 |  |  | 1.8 |  |  | 4.6 |  |  | 5.0 |
Technology development |  | 6.4 |  |  | 6.4 |  |  | 19.4 |  |  | 17.6 |
General and administrative |  | 5.7 |  |  | 6.3 |  |  | 17.8 |  |  | 17.9 |
Total stock-based compensation expense |  | $ | 15.4 |  |  | $ | 15.6 |  |  | $ | 45.6 |  |  | $ | 43.6 |
(1) Includes compensation expense related to warrant shares of $0.9 million and $1.5 million for the three and nine months ended September 30, 2023. Stock-based compensation expense classified by award type as included in the condensed consolidated statements of operations is as follows ($ in millions):
|  | Three Months Ended September 30, |  | Nine Months Ended September 30,
|  | 2023 |  | 2022 |  | 2023 |  | 2022
Stock options |  | $ | 9.1 |  |  | $ | 11.9 |  |  | $ | 29.4 |  |  | $ | 35.9 |
RSUs |  | 5.4 |  |  | 3.7 |  |  | 14.7 |  |  | 7.7 |
Warrant shares |  | 0.9 |  |  | — |  |  | 1.5 |  |  | — |
Total stock-based compensation expense |  | $ | 15.4 |  |  | $ | 15.6 |  |  | $ | 45.6 |  |  | $ | 43.6 |

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