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Stock-based Compensation (Tables) | 9 Months Ended | 12 Months Ended
--- | --- | ---
Sep. 30, 2020 | Dec. 31, 2019
Stock-based Compensation |  |
Fair value assumptions | The fair value of each option granted for the nine months ended September 30, 2020 and 2019 is estimated on the date of grant using the Black-Scholes model based on the following assumptions: ​
​ | ​ | ​ | ​ | ​ | ​
​ |  | Nine Months Ended |
​ | ​ | September 30, |
​ | ​ | 2020 | ​ | 2019 | ​
Weighted average expected term (years) |  | 6.1 |  | 6.1 | ​
Risk-free interest rate |  | 0.8 | % | 1.7 | %
Volatility |  | 40 | % | 45 | %
Expected dividend yield |  | 0 | % | 0 | %
| The fair value of each option granted during the year ended December 31, 2018 and 2019 is estimated on the date of grant using the Black-Scholes model with the following assumptions (annualized percentage): ​
​ | ​ | ​ | ​ | ​ | ​
​ | ​ | December 31, |
​ |  | 2018 |  | 2019 |
Weighted average expected term (years) |  | 6.07 |  | 6.06 | ​
Risk‑free interest rate |  | 2.6% ‑ 3.1 | % | 1.3% ‑ 2.5 | %
Volatility |  | 50 | % | 45 | %
Expected dividend yield |  | 0 | % | 0 | %
Stock options activity | The following table summarizes activity of stock options ($ in millions, except for option and average amounts): ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ |  |  |  |  | ​ |  | Weighted- |  |  | ​
​ | ​ | ​ | ​ | Weighted- | ​ | Average | ​ | ​ | ​
​ | ​ | ​ | ​ | Average | ​ | Remaining | ​ | Aggregate
​ | ​ | Number of | ​ | Exercise | ​ | Contractual | ​ | Intrinsic
​ |  | Options |  | Price |  | Term (Years) |  | Value
Outstanding as of December 31, 2019 |  | 4,048,802 | ​ | $ | 13.27 |  | 8.8 | ​ | $ | 42.2
Granted |  | 968,280 | ​ |  | 30.44 |  |  | ​ |  |
Exercised |  | (92,157) | ​ |  | 3.77 |  |  | ​ |  |
Cancelled |  | (110,001) | ​ |  | 20.87 |  |  | ​ |  |
Outstanding as of September 30, 2020 |  | 4,814,924 | ​ | $ | 16.73 |  | 8.4 | ​ | $ | 158.8
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
Options exercisable as of September 30, 2020 |  | 1,698,568 | ​ | $ | 8.72 |  | 7.5 | ​ | $ | 69.6
Options vested and expected to vest as of September 30, 2020 |  | 4,814,924 | ​ | $ | 16.73 |  | 8.4 | ​ | $ | 158.8
| The following table summarizes activity under the 2015 Plan of stock options granted ($ in millions, except for option and average amounts): ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | Weighted‑ | ​ | ​ | ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | Average | ​ | ​ | ​
​ | ​ | ​ | ​ | Weighted‑ | ​ | Remaining | ​ | ​ | ​
​ | ​ | ​ | ​ | Average | ​ | Contractual | ​ | Aggregate
​ | ​ | Number of | ​ | Exercise | ​ | Term | ​ | Intrinsic
​ |  | Options |  | Price |  | (Years) |  | Value
Outstanding as of December 31, 2018 |  | 2,169,000 | ​ | $ | 3.62 |  | 8.75 | ​ | $ | 17.3
Granted |  | 2,255,800 | ​ |  | 21.17 |  | 9.40 | ​ |  |
Exercised |  | (182,057) | ​ |  | 1.73 |  |  | ​ |  |
Cancelled |  | (193,941) | ​ |  | 7.99 |  |  | ​ |  |
Outstanding as of December 31, 2019 |  | 4,048,802 | ​ | $ | 13.27 |  | 8.83 | ​ | $ | 42.2
Options exercisable as of December 31, 2019 |  | 987,985 | ​ | $ | 4.00 |  | 7.52 | ​ | $ | 19.5
Options unvested as of December 31, 2019 |  | 3,110,817 | ​ | $ | 16.39 |  | 9.25 | ​ | $ | 22.7
Stock-based compensation expense | Stock-based compensation expense was classified in the condensed consolidated statements of operations as follows ($ in millions): ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ |  | Three Months Ended |  | Nine Months Ended
​ | ​ | September 30, | ​ | September 30,
​ |  | 2020 |  | 2019 |  | 2020 |  | 2019
Loss and loss adjustment expense, net | ​ | $ | 0.1 | ​ | $ | — | ​ | $ | 0.2 | ​ | $ | —
Other insurance expense | ​ |  | 0.1 | ​ |  | 0.2 | ​ |  | 0.5 | ​ |  | 0.4
Sales and marketing | ​ |  | 0.8 | ​ |  | 0.3 | ​ |  | 2.1 | ​ |  | 0.5
Technology development | ​ |  | 0.8 | ​ |  | 0.7 | ​ |  | 2.1 | ​ |  | 0.8
General and administrative | ​ |  | 0.9 | ​ |  | 0.3 | ​ |  | 2.4 | ​ |  | 0.6
Total stock-based compensation expense | ​ | $ | 2.7 | ​ | $ | 1.5 | ​ | $ | 7.3 | ​ | $ | 2.3
| Stock-based compensation expense was classified in the consolidated statements of operations and comprehensive loss as follows ($ in millions): ​
​ | ​ | ​ | ​ | ​ | ​ | ​
​ | ​ | Year Ended
​ | ​ | December 31,
​ | ​ | 2018 | ​ | 2019
Other insurance expense |  | $ | 0.2 |  | $ | 0.6
Sales and marketing | ​ |  | 0.3 | ​ |  | 1.1
Technology development | ​ |  | 0.1 | ​ |  | 1.4
General and administrative | ​ |  | 1.5 | ​ |  | 1.2
Total stock‑based compensation expense | ​ | $ | 2.1 | ​ | $ | 4.3

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