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Stock-based Compensation (Tables) | 12 Months Ended
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Dec. 31, 2022
Summary of Stock Option Activity | The following table summarizes the stock option activity during the year ended December 31, 2022 (aggregate intrinsic value in thousands):
|  |  |  |  |  |  |  |  |  | Weighted- |  |  |  |  |
|  |  |  |  |  | Weighted- |  |  | Average |  |  |  |  |
|  |  |  |  |  | Average |  |  | Remaining |  |  | Aggregate |
|  | Number of Shares |  |  | Exercise Price |  |  | Contractual Life |  |  | Intrinsic Value |
Outstanding at December 31, 2021 |  |  | 7,642,690 |  |  | $ | 12.98 |  |  |  | 6.1 |  |  | $ | 511,979 |
Exercised |  |  | (1,716,286 | ) |  |  | 13.00 |  |  |  |  |  |  |  | 75,066 |
Canceled/Forfeited |  |  | (202,632 | ) |  |  | 22.02 |  |  |  |  |  |  |  |  |
Outstanding at December 31, 2022 |  |  | 5,723,772 |  |  |  | 12.65 |  |  |  | 5.2 |  |  |  | 197,620 |
Exercisable at December 31, 2022 |  |  | 5,491,335 |  |  | $ | 12.20 |  |  |  | 5.1 |  |  | $ | 192,073 |
Summary of Activity in Connection with RSUs | The following table summarizes the RSU activity during the year ended December 31, 2022:
|  | Number of Shares |  |  | Weighted-Average Grant Date Fair Value |
Unvested at December 31, 2021 |  |  | 6,622,684 |  |  | $ | 59.72 |
Granted |  |  | 5,859,110 |  |  |  | 55.71 |
Vested |  |  | (2,845,174 | ) |  |  | 57.14 |
Canceled/Forfeited |  |  | (1,141,322 | ) |  |  | 58.80 |
Unvested at December 31, 2022 |  |  | 8,495,298 |  |  | $ | 57.94 |
Summary of Total Stock-based Compensation Cost from Stock Options, RSUs, ESPP, RSAs, and Sales of Stock | The Company recorded total stock-based compensation cost from stock options, RSUs, ESPP, RSAs, and sales of stock by employees in excess of fair value as follows (in thousands):
|  | Year Ended December 31, |
|  | 2022 |  |  | 2021 |  |  | 2020 |
Cost of revenue |  | $ | 7,253 |  |  | $ | 8,094 |  |  | $ | 1,722 |
Sales and marketing |  |  | 53,397 |  |  |  | 68,755 |  |  |  | 13,385 |
Research and development |  |  | 63,262 |  |  |  | 85,040 |  |  |  | 12,930 |
General and administrative |  |  | 38,974 |  |  |  | 65,272 |  |  |  | 15,923 |
Total stock-based compensation expense |  | $ | 162,886 |  |  | $ | 227,161 |  |  | $ | 43,960 |
Stock-based compensation capitalized for software development and cloud-computing arrangement implementation costs |  |  | 8,818 |  |  |  | 5,247 |  |  |  | 575 |
Total stock-based compensation cost |  | $ | 171,704 |  |  | $ | 232,408 |  |  | $ | 44,535 |
Employee Stock Purchase Plan |
Schedule of Fair Value of ESPP Purchase Rights on Date of Grant | The fair value of the ESPP purchase rights on the date of grant using the Black-Scholes option pricing model was estimated using the following assumptions:
|  | December 31,
|  | 2022 |  | 2021
Risk-free interest rate |  | 1.47% to 4.55% |  | 0.03% to 0.18%
Expected term (in years) |  | 0.5 to 1.0 |  | 0.5 to 1.5
Estimated dividend yield |  | 0.00% |  | 0.00%
Estimated weighted-average volatility |  | 61.14% to 72.69% |  | 44.81% to 69.39%

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