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Stock-based Compensation (Tables)

12 Months Ended

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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- Definition

Tabular disclosure of allocation of amount expensed and capitalized for award under share-based payment arrangement to statement of income or comprehensive income and statement of financial position. Includes, but is not limited to, corresponding line item in financial statement.

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