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Equity and Equity Compensation Plans (Tables)
 12 Months Ended
Dec. 31, 2022
Share-Based Payment Arrangement [Abstract]  
Schedule of Reserved Shares of Common Stock
We have reserved shares of common stock for future issuance under our 2017 EIP as follows:
December 31,
20222021
Stock options issued and outstanding3,282,789 4,019,011 
Restricted stock units outstanding15,731,632 4,617,425 
Shares available for future equity grants7,951,616 15,205,854 
Total shares reserved for future issuance26,966,037 23,842,290 
We have reserved shares of common stock for future issuance under our ESPP as follows:
December 31,
20222021
Shares available for issuance at beginning of period5,865,467 4,039,667 
Shares issued during the period(1,170,106)(334,248)
     Total shares available for issuance at end of period 4,695,361 3,705,419
Schedule of Valuation Assumptions
The weighted-average grant date fair value and the assumptions used in calculating fair values of shares forecasted to be issued pursuant to our ESPP are as follows:
For the Offering Period beginning July 1, 2022For the Offering Period beginning January 1, 2022
Expected life0.5 years0.5 years
Volatility95.48%53.94%
Risk-free interest rate2.52%0.22%
Dividend yield—%—%
Weighted-average grant date fair value$3.35$11.52
Schedule of Stock Option Activity Option activity for the year ended December 31, 2022 was as follows:
Number Of OptionsWeighted-Average Exercise PriceWeighted-Average Remaining Contractual Life (years)Aggregate Intrinsic Value
Outstanding at January 1, 20224,019,011 $8.02 3.73$122,038 
PSOs earned(1)
150,000 27.50 
Options exercised(700,333)6.94 
Options expired(185,889)8.89 
Outstanding at December 31, 2022
3,282,789 $9.10 2.90$1,145 
Options exercisable at December 31, 2022
3,282,789 $9.10 2.90$1,145 
(1) We granted stock options subject to performance conditions (“PSOs”) to our chief executive officer in 2019. We previously reported the target achievement level of these PSOs - 150,000 PSOs - within our outstanding stock options. During the first quarter of 2022, our board of directors determined that our chief executive officer earned his PSOs at the maximum achievement level. Accordingly, we are reporting an additional 150,000 PSOs as being earned during the first quarter of 2022.
Disclosure of Share-based Compensation Arrangements by Share-based Payment Award
The fair value of stock options vested and the intrinsic value of stock options exercised are as follows:
Year Ended December 31,
202220212020
Fair value of options vested$484 $793 $2,228 
Intrinsic value of options exercised5,588 90,920 55,822 
Schedule of Share-based Compensation, Restricted Stock Units Award Activity Restricted stock unit activity for the year ended December 31, 2022 was as follows:
Restricted Stock UnitsWeighted-Average Grant Date Fair Value
Outstanding at January 1, 20224,617,425 $37.13 
Granted16,408,296 8.54 
Vested(1,972,441)30.43 
Forfeited or canceled(3,321,648)21.13 
Outstanding or deferred at December 31, 2022(1)
15,731,632 $11.53 
(1) Starting with the restricted stock units granted to them in June 2019, our non-employee directors have the option to defer the issuance of common stock receivable upon vesting of such restricted stock units until 60 days following the day they are no longer providing services to us or, if earlier, upon a change in control transaction. The amount reported as vested excludes restricted stock units that have vested but whose settlement into shares have been deferred. The amount reported as outstanding or deferred as of December 31, 2022 includes these restricted stock units. As no further conditions exist to prevent the issuance of the shares of common stock underlying these restricted stock units, the shares are included in the basic and diluted weighted shares outstanding used to calculate net loss per share attributable to common stock. The amount of shares whose issuance have been deferred is not considered material and is not reported separately from stock-based compensation in our consolidated statements of changes in mezzanine equity and stockholders’ equity.
Schedule of Allocation of Share-based Compensation Costs Stock-compensation expense associated with the PSUs is as follows:
Year Ended December 31,
202220212020
Expense associated with the current period$5,341 $6,314 $2,664 
Expense due to reassessment of achievement related to prior periods(267)— 190 
Total expense$5,074 $6,314 $2,854 
The following table details, for each period indicated, (i) our stock-based compensation net of forfeitures, and the amount capitalized in internally developed software and (ii) includes changes to the probability of achieving outstanding performance-based equity awards, each as included in our consolidated statements of comprehensive loss:
Year Ended December 31,
202220212020
Cost of revenue$15,950 $13,614 $8,844 
Technology and development(1)
29,608 23,275 16,564 
Marketing4,093 2,350 1,569 
General and administrative18,606 15,483 9,996 
Total stock-based compensation$68,257 $54,722 $36,973 
(1) Net of $3,660, $4,059 and $2,348 of stock-based compensation expense capitalized for internally developed software for the years ended December 31, 2022, 2021 and 2020, respectively.