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Equity and Equity Compensation Plans (Tables)
 9 Months Ended
Sep. 30, 2021
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:

September 30, 2021December 31, 2020
Stock options issued and outstanding4,374,257 5,733,738 
Restricted stock units outstanding3,452,462 4,459,743 
Shares available for future equity grants16,718,941 11,309,377 
Total shares reserved for future issuance24,545,660 21,502,858 
We have reserved shares of common stock for future issuance under our ESPP as follows:

Nine Months Ended September 30, 2021Year Ended December 31, 2020
Shares available for issuance at beginning of period4,039,6673,330,271
Shares issued during the period(135,426)(320,609)
Total shares available for future issuance at end of period3,904,2413,009,662
Schedule of Stock Option Activity Option activity for the nine months ended September 30, 2021 was as follows:
Number of OptionsWeighted-Average Exercise PriceWeighted-Average Remaining Contractual Life (Years)Aggregate Intrinsic Value
Outstanding as of January 1, 20215,733,738$7.23 4.39$352,076 
Options exercised(1,354,078)5.10 
Options forfeited(290)10.80 
Options expired(5,113)10.80 
Outstanding as of September 30, 2021
4,374,2577.88 3.92184,685 
Options exercisable as of September 30, 2021
4,224,2577.18 3.78181,295 
Schedule of Nonvested Restricted Stock Units Activity Restricted stock unit activity for the nine months ended September 30, 2021 was as follows:
Restricted Stock UnitsWeighted-Average Grant-Date Fair Value
Outstanding as of January 1, 20214,459,743 $27.44 
Granted658,610 55.89 
Vested(1)
(1,072,378)22.39 
Forfeited or canceled(593,513)26.42 
Outstanding or deferred as of September 30, 2021(1)
3,452,462 34.62 

(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 has been deferred. The amount reported as outstanding or deferred as of September 30, 2021 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 basic and diluted weighted shares outstanding used to calculate net (loss) income 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:
Nine Months Ended September 30,
20212020
Expense associated with the current period$4,465 $(610)
Expense due to reassessment of achievement related to prior periods— 484 
Total expense$4,465 $(126)
The following table details, for each period indicated, our stock-based compensation, net of forfeitures, and the amount capitalized in website and software development costs, each as included in our consolidated statements of comprehensive (loss) income:
Three Months Ended September 30,Nine Months Ended September 30,
2021202020212020
Cost of revenue$3,283 $2,574 $10,019 $5,981 
Technology and development (1)
5,455 4,964 16,987 11,736 
Marketing537 403 1,615 1,130 
General and administrative3,835 3,407 10,817 6,917 
Total stock-based compensation$13,110 $11,348 $39,438 $25,764 
(1) Net of $1,028 and $563 of stock-based compensation that was capitalized in the three months ended September 30, 2021 and 2020, respectively, and $2,745 and $1,714 for the nine months ended September 30, 2021 and 2020.