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

September 30, 2022December 31, 2021
Stock options issued and outstanding3,309,305 4,019,011 
Restricted stock units outstanding11,322,125 4,617,425 
Shares available for future equity grants12,774,103 15,205,854 
Total shares reserved for future issuance27,405,533 23,842,290 
We have reserved shares of common stock for future issuance under our ESPP as follows:

Nine Months Ended September 30, 2022Year Ended December 31, 2021
Shares available for issuance at beginning of period4,768,5064,039,667
Shares issued during the period(661,054)(334,248)
Total shares available for future issuance at end of period4,107,4523,705,419
Schedule of Stock Option Activity Option activity for the nine months ended September 30, 2022 was as follows:
Number of OptionsWeighted-Average Exercise PriceWeighted-Average Remaining Contractual Life (Years)Aggregate Intrinsic Value
Outstanding as of January 1, 2022(1)
4,019,011$8.02 3.73$122,038 
PSOs earned(1)
150,00027.50 
Options exercised(695,705)6.96 
Options expired(164,001)9.06 
Outstanding as of September 30, 2022
3,309,3059.08 3.182,405 
Options exercisable as of September 30, 2022
3,309,3059.08 3.182,405 
(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.
Schedule of Nonvested Restricted Stock Units Activity Restricted stock unit activity for the nine months ended September 30, 2022 was as follows:
Restricted Stock UnitsWeighted-Average Grant-Date Fair Value
Outstanding as of January 1, 20224,617,425 $37.13 
Granted9,866,403 10.53 
Vested(1,362,071)28.05 
Forfeited or canceled(1,799,632)25.94 
Outstanding or deferred as of September 30, 2022(1)
11,322,125 16.82 
(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, 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 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-based compensation expense associated with the PSUs is as follows:
Three Months Ended September 30,Nine Months Ended September 30,
2022202120222021
PSU expense$1,867 $1,844 $3,536 $4,465 
Expense due to reassessment of achievement related to prior periods(815)— (815)— 
Total expense$1,052 $1,844 $2,721 $4,465 
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:
Three Months Ended September 30,Nine Months Ended September 30,
2022202120222021
Cost of revenue$4,387 $3,283 $11,644 $10,019 
Technology and development(1)
7,371 5,455 23,036 16,987 
Marketing1,028 537 3,024 1,615 
General and administrative5,284 3,835 13,968 10,817 
Total stock-based compensation$18,070 $13,110 $51,672 $39,438 
(1) Net of $930 and $1,028 of stock-based compensation that was capitalized in the three months ended September 30, 2022 and 2021, respectively, and $2,983 and $2,745 for the nine months ended September 30, 2022 and 2021, respectively.