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Equity and Equity Compensation Plans (Tables)
 6 Months Ended
Jun. 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:

June 30, 2021December 31, 2020
Stock options issued and outstanding4,639,132 5,733,738 
Restricted stock units outstanding3,699,318 4,459,743 
Shares available for future equity grants16,711,246 11,309,377 
Total shares reserved for future issuance25,049,696 21,502,858 
We have reserved shares of common stock for future issuance under our ESPP as follows:

Six Months Ended June 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 six months ended June 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(1,089,203)4.77 
Options forfeited(290)10.80 
Options expired(5,113)10.80 
Outstanding as of June 30, 20214,639,1327.80 4.18257,994 
Options exercisable as of June 30, 20214,489,1327.14 4.05252,608 
Schedule of Nonvested Restricted Stock Units Activity Restricted stock unit activity for the six months ended June 30, 2021 was as follows:
Restricted Stock UnitsWeighted-Average Grant-Date Fair Value
Outstanding as of January 1, 20214,459,743 $27.44 
Granted407,853 59.67 
Vested(1)
(737,403)22.04 
Forfeited or canceled(430,875)24.82 
Outstanding or deferred as of June 30, 2021(1)
3,699,318 $32.38 

(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 June 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 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:
Six Months Ended June 30,
20212020
Expense associated with the current period$2,621 $336 
Expense due to reassessment of achievement related to prior periods— (494)
Total expense$2,621 $(158)
The following table details, for each period indicated, our stock-based compensation, net of forfeitures, and the amount capitalized in internally developed software, each as included in our consolidated statements of comprehensive loss:
Three Months Ended June 30,Six Months Ended June 30,
2021202020212020
Cost of revenue$3,758 $1,769 $6,736 $3,407 
Technology and development (1)
5,771 3,124 11,532 6,772 
Marketing535 352 1,078 727 
General and administrative3,679 1,960 6,981 3,510 
Total stock-based compensation$13,743 $7,205 $26,327 $14,416 
(1) Net of $985 and $647 of stock-based compensation that was capitalized in the three months ended June 30, 2021 and 2020, respectively, and $1,717 and $1,151 for the six months ended June 30, 2021 and 2020,