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Equity and Equity Compensation Plans (Tables)
 12 Months Ended
Dec. 31, 2020
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,
20202019
Stock options issued and outstanding5,733,738 7,792,181 
Restricted stock units outstanding4,459,743 5,023,412 
Shares available for future equity grants11,309,377 7,100,499 
Total shares reserved for future issuance21,502,858 19,916,092 
We have reserved shares of common stock for future issuance under our ESPP as follows:
December 31,
20202019
Shares available for issuance at beginning of period3,330,271 2,890,973 
Shares issued during the period(320,609)(490,717)
     Total shares available for issuance at end of period 3,009,662 2,400,256
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, 2020For the Offering Period beginning January 1, 2020
Expected life0.5 years0.5 years
Volatility101.06%43.65%
Risk-free interest rate0.17%1.57%
Dividend yield—%—%
Weighted-average grant date fair value$17.48$5.77
Schedule of Stock Option Activity Option activity for the year ended December 31, 2020 was as follows:
Number Of OptionsWeighted- Average Exercise PriceWeighted Average Remaining Contractual Life (years)Aggregate Intrinsic Value
Outstanding at January 1, 20207,792,181 $7.00 5.28$111,122 
Options exercised(2,011,938)6.31 
Options forfeited (36,206)9.13 
Options canceled(10,299)8.98 
Outstanding at December 31, 20205,733,738 $7.23 4.39$352,076 
Options exercisable at December 31, 20205,520,083 $6.63 4.26$342,225 
Schedule of Share-based Compensation, Restricted Stock Units Award Activity Restricted stock unit activity for the year ended December 31, 2020 was as follows:
Restricted Stock UnitsWeighted Average Grant-Date Fair Value
Outstanding at January 1, 20205,023,412 $18.69 
Granted1,658,632 43.01 
Vested(1,490,506)19.12 
Forfeited or canceled(731,795)19.56 
Outstanding or deferred at December 31, 2020(1)
4,459,743 $27.44 

(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, 2020 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:
Year Ended December 31,
202020192018
Expense associated with the current period$2,664 $894 $610 
Expense due to reassessment of achievement related to prior periods190 (610)— 
Total expense$2,854 $284 $610 
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,
202020192018
Cost of revenue$8,844 $6,087 $5,567 
Technology and development(1)
16,564 12,362 7,576 
Marketing1,569 1,418 662 
General and administrative9,996 7,947 6,633 
Total stock-based compensation$36,973 $27,814 $20,438 

(1) Net of $2,348, $1,280 and $522 of stock-based compensation expense capitalized for internally developed software for the years ended December 31, 2020, 2019 and 2018, respectively.
Disclosure of Share-based Compensation Arrangements by Share-based Payment Award
The fair value of stock option awards was estimated at the grant date with the following weighted average assumptions:
December 31,
202020192018
Expected life06.5 years0
Volatility—%33.76%—%
Risk-free interest rate—%2.12%—%
Dividend yield—%—%—%
Weighted-average grant date fair value
$—$3.22$—
The fair value of stock options vested and the intrinsic value of stock options exercised are as follows:
Year Ended December 31,
202020192018
Fair value of options vested$2,228 $4,747 $7,089 
Intrinsic value of options exercised55,822 20,811 49,276