Equity and Equity Compensation Plans | Equity and Equity Compensation Plans Common Stock —As of June 30, 2020 and December 31, 2019, our amended and restated certificate of incorporation authorized us to issue 500,000,000 shares of common stock with a par value of $0.001 per share. Preferred Stock — As of June 30, 2020 and December 31, 2019 , our amended and restated certificate of incorporation authorized us to issue 10,000,000 shares of preferred stock with a par value of $0.001. Amended and Restated 2004 Equity Incentive Plan — We granted options under our 2004 Equity Incentive Plan, as amended (our "2004 Plan"), until July 26, 2017, when we terminated it in connection with our initial public offering. Accordingly, no shares are available for future issuance under our 2004 Plan. Our 2004 Plan continues to govern outstanding equity awards granted thereunder. The term of each stock option under the plan is no more than 10 years, and each stock option generally vests over a four-year period. 2017 Equity Incentive Plan — Our 2017 Equity Incentive Plan (our "2017 EIP") became effective on July 26, 2017, and provides for the issuance of incentive and nonqualified common stock options and restricted stock units to employees, directors, and consultants. The number of shares of common stock initially reserved for issuance under our 2017 EIP was 7,898,159. The number of shares reserved for issuance under our 2017 EIP will increase automatically on January 1 of each calendar year beginning on January 1, 2018, and continuing through January 1, 2028, by the number of shares equal to the lesser of 5% of the total outstanding shares of our common stock as of the immediately preceding December 31 or an amount determined by our board of directors. The term of each stock option and restricted stock unit under the plan will not exceed 10 years, and each award generally vests over a two-year or four-year period. We have reserved shares of common stock for future issuance under our 2017 EIP as follows: June 30, 2020 December 31, 2019 Stock options issued and outstanding 6,493,269 7,792,181 Restricted stock units issued and outstanding or deferred 4,356,392 5,023,412 Shares available for future equity grants 11,994,905 7,100,499 Total shares reserved for future issuance 22,844,566 19,916,092 2017 Employee Stock Purchase Plan — Our 2017 Employee Stock Purchase Plan (our "ESPP") was approved by our board of directors on July 27, 2017 and enables eligible employees to purchase shares of our common stock at a discount. Purchases will be accomplished through participation in discrete offering periods. We initially reserved 1,600,000 shares of common stock for issuance under our ESPP. The number of shares reserved for issuance under our ESPP will increase automatically on January 1 of each calendar year beginning after the first offering date and continuing through January 1, 2028, by the number of shares equal to the lesser of 1% of the total outstanding shares of our common stock as of the immediately preceding December 31 or an amount determined by our board of directors. On each purchase date, eligible employees will purchase our common stock at a price per share equal to 85% of the lesser of (i) the fair market value of our common stock on the first trading day of the offering period and (ii) the fair market value of our common stock on the purchase date. We have reserved shares of common stock for future issuance under our ESPP as follows: Six Months Ended June 30, 2020 Year Ended December 31, 2019 Shares available for issuance at beginning of period 3,330,271 2,890,973 Shares issued during the period 186,925 490,717 Total shares available for future issuance at end of period 3,143,346 2,400,256 Stock Options —The following table summarizes activity for stock options for the six months ended June 30, 2020 : Number of Options Weighted- Average Exercise Price Weighted-Average Remaining Contractual Life (Years) Aggregate Intrinsic Value Outstanding as of January 1, 2020 7,792,181 $ 7.00 5.28 $ 111,122 Options exercised (1,257,830) 5.97 Options forfeited (31,103) 8.93 Options expired (9,979) 8.95 Outstanding at June 30, 2020 6,493,269 7.19 4.90 225,447 Options exercisable at June 30, 2020 6,095,505 6.58 4.72 215,368 The grant date fair value of options to purchase common stock is recorded as stock-based compensation over the vesting period. As of June 30, 2020, there was $1,528 of total unrecognized compensation cost related to stock options. These costs are expected to be recognized over a weighted-average period of 0.93 years. The total fair value of stock options vested for the three months ended June 30, 2020 and 2019 was $643 and $1,297, respectively, and $1,382 and $2,746 for the six months ended June 30, 2020 and 2019, respectively. The total intrinsic value of stock options exercised for the three months ended June 30, 2020 and 2019 was $11,224 and $5,402, respectively, and $26,475 and $14,084 for the six months ended June 30, 2020 and 2019, respectively. On June 1, 2019, we granted stock options subject to performance conditions, with a target of 150,000 shares and a maximum 300,000 shares, to our chief executive officer. The options have an exercise price of $27.50 per share and have the same performance and vesting conditions as the restricted stock units subject to performance conditions that we granted in 2019 (the "2019 PSUs"). None of the options vested in the six months ended June 30, 2020. Restricted Stock Units —The following table summarizes activity for restricted stock units for the six months ended June 30, 2020 : Restricted Stock Units Weighted Average Grant-Date Fair Value Outstanding as of January 1, 2020 5,023,412 $ 18.69 Granted 551,441 29.14 Vested (1) (664,515) 18.77 Forfeited or canceled (553,946) 18.84 Outstanding or deferred as of June 30, 2020 (1) 4,356,392 $ 19.98 (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, 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. The grant date fair value of restricted stock units is recorded as stock-based compensation over the vesting period. As of June 30, 2020, there was $75,941 of total unrecognized compensation cost related to restricted stock units, which is expected to be recognized over a weighted-average period of 2.68 years. As of June 30, 2020 , there were outstanding 314,999 restricted stock units subject to performance conditions (the "PSUs") at 100% of the target level. Depending on our achievement of the performance conditions, the actual number of shares of common stock issuable upon vesting of PSUs will range from 0% to 200% of the target amount. For each PSU recipient, the award will vest, subject to the recipient continuing to provide service to us, upon our board of directors, or its compensation committee, certifying that we have achieved the PSU's related performance conditions. Stock-based compensation expense for PSUs will be recognized when it is probable that the performance conditions will be achieved. During the six months ended June 30, 2020 , we recognized a net $(254) for share-based compensation expense for PSUs, which included (i) an adjustment of $(590) for the reversal of expense from the the year ended December 31, 2019 related to expense for the PSUs we granted in 2019, as the probability of achieving the performance conditions was determined to be lower, and (ii) a charge of $336 for the six months ended June 30, 2020 . During the six months ended June 30, 2019, we recognized a net $(494) for share-based compensation expense for PSUs, which included (i) an adjustment of $(610) for the reversal of expense from the year ended December 31, 2018 related to the expense for PSUs we granted during 2018, as the probability of achieving the performance conditions was determined to not be probable, and (ii) an expense of $116 for PSUs granted in June 2019. Compensation Cost —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) changes to the probability of achieving outstanding performance-based equity awards, each as included in our consolidated statements of operations: Three Months Ended June 30, Six Months Ended June 30, 2020 2019 2020 2019 Cost of revenue $ 1,769 $ 1,328 $ 3,407 $ 2,793 Technology and development 3,124 2,685 6,772 5,341 Marketing 352 349 727 635 General and administrative 1,960 1,514 3,510 3,513 Total stock-based compensation $ 7,205 $ 5,876 $ 14,416 $ 12,282 We capitalize stock-based compensation related to work performed on internally developed software. There was $647 and $291 of stock-based compensation that was capitalized in the three months ended June 30, 2020 and 2019, respectively, and $1,151 and $561 in the six months ended June 30, 2020 and 2019, respectively. All capitalized stock-based compensation is related to employees in technology and development. |