Equity and Equity Compensation Plans | Equity and Equity Compensation Plans Common Stock —As of March 31, 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 March 31, 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 , of which no shares were issued or outstanding. Amended and Restated 2004 Equity Incentive Plan — We granted options under our 2004 Equity Incentive Plan, as amended ("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 ("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, officers, 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 the 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 four -year period We have reserved shares of common stock for future issuance under our 2017 EIP as follows: March 31, 2020 December 31, 2019 Stock options issued and outstanding 7,028,719 7,792,181 Restricted stock units issued and outstanding 4,681,875 5,023,412 Shares available for future equity grants 11,899,400 7,100,499 Total shares reserved for future issuance 23,609,994 19,916,092 2017 Employee Stock Purchase Plan — Our 2017 Employee Stock Purchase Plan ("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: Three Months Ended March 31, 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 — 490,717 Total shares available for future issuance at end of period 3,330,271 2,400,256 Stock Options —The following table summarizes activity for stock options for the three months ended March 31, 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 (738,398) 5.30 Options forfeited (20,798) 9.01 Options canceled (4,266) 10.80 Outstanding as of March 31, 2020 7,028,719 $ 7.17 5.12 $ 59,786 Options exercisable as of March 31, 2020 6,472,555 $ 6.54 4.93 $ 57,443 The grant date fair value of options to purchase common stock is recorded as stock-based compensation over the vesting period. As of March 31, 2020 , there was $2,255 of total unrecognized compensation cost related to stock options. These costs are expected to be recognized over a weighted-average period of 1.01 years . The total fair value of stock options vested during the three months ended March 31, 2020 and 2019 was $739 and $1,449 , respectively. The total intrinsic value of stock options exercised during the three months ended March 31, 2020 and 2019 was $15,251 and $8,682 , 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 three months ended March 31, 2020 . Restricted Stock Units —The following table summarizes activity for restricted stock units for the three months ended March 31, 2020 : Restricted Stock Units Weighted Average Grant-Date Fair Value Outstanding as of January 1, 2020 5,023,412 $ 18.69 Granted 141,413 27.06 Vested (320,440 ) 19.36 Forfeited or canceled (162,510 ) 19.29 Outstanding as of March 31, 2020 4,681,875 $ 18.87 The grant date fair value of restricted stock units is recorded as stock-based compensation over the vesting period. As of March 31, 2020 , there was $77,435 of total unrecognized compensation cost related to restricted stock units, which is expected to be recognized over a weighted-average period of 2.86 years years. As of March 31, 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 three months ended March 31, 2020 , we recognized $(464) , which includes (i) an adjustment of $(617) for the reversal of expense from the year ended December 31, 2019 related to the 2019 PSUs as the probability of achieving the performance conditions was adjusted downward and (ii) a charge of $153 related to the 2019 PSUs expense for the three months ended March 31, 2020 . For the three months ended March 31, 2019, we recognized $278 for share-based compensation expense related to the PSUs we granted during 2018, which was later reversed as the probability of achieving the performance conditions was determined to be not probable. 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 March 31, 2020 2019 Cost of revenue $ 1,638 $ 1,465 Technology and development 3,648 2,656 Marketing 375 286 General and administrative 1,550 1,999 Total stock-based compensation $ 7,211 $ 6,406 We capitalize stock-based compensation related to work performed on internally developed software. There was $504 and $270 of stock-based compensation that was capitalized in the three months ended March 31, 2020 and 2019 , respectively. All capitalized stock-based compensation is related to employees in technology and development. |