Common Stock and Stockholders' Equity (Deficit) | Common Stock and Stockholders’ Equity (Deficit) Redeemable Convertible Preferred Stock Immediately prior to the completion of the IPO in April 2019, all shares of redeemable convertible preferred stock then outstanding were converted into 41,273,345 shares of common stock on a one -to-one basis and then immediately reclassified into common stock. Equity Incentive Plans The Company has two equity incentive plans: the 2010 Stock Plan (the 2010 Plan) and the 2019 Equity Incentive Plan (the 2019 Plan, collectively the Stock Plans). Upon completion of the Company’s IPO in April 2019, the Company ceased granting awards under the 2010 Plan, and all shares that remained available for future issuance under the 2010 Plan at that time were transferred to the 2019 Plan. The 2019 Plan superseded and replaced the 2010 Plan. Under the 2019 Plan, the Company’s Board of Directors (the Board) and any other committee or subcommittee of the Board may grant stock options and restricted stock awards (RSAs) and restricted stock units (RSUs) to employees, consultants, and advisors of the Company. Through October 31, 2019 , the Company has granted stock options, RSAs, and RSUs. As of October 31, 2019 and January 31, 2019 , respectively, the Company was authorized to grant up to 13,049,689 shares and 23,929,932 shares of common stock under the Stock Plans. The Company has issued stock options and RSAs to employees and non-employee directors under the 2010 Plan, and certain of these awards allow for early exercise. The Company has issued stock options and RSUs to employees pursuant to the 2019 Plan. Stock options are granted with exercise prices at the fair value of the underlying common stock on the grant date, in general vest based on continuous employment over four years and expire 10 years from the date of grant. RSUs are measured based on the grant date fair value of the awards and in general vest based on continuous employment over four years . In March 2019, the Company granted 3,041,000 stock options to existing employees with 50 percent of these options vesting over four years from the grant date and 50 percent vesting over five years from the grant date. The Company currently uses authorized and unissued shares to satisfy stock award exercises. As of October 31, 2019 and January 31, 2019 , there were 12,249,794 shares and 2,221,216 shares available for future issuance under the Stock Plans, respectively. Shares of common stock reserved for future issuance are as follows: October 31, 2019 Stock options and unvested RSUs outstanding 15,643,007 Available for future stock option and RSU grants 12,249,794 Available for ESPP 1,850,000 Total common stock reserved at October 31, 2019 29,742,801 Stock Option Activity Stock option activity is as follows: Number of Shares Weighted Average Exercise Price Weighted Average Remaining Contractual Term Aggregate Intrinsic Value (in thousands) Outstanding at January 31, 2019 14,006,222 $ 4.32 8.0 years $ 142,840 Granted 3,773,315 $ 15.87 Exercised (2,091,575 ) $ 2.67 Canceled (755,794 ) $ 8.34 Outstanding at October 31, 2019 14,932,168 $ 7.28 8.0 years $ 234,653 Vested as of October 31, 2019 6,563,556 $ 3.41 7.2 years $ 128,502 Stock options granted during the three months ended October 31, 2019 and 2018 had a weighted average grant date fair value of $11.72 and $5.50 per share, respectively. The aggregate intrinsic value of stock options exercised during the three months ended October 31, 2019 and 2018 was $21.8 million and $4.0 million , respectively. Stock options granted during the nine months ended October 31, 2019 and 2018 had a weighted average grant date fair value of $10.84 and $4.60 per share, respectively. The aggregate intrinsic value of stock options exercised during the nine months ended October 31, 2019 and 2018 was $52.5 million and $8.6 million , respectively. The intrinsic value for options exercised is the difference between the market value of the stock and the exercise price of the stock option at the date of exercise. As of October 31, 2019 and January 31, 2019 , respectively, there was approximately $52.5 million and $30.6 million of total unrecognized compensation cost related to unvested stock options granted under the Stock Plans, which will be recognized over a weighted average period of 3.4 years and 2.7 years , respectively. Restricted Stock Units A summary of the Company’s RSU activity and related information is as follow: Number of RSUs Weighted Average Grant Date Fair Value Per Share Outstanding at January 31, 2019 — $ — Granted 711,509 $ 30.69 Vested, net of shares withheld for employee payroll taxes (1,080 ) $ 32.51 Canceled (2,108 ) $ 46.26 Outstanding at October 31, 2019 708,321 $ 30.64 As of October 31, 2019 , there was $20.9 million of unrecognized stock-based compensation expense related to unvested RSUs, which is expected to be recognized over a weighted average period of 3.8 years based on vesting under the award service conditions. Employee Stock Purchase Plan In April 2019, the Board adopted and approved the 2019 Employee Stock Purchase Plan (ESPP), which became effective on April 11, 2019. The ESPP initially reserved and authorized the issuance of up to a total of 1,850,000 shares of common stock to participating employees. The initial offering period began April 11, 2019 and will end on June 15, 2021, with purchase dates of December 13, 2019, June 15, 2020, December 15, 2020 and June 15, 2021. The ESPP generally provides for 24 -month offering periods beginning June 15 and December 15 of each year, with each offering period consisting of four six -month purchase periods, except for the initial offering period which began on April 11, 2019 and will end on December 15, 2019. On each purchase date, eligible employees will purchase the shares at a price per share equal to 85% of the lesser of (1) the fair market value of the Company’s stock as of the beginning of the offering period or (2) the fair market value of the Company’s stock on the purchase date, as defined in the ESPP. The Company recognized $1.5 million and $3.7 million of stock-based compensation expense related to ESPP during the three and nine months ended October 31, 2019 , respectively beginning upon the IPO in April 2019. As of October 31, 2019 , $4.1 million has been withheld on behalf of employees for a future purchase under the ESPP. There were no purchases for the three and nine months ended October 31, 2019 related to the ESPP. Warrant Issued as Charitable Contribution In fiscal 2019, the Company commenced an initiative to donate product, equity, and employee time for charitable purposes. In June 2018, as part of this initiative, the Company issued to the Tides Foundation a warrant to purchase up to 648,092 shares of the Company’s common stock, exercisable at a price of $0.01 per share. The common stock warrant was automatically net exercised for 647,822 shares of common stock upon the closing of the IPO. The Company recognized $6.2 million of non-cash charitable contribution expense during the nine months ended October 31, 2018 and this amount is included in general and administrative expense in the accompanying condensed consolidated statement of operations. Common Stock Transfer During the three and nine months ended October 31, 2018, certain of the Company’s investors acquired outstanding common stock from current or former employees at a purchase price greater than or equal to the estimated fair value at the time of the transactions. For the shares acquired at a price in excess of fair value during the three and nine months ended October 31, 2018, the Company recorded stock-based compensation expense for the difference between the price paid and the estimated fair value on the date of the transactions of $5.5 million . The Company recorded $3.8 million of this expense in research and development expense, $1.4 million in general and administrative expense and $0.3 million in sales and marketing expense. In connection with these stock transfers, the Company either waived or assigned its rights of first refusal or other transfer restrictions applicable to such shares. There were no such transactions during the three or nine months ended October 31, 2019. Stock-Based Compensation The Company uses the Black-Scholes option-pricing model to estimate the fair value of stock options on the date of grant. The Company uses the fair value of RSUs based on the fair value of the underlying shares on the date of grant. The Company accounts for forfeitures as they occur. Stock-based compensation expense included in the Company’s condensed consolidated statements of operations is as follows (in thousands): Three Months Ended October 31, Nine Months Ended October 31, 2019 2018 2019 2018 Cost of revenue $ 303 $ 71 $ 773 $ 202 Research and development 1,462 6,567 3,760 7,680 Sales and marketing 2,295 1,198 6,084 2,964 General and administrative (1) 3,287 2,340 8,775 5,016 Total $ 7,347 $ 10,176 $ 19,392 $ 15,862 (1) Stock-based compensation expense above does not include $6.2 million of non-cash charitable contribution expense. |