Equity Incentive Plans | Equity Incentive Plans In April 2011, the Company established the 2011 Equity Incentive Plan (2011 Plan), which was amended in September 2011 to provide for the issuance of stock options and other stock-based awards. In June 2018, the Company adopted the 2018 Equity Incentive Plan (2018 Plan). The 2018 Plan provides for the grant of incentive and nonstatutory stock options, restricted stock, RSUs, stock appreciation rights, performance units, and performance shares to employees, consultants, and members of the Company's board of directors. The number of shares available for issuance under the 2018 Plan includes an annual increase on the first day of each fiscal year equal to the least of: (1) 3,500,000 shares; (2) 5% of the outstanding shares of Class A and Class B common stock as of the last day of the immediately preceding fiscal year; and (3) such other amount as the Company's board of directors may determine no later than the last day of the immediately preceding year. During the year ended January 31, 2022, the number of shares available for grant under the 2018 Plan was increased by 1,526,754 shares. As of January 31, 2022, there were 3,370,915 shares available for grant under the 2018 Plan. In connection with the IPO, the 2011 Plan was terminated. With the establishment of the 2018 Plan, the Company no longer grants equity-based awards under the 2011 Plan and any shares that expire, terminate, are forfeited or repurchased by the Company, or are withheld by the Company to cover tax withholding obligations, under the 2011 Plan, will become available for future grant under the 2018 Plan. The Company recognized stock-based compensation expense related to its equity incentive plans as follows (in thousands): Year Ended January 31, 2020 2021 2022 Cost of revenue: Subscription $ 507 $ 1,213 $ 2,819 Professional services and other 404 843 1,753 Sales and marketing 10,770 10,936 21,241 Research and development 6,339 9,095 15,853 General and administrative 5,637 11,218 18,155 Interest expense 190 444 705 Total $ 23,847 $ 33,749 $ 60,526 Stock Options Stock options typically vest over a four-year period and have a term of ten years from the date of grant. There were 25,000 stock options granted during the year ended January 31, 2020 and no stock options granted during the years ended January 31, 2021 and 2022. The weighted-average grant-date fair value of stock options granted was $14.95 per share for the year ended January 31, 2020. The grant-date fair value of stock options was estimated using the Black-Scholes option pricing model with the following weighted-average assumptions: Year Ended January 31, 2020 2021 2022 Expected stock price volatility 47% — — Expected life of options 6 years — — Risk-free interest rate 2.47% — — Expected dividend yield — — — Fair value of common stock $31.20 — — The following table sets forth the outstanding common stock options and related activity for the years ended January 31, 2020, 2021 and 2022: Shares Weighted- Average Exercise Weighted-Average Remaining Contractual Term (years) Aggregate Intrinsic Value (in thousands) Outstanding as of January 31, 2019 1,856,339 $ 23.64 5.6 $ 8,443 Granted 25,000 31.20 Exercised (94,603) 16.99 Forfeited (11,010) 28.24 Expired (30,311) 33.64 Outstanding as of January 31, 2020 1,745,415 23.91 4.6 5,152 Exercised (374,049) 21.64 Forfeited (2,112) 27.96 Expired (72,751) 37.53 Outstanding as of January 31, 2021 1,296,503 23.79 3.7 51,339 Exercised (332,137) 16.92 Forfeited (1,009) 28.20 Expired (69) 40.02 Outstanding as of January 31, 2022 963,288 $ 26.16 2.9 $ 20,166 Vested and exercisable at January 31, 2022 955,996 $ 26.12 2.8 $ 20,051 The aggregate intrinsic value of options exercised was $1.6 million, $10.8 million and $17.3 million for the years ended January 31, 2020, 2021 and 2022, respectively. The intrinsic value represents the excess of the estimated market closing price of the Company's common stock on the date of exercise over the exercise price of each option. The intrinsic value of options as of January 31, 2022 is based on the market closing price of the Company's Class B common stock on that date. As of January 31, 2022, there was $0.1 million of unrecognized stock-based compensation expense related to outstanding stock options which is expected to be recognized over a weighted-average period of 0.6 years. Restricted Stock Units Restricted stock units (RSUs) granted under the Plan vest and settle upon the satisfaction of a service-based condition. The service-based condition for these awards is generally satisfied over three one The following table sets forth the outstanding RSUs and related activity for the years ended January 31, 2020, 2021 and 2022: Number of Shares Weighted- Average Grant Date Fair Value Outstanding as of January 31, 2019 2,328,122 $ 19.77 Granted 1,113,913 28.82 Vested (982,591) 21.76 Canceled (282,639) 20.52 Outstanding as of January 31, 2020 2,176,805 23.40 Granted 3,209,165 25.94 Vested (1,028,734) 21.71 Canceled (499,075) 23.22 Outstanding as of January 31, 2021 3,858,161 25.97 Granted 2,540,946 77.98 Vested (1,681,544) 25.37 Canceled (378,944) 40.42 Outstanding as of January 31, 2022 4,338,619 $ 55.40 As of January 31, 2022, there was $208.5 million of unrecognized stock-based compensation expense related to outstanding RSUs which is expected to be recognized over a weighted-average period of 3.1 years. Employee Stock Purchase Plan In June 2018, the Company's board of directors adopted the ESPP. The number of shares of Class B common stock available for issuance under the ESPP increases on the first day of each fiscal year equal to the least of: (1) 1,050,000 shares of Class B common stock, (2) 1.5% of the outstanding shares of Class A and Class B common stock of the Company on the last day of the immediately preceding fiscal year, and (3) such other amount as the administrator of the ESPP may determine on or before the last day of the immediately preceding year. The administrator elected to forgo an increase in the number of shares available under the ESPP and no shares were added during the year ended January 31, 2022. As of January 31, 2022, there were 299 shares available under the ESPP. The ESPP generally provides for consecutive overlapping 24-month offering periods comprising four six-month purchase periods; provided, however, that the first purchase period in the first offering period will have a duration of approximately nine months. The offering periods are scheduled to start on the first trading day on or after April 1 and October 1 of each year. The ESPP is intended to qualify as a tax-qualified plan under Section 423 of the Internal Revenue Code and permits participants to elect to purchase shares of Class B common stock through payroll deductions of up to 15% of their eligible compensation. A participant may purchase a maximum of 2,000 shares during each purchase period. In September 2020, the ESPP was amended for all offering periods beginning on or after September 18, 2020. The amended ESPP provides for consecutive overlapping 12-month offering periods comprising two six-month purchase periods. The offering periods are scheduled to start on the first trading day on or after April 1 and October 1 of each year. The amended ESPP is intended to qualify as a tax-qualified plan under Section 423 of the Internal Revenue Code and permits participants to elect to purchase shares of Class B common stock through payroll deductions of up to 25% of their eligible compensation. Under the amended ESPP, a participant may purchase a maximum of 300 shares during each purchase period. Amounts deducted and accumulated by the participant will be used to purchase shares of Class B common stock at the end of each purchase period. The purchase price of the shares will be 85% of the lower of the fair market value of Class B common stock on the first trading day of each offering period or the fair market value of Class B common stock on the applicable exercise date. If the fair market value of a share of Class B common stock on the exercise date of an offering period is less than it was on the first trading day of that offering period, participants automatically will be withdrawn from that offering period following their purchase of shares on the exercise date and will be re-enrolled in a new offering period. Participants may end their participation at any time during an offering period and will be paid their accrued contributions that have not yet been used to purchase shares of Class B common stock. Participation ends automatically upon termination of employment. As of January 31, 2022, a total of approximately 165,266 shares were issuable to employees based on anticipated shares available and contribution elections made under the ESPP. As of January 31, 2022, total unrecognized stock-based compensation related to the ESPP was $1.6 million, which is expected to be recognized over a weighted-average period of 0.2 years. The fair value of the purchase rights for the ESPP are estimated on the date of grant using the Black-Scholes option-pricing model with the following assumptions: Year Ended January 31, 2020 2021 2022 Expected stock price volatility 43% - 52% 49% - 83% 41% - 82% Expected term 0.5 - 2.0 years 0.5 - 2.0 years 0.5 - 1.0 year Risk-free interest rate 1.56% - 2.46% 0.11% - 0.23% .04% - .09% Expected dividend yield – – – |