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Equity Incentive Plans | 3 Months Ended
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Apr. 30, 2024
Share-Based Payment Arrangement [Abstract] |
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 three months ended April 30, 2024, the number of shares available for grant under the 2018 Plan was increased by 1,845,970 shares. As of April 30, 2024, there were 4,613,392 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):
| Three Months Ended April 30,
| 2023 |  | 2024
Cost of revenue: |  |  |
Subscription | $ | 618 |  | $ | 798
Professional services and other | 479 |  | 333
Sales and marketing | 6,730 |  | 5,314
Research and development | 4,975 |  | 4,422
General and administrative | 3,508 |  | 3,084
Interest expense | 162 |  |  | 191 |
Total | $ | 16,472 |  |  | $ | 14,142 |
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 no stock options granted during the three months ended April 30, 2023 and April 30, 2024. The following table sets forth the outstanding common stock options and related activity for the three months ended April 30, 2024:
| Shares Subject to Outstanding Options |  | Weighted- Average Exercise Price per Share |  | Weighted-Average Remaining Contractual Term (years) |  | Aggregate Intrinsic Value (in thousands)
Outstanding as of January 31, 2024 | 793,314 |  | $ | 26.52 |  |  | 1.0 |  | $ | — |
Expired | (28,867) |  |  | 26.44 |  |  |  |
Outstanding as of April 30, 2024 | 764,447 |  | $ | 26.52 |  |  | 0.6 |  | $ | — |
The aggregate intrinsic value of options exercised was $0 million during the three months ended April 30, 2023, and there were no options exercised during the three months ended April 30, 2024. The intrinsic value represents the excess of the 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 April 30, 2024 is based on the market closing price of the Company's Class B common stock on that date. As of April 30, 2024, all outstanding stock options were vested and exercisable and stock-based compensation expense related to all outstanding stock options has been recognized. Restricted Stock Units Restricted stock units (RSUs) granted under the Plan primarily vest and settle upon the satisfaction of a service-based condition. The service-based condition for these awards is generally satisfied over three or four years with a cliff vesting period of one or two years and quarterly vesting thereafter. RSUs include performance-based restricted stock units (PSUs), which are subject to a market condition and settle upon the satisfaction of a service-based condition. Disclosures related to RSU activity include the impact of PSUs. The following table sets forth the outstanding RSUs and related activity for the three months ended April 30, 2024:
| Number of Shares |  | Weighted- Average Grant Date Fair Value
Outstanding as of January 31, 2024 | 4,726,290 |  | $ | 25.61 |
Granted | 441,694 |  | 10.54 |
Vested | (1,111,795) |  |  | 22.32 |
Canceled | (64,061) |  |  | 49.03 |
Outstanding as of April 30, 2024 | 3,992,128 |  | $ | 25.25 |
As of April 30, 2024, there was $87.1 million of unrecognized stock-based compensation expense related to outstanding RSUs which is expected to be recognized over a weighted-average period of 2.1 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. During the three months ended April 30, 2024, the number of shares available under the ESPP was increased by 553,791 shares. As of April 30, 2024, there were 601,136 shares available under the ESPP. The ESPP generally 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 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 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 April 30, 2024, a total of approximately 328,820 shares were issuable to employees based on estimated shares available and contribution elections made under the ESPP. Estimated shares available were estimated assuming that the plan will be increased by an amount approximating 1.5% of shares outstanding as of January 31, 2025. As of April 30, 2024, total unrecognized stock-based compensation related to the ESPP was $0.9 million, which is expected to be recognized over a weighted-average period of 0.8 years.

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