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 nine months ended October 31, 2022, the number of shares available for grant under the 2018 Plan was increased by 1,649,674 shares. As of October 31, 2022, there were 4,033,022 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 October 31,				Nine Months Ended October 31,
	2021		2022		2021		2022
Cost of revenue:
Subscription	$	800	$	667	$	1,768	$	2,176
Professional services and other	563		308		1,168		1,339
Sales and marketing	6,718		7,336		15,192		23,284
Research and development	5,363		5,909		10,603		19,196
General and administrative	4,543		4,807		11,596		18,319
Interest expense	176		180		524		550
Total	$	18,163	$	19,207	$	40,851	$	64,864

Stock options typically vest over a four-year period and have a term of ten years from the date of grant. No stock options were granted during the three and nine months ended October 31, 2021 and the three and nine months ended October 31, 2022.

The following table sets forth the outstanding common stock options and related activity for the nine months ended October 31, 2022:


	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, 2022	963,288	$	26.16	2.9	$	20,166

Exercised	(47,389)	18.17

Expired	(8,990)	37.61
Outstanding as of October 31, 2022	906,909	$	26.47	2.1	$	77
Vested and exercisable at October 31, 2022	904,304	$	26.45	2.1	$	77

The aggregate intrinsic value of options exercised was $7.4 million and $0.1 million for the three months ended October 31, 2021 and 2022, respectively, and $14.5 million and $1.5 million for the nine months ended October 31, 2021 and 2022, respectively. 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 October 31, 2022 is based on the market closing price of the Company's Class B common stock on that date.

As of October 31, 2022, there was $34,000 of unrecognized stock-based compensation expense related to outstanding stock options which is expected to be recognized over a weighted-average period of 0.2 years.

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.

During the three months ended April 30, 2022 the Company granted 71,667 PSUs with both a market and service-based condition. The PSUs are eligible to vest in three equal tranches on the one, two, and three year anniversaries of the grant date upon Company's Class B common stock achieving a 30-day volume-weighted average price for 30 consecutive trailing

trading days of $60.00 per share, $70.00 per share, and $90.00 per share, respectively. The grant date fair values of the PSUs granted were $36.07 per share, $33.98 per share, and $30.26 per share, respectively, as determined by a Monte Carlo simulation model.

The following table sets forth the outstanding RSUs and related activity for the nine months ended October 31, 2022:


	Number of Shares	Weighted- Average Grant Date Fair Value
Outstanding as of January 31, 2022	4,338,619	$	55.40
Granted	2,005,478	43.25
Vested	(1,339,137)	51.82
Canceled	(1,008,921)	53.35
Outstanding as of October 31, 2022	3,996,039	$	51.01

As of October 31, 2022, there was $179.0 million of unrecognized stock-based compensation expense related to outstanding RSUs which is expected to be recognized over a weighted-average period of 2.7 years.

In March 2022, the Company paid out certain fiscal 2022 bonuses in the form of vested RSUs instead of cash, resulting in the issuance of approximately 90,000 shares of the Company's Class B common stock. The Company recognized $3.6 million of stock-based compensation related to these bonuses during the three months ended April 30, 2022.

In April 2022, the Company modified and accelerated the vesting of awards for certain employees, resulting in the issuance of approximately 56,000 shares of the Company's Class B common stock. The Company recognized $2.6 million of stock-based compensation related to these modifications during the three months ended April 30, 2022.

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 nine months ended October 31, 2022, the number of shares available under the ESPP was increased by 164,967 shares. As of October 31, 2022, there were 307 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 October 31, 2022, a total of approximately 368,369 shares were issuable to employees based on estimated shares available and contribution elections made under the ESPP. Shares available were estimated assuming that the plan will be