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, 2024, the number of shares available for grant under the 2018 Plan was increased by 1,741,824 shares. As of January 31, 2024, there were 3,116,044 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,
	2022		2023		2024
Cost of revenue:
Subscription	$	2,819	$	2,676	$	2,810
Professional services and other	1,753		1,822		1,735
Sales and marketing	21,241		30,636		25,015
Research and development	15,853		24,335		19,520
General and administrative	18,155		23,680		14,565
Interest expense	705		710		703
Total	$	60,526	$	83,859	$	64,348

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 years ended January 31, 2022, 2023, and 2024.

The following table sets forth the outstanding common stock options and related activity for the years ended January 31, 2022, 2023 and 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, 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
Exercised	(47,389)	18.17

Expired	(39,615)	30.48
Outstanding as of January 31, 2023	876,284	26.40		1.9	59
Exercised	(7,638)	8.40

Expired	(75,332)	26.95
Outstanding as of January 31, 2024	793,314	$	26.52	1.0	$	—
Vested and exercisable at January 31, 2024	793,314	$	26.52	1.0	$	—

The aggregate intrinsic value of options exercised was $17.3 million, $1.5 million and $0.0 million for the years ended January 31, 2022, 2023 and 2024, 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 January 31, 2024 is based on the market closing price of the Company's Class B common stock on that date.

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. These awards were subsequently modified and related to the service-based condition, which resulted in a $1.1 million reversal of stock-based compensation expense during the year ended January 31, 2024. Additionally, 23,889 of these PSUs were canceled during the year ended January 31, 2024.

The following table sets forth the outstanding RSUs and related activity for the years ended January 31, 2022, 2023 and 2024:


	Number of Shares	Weighted- Average Grant Date Fair Value
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
Granted	2,314,571	39.46
Vested	(1,630,656)	51.26
Canceled	(1,128,440)	53.27
Outstanding as of January 31, 2023	3,894,094	48.27
Granted	3,523,844	14.38
Vested	(1,742,989)	46.69
Canceled	(948,659)	38.85
Outstanding as of January 31, 2024	4,726,290	$	25.61

As of January 31, 2024, there was $99.8 million of unrecognized stock-based compensation expense related to outstanding RSUs which is expected to be recognized over a weighted-average period of 2.2 years.

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 year ended January 31, 2024, the number of shares available under the ESPP was increased by 522,547 shares. As of January 31, 2024, there were 190,551 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 January 31, 2024, a total of approximately 494,569 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, 2023. As of January 31, 2024,

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,
	2022	2023	2024
Expected stock price volatility	41% - 82%	60% - 90%	74% - 93%
Expected term	0.5 - 1.0 year	0.5 - 1.0 year	0.5 - 1.0 year
Risk-free interest rate	0.04% - 0.09%	1.09% - 4.05%	4.60% - 5.58%
Expected dividend yield	–	–	–