Each share of common stock has the right to one vote. The holders of the common stock are also entitled to receive dividends whenever funds are legally available and when declared by the board of directors of the Company (the “Board of Directors”), subject to the prior rights of holders of all classes of stock outstanding having priority rights as to dividends. No dividends have been declared or paid since inception.

The 2016 Equity Incentive Plan (the “2016 Plan”) was approved by the Company’s stockholders in September 2016. The 2016 Plan provides for the grant of incentive stock options, nonstatutory stock options, restricted stock, restricted stock units, stock appreciation rights and performance cash awards. Awards could be granted under the 2016 Plan beginning on the effective date of the registration statement relating to the Company’s initial public offering, October 5, 2016. The 2016 Plan replaced the Company’s 2006 Stock Plan; however, awards outstanding under the 2006 Stock Plan will continue to be governed by their existing terms.

As of January 31, 2022, the Company had 12,682,224 shares of its common stock available for future issuance under the 2016 Plan. The number of shares reserved for issuance under the 2016 Plan will automatically increase on the first day of each fiscal year during the term of the 2016 Plan by a number of shares equal to 5% of its outstanding shares of common stock on the last day of the prior fiscal year. The number and class of shares reserved under the Company’s 2016 Plan will be adjusted in the event of a stock split, stock dividend or other changes in its capitalization.


	Options Outstanding
	Outstanding Stock Options	Weighted- Average Exercise Price		Weighted-Average Remaining Contractual Life (in years)	Aggregate Intrinsic Value
Balance, January 31, 2021	2,608,640	$	20.65	5.6	$	754,478

Options exercised	(759,390)	$	12.42	—	—
Options forfeited	(8,303)	$	70.45	—	—
Balance, January 31, 2022	1,840,947	$	23.82	4.7	$	203,339
Exercisable at January 31, 2022	1,784,435	$	22.13	4.7	$	200,107

The aggregate intrinsic value of options vested and exercisable as of January 31, 2022 is calculated based on the difference between the exercise price and the fair value of the Company’s common stock as of January 31, 2022. The aggregate intrinsic value of exercised options was $172.1 million, $375.7 million and $318.2 million for the years ended January 31, 2022, 2021 and 2020, respectively, and is calculated based on the difference between the exercise price and the fair value of the Company’s common stock as of the exercise date.

No options were granted during the years ended January 31, 2022 and 2021. The weighted-average grant date fair value of options granted for the year ended January 31, 2020 was $41.81 per share. The total grant date fair value of options vested during fiscal 2022, 2021 and 2020 was $3.9 million, $8.0 million and $8.6 million, respectively.


	Number of RSUs Outstanding	Weighted- Average Grant Date Fair Value
Awarded and unvested at January 31, 2021	2,530,280	$	123.56
Awards granted	1,153,149	$	238.07
Awards vested	(1,235,810)	$	109.21
Awards forfeited	(322,970)	$	186.22
Awarded and unvested at January 31, 2022	2,124,649	$	184.56

The Board of Directors adopted the 2016 Employee Stock Purchase Plan (the “ESPP”) in September 2016 and it has been approved by the Company’s stockholders. The ESPP allows eligible employees to purchase shares of common stock through payroll deductions and is intended to qualify under Section 423 of the Internal Revenue Code.

As of January 31, 2022, the Company had 2,326,540 shares of its common stock available for future issuances under the ESPP. The number of shares reserved for issuance under the ESPP will automatically increase on the first day of each fiscal year during the term of the ESPP by a number of shares equal to the least of (i) 1% of its outstanding shares of common stock on the last day of the prior fiscal year, (ii) 1,250,000 shares or (iii) a lesser number of shares determined by the board of directors. The number and class of shares reserved under the ESPP will be adjusted in the event of a stock split, stock dividend or other changes in its capitalization.

Each offering period will last a number of months determined by the administrator, up to a maximum of 27 months. The initial offering period began on the effective date of the Company’s initial public offering, October 5, 2016, and ended on September 15, 2018, and new 24 month offering periods will begin on each March 16 and September 16 thereafter. Currently, each offering period consists of four consecutive purchase periods, of approximately six months duration, at the end of which payroll contributions are used to purchase shares of the Company’s common stock. Participants may purchase the Company’s common stock through payroll deductions, up to a maximum of 15% of their eligible compensation. Participants may withdraw from the ESPP and receive a refund of their accumulated payroll contributions at any time prior to a purchase date. Unless changed by the administrator, the purchase price for each share of common stock purchased under the ESPP will be 85% of the lower of the fair market value per share on the first day of the applicable offering period or the fair market value per share on the applicable purchase date.

The Company purchased 156,810 and 209,306 shares of common stock under the 2016 ESPP during the years ended January 31, 2022 and 2021, respectively. The Company selected the Black-Scholes option-pricing model as the method for determining the estimated fair value for the Company’s 2016 ESPP. As of January 31, 2022, total unrecognized compensation cost related to the 2016 ESPP was $15.3 million which will be amortized over a weighted-average period of approximately 1.6 years.

In September 2016, the Board of Directors of the Company granted 544,127 stock options to the Chief Executive Officer (the “2016 CEO Grant”) under the 2006 Stock Plan with an exercise price of $13.04 per share. The 2016 CEO Grant is eligible to vest based on the achievement of market capital appreciation targets after the consummation of the initial public offering, as well as continuous service over a four-year period following the grant date. In March 2018, the Board of Directors granted 334,742 stock options to the Chief Executive Officer (the “2018 CEO Grant”) under the 2016 Equity Plan with an exercise price of $48.47 per share. The 2018 CEO Grant is eligible to vest based on the achievement of a stock price appreciation target as well as continuous service over a four-year period following the grant date. The fair values of the 2016 and 2018 CEO Grants were determined using a Monte Carlo simulation approach. The Company amortizes the fair value of the option awards using the graded-vesting method.

In March 2020, the Board of Directors of the Company granted market-based restricted stock unit awards (the “2020 PSU Grant”) to certain members of management. The target number of market-based restricted stock unit awards granted was 100,178. The number of shares that could be earned will range from 0% to 200% of the target number of shares, based on the relative growth of the per share price of the Company’s common stock as compared to the Nasdaq Composite Index over the three-year performance period ending on the third anniversary of the date of grant and subject to continuous employment through such date. The fair value of the 2020 PSU Grant was determined using a Monte Carlo simulation approach. The Company amortizes the fair value of the 2020 PSU Grant using the straight-line method over the three-year performance term.

In March 2021, the Board of Directors of the Company granted market-based restricted stock unit awards (the “2021 PSU Grant”) to certain members of management. The target number of market-based restricted stock unit awards granted was 109,249. The number of shares that could be earned will range from 0% to 200% of the target number of shares, based on the relative growth of the per share price of the Company’s common stock as compared to the Nasdaq Composite Index over the three-year performance period ending on the third anniversary of the date of grant and subject to continuous employment through such date. Additionally, if necessary, the payout percentage will be decreased so that the overall value delivered to the award holder (total payout number of shares multiplied by the stock price on the vesting date) will be capped at four times the target value (target number of shares multiplied by the stock price on the date of grant). The fair value of the 2021 PSU Grant was determined using a Monte Carlo simulation approach. The Company amortizes the fair value of the 2021 PSU Grant using the straight-line method over the three-year performance term.

As of January 31, 2022, all market-based milestones of the 2016 CEO Grant and 2018 CEO Grant were achieved, resulting in 544,127 shares and 320,794 shares, respectively, being vested and exercisable. As of January 31, 2022, the three-year performance period related to the 2020 PSU Grant and 2021 PSU Grant had not been completed, both resulting in no shares being vested or exercisable. Stock-based compensation expense recognized for market-based awards was approximately $13.3 million, $6.6 million and $1.7 million for the years ended January 31, 2022, 2021 and 2020, respectively.


	For the year ended January 31,
	2022		2021		2020
Cost of revenue:
Subscription	$	14,920	$	11,438	$	6,982
Professional services and other	16,991		15,563		7,773
Research and development	44,119		37,685		20,159
Sales and marketing	52,109		48,414		23,352
General and administrative	71,756		55,750		23,110
Total	$	199,895	$	168,850	$	81,376

Out of the total stock-based compensation expense for the year ended January 31, 2021, approximately $27.8 million was a one-time post acquisition stock-based compensation expense resulting from the accelerated vesting of legacy employee stock awards in conjunction with the acquisition of LLamasoft.

As of January 31, 2022, 2021 and 2020, there was approximately $1.6 million, $4.5 million and $11.5 million, respectively, of total unrecognized compensation cost related to unvested stock options granted. This unrecognized compensation cost as of January 31, 2021, is expected to be recognized over an estimated weighted-average amortization period of approximately 1.1 years.

As of January 31, 2022, 2021 and 2020, there was approximately $352.0 million, $319.6 million and $186.3 million, respectively, of total unrecognized compensation cost related to unvested restricted stock units granted to employees. This unrecognized compensation cost as of January 31, 2022 is expected to be recognized over an estimated weighted-average amortization period of approximately 2.7 years.


	For the year ended January 31,
	2022				2021				2020
Employee Stock Options:
Expected term (in years)	—				—				6.0
Volatility	—				—				42.7%
Risk-free interest rate	—				—				2.4%
Dividend yield	—				—				—
Employee Stock Purchase Plan:
Expected term (in years)	0.5		-	2.0	0.5		-	2.0	0.5		-	2.0
Volatility	42.1	%	-	61.2 %	48.6	%	-	60.7 %	44.4	%	-	65.9 %
Risk-free interest rate	0.0%		-	0.2 %	0.1	%	-	0.4 %	1.7	%	-	2.5 %
Dividend yield	—				—				—
Market-Based Awards:
Expected term (in years)	3.0				3.0				—
Volatility	54.6%				48.4%				—
Risk-free interest rate	0.3%				0.4%				—
Dividend yield	—				—				—

•Expected Term. The expected term for the employee stock purchase plan ranges from six months, the length of one purchase period, to two years, the length of one offering period. The market-based awards have a three-year expected term.

•Expected Volatility. The Company uses its historical trading prices to calculate the expected volatility in determining the fair value of the shares granted under the ESPP and market-based awards. In addition, beginning from the first quarter of fiscal year 2020, the Company began using its own historical volatility in combination with publicly traded peers’ volatility to determine the expected volatility of stock options.