Stock-Based Compensation

3 Months Ended

Apr. 30, 2020

Share-based Payment Arrangement [Abstract]

We maintain two stock-based compensation plans: the 2017 Equity Incentive Plan (2017 Plan) and the 2008 Equity Incentive Plan (2008 Plan), collectively referred to as the Stock Plans. We do not expect to grant any additional awards under the 2008 Plan. Outstanding awards under the 2008 Plan continue to be subject to the terms and conditions of the 2008 Plan.

The number of shares reserved for issuance under our 2017 Plan increases automatically on the first day of February of each calendar year during the term of the 2017 Plan by a number of shares of common stock equal to the lesser of (i) 5% of the total outstanding shares of our common stock as of the immediately preceding January 31 or (ii) a number of shares

determined by our board of directors. On February 1, 2020, the number of shares reserved for issuance under the 2017 Plan increased automatically by 14,758,388 additional shares. As of April 30, 2020, there were 23,000,734 shares of common stock reserved and available for future issuance under the Stock Plans.

Stock Options

Stock options granted generally have a maximum term of ten years from the grant date, are exercisable upon vesting unless otherwise designated for early exercise by the board of directors at the time of grant, and generally vest over a period of three to four years, with 25% vesting after one year and then ratably on a monthly basis for the remaining two to three years.

The following table summarizes stock option activity and related information under the Stock Plans:


	Options Outstanding
	Number of Shares	Weighted-Average Exercise Price		Weighted-Average Remaining Contractual Term (Years)	Aggregate Intrinsic Value (in thousands)




Balance — January 31, 2020	13,530,363	$	5.96	2.1	$	70,057

Exercised	(154,169)	3.15		—	—
Canceled	(251,319)	12.97		—	—
Balance — April 30, 2020	13,124,875	5.86		1.7	48,971

The total intrinsic value of stock options exercised during the three months ended April 30, 2020 and 2019 was $0.8 million and $6.8 million, respectively. The intrinsic value is the difference between the current fair market value of the stock for accounting purposes at the time of exercise and the exercise price of the stock option. As we have accumulated net operating losses, no future tax benefit related to stock option exercises has been recognized.

The unamortized stock-based compensation expense for stock options of $0.2 million as of April 30, 2020 will be recognized over the average remaining vesting period of 0.6 years.

Restricted Stock Units

We issue restricted stock units (RSUs) to employees and directors under the Stock Plans. For new employee grants, the RSUs generally meet the service-based condition over a four-year period, with 25% met after one year and then ratably on a quarterly basis for the remaining three years. For continuing employee grants, the RSUs generally meet the service-based condition pro-rata quarterly over a period of three years to four years.

The following table summarizes RSU activity and related information under the Stock Plans:


	Restricted Stock Units Outstanding
	Number of RSUs	Weighted-Average Grant Date Fair Value Per Share




Balance — January 31, 2020	38,583,994	$	10.85
Granted	5,500,804	9.00
Canceled	(1,638,338)	11.24
Vested and converted to shares	(5,851,821)	9.81
Balance — April 30, 2020	36,594,639	10.72

The unamortized stock-based compensation expense for RSUs of $346.8 million as of April 30, 2020 will be recognized over the average remaining vesting period of 2.3 years.

Employee Stock Purchase Plan

In March 2017, we adopted our 2017 Employee Stock Purchase Plan (ESPP). The ESPP became effective on April 27, 2017, the effective date of our initial public offering. Each offering period consists of a six-month purchase period (commencing each June 21 and December 21).

We initially reserved 3,000,000 shares of our common stock for issuance under our ESPP. The number of shares reserved for issuance under our ESPP increases automatically on February 1 of each of the first 10 calendar years following the first offering date by the number of shares equal to the lesser of (i) 1% of the total outstanding shares of our common stock as of the immediately preceding January 31 (rounded to the nearest whole share) or (ii) a number of shares of our common stock determined by our board of directors. On February 1, 2020, the number of shares reserved for issuance under the ESPP increased automatically by 2,951,677 additional shares. As of April 30, 2020, the total number shares available for grant under the ESPP was 5,857,371 shares.

As of April 30, 2020, $7.3 million has been withheld on behalf of employees for a future purchase under the ESPP and is recorded in accrued compensation in our condensed consolidated balance sheets. See Note 6 for additional information.