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Stockholders' Equity
9 Months Ended
Oct. 31, 2019
Disclosure of Compensation Related Costs, Share-based Payments [Abstract]  
Stockholders' Equity Stockholders’ Equity
Beginning in the fiscal quarter ended April 30, 2019, we implemented a new equity compensation program applicable to the vast majority of our employees but not applicable to our Chief Executive Officer (CEO). Prior to the adoption of the new equity compensation program, at the time of hire, our employees received a grant of RSUs that vested quarterly over four years and received additional equity from time to time thereafter. Under the new equity compensation program, the vast majority of our employees are granted both RSUs, which typically vest over a one-year period, and stock options, which typically vest over a four-year period.
Stock Option Activity
A summary of stock option activity for the nine months ended October 31, 2019 is as follows: 
 
Number
of shares
 
Weighted
average
exercise
price
 
Weighted
average
remaining
contractual
term (in years)
 
Aggregate
intrinsic
value
Options outstanding at January 31, 2019
12,961,397

 
$
19.43

 
5.4
 
$
1,161,695,032

Options granted
1,475,355

 


 
 
 
 
Options exercised
(1,225,746
)
 


 
 
 
 
Options forfeited/cancelled
(318,028
)
 


 
 
 
 
Options outstanding at October 31, 2019
12,892,978

 
$
33.25

 
5.2
 
$
1,401,940,929

Options vested and exercisable at October 31, 2019
6,704,980

 
$
5.96

 
3.4
 
$
911,013,694

Options vested and exercisable at October 31, 2019 and
expected to vest thereafter
12,892,978

 
$
33.25

 
5.2
 
$
1,401,940,929

 
 
 
 
 
 
 
 
 
During the three and nine months ended October 31, 2019, we granted 120,010 and 1,475,355 stock options, respectively, under the 2013 Equity Incentive Plan (2013 EIP). The options granted during the nine months ended October 31, 2019 reflects grants predominantly made in connection with our annual performance review cycle. The weighted average grant-date fair value of options granted was $64.07 and $59.00 for the three and nine months ended October 31, 2019, respectively.
As of October 31, 2019, there was $147.9 million in unrecognized compensation cost related to unvested stock options granted under the 2007 Stock Plan, 2012 Equity Incentive Plan and 2013 EIP. This cost is expected to be recognized over a weighted average period of 3.8 years.
As of October 31, 2019, we had authorized and unissued shares of common stock sufficient to satisfy exercises of stock options.
The total intrinsic value of options exercised was approximately $31.1 million and $166.9 million for the three and nine months ended October 31, 2019, respectively.
Restricted Stock Units
A summary of restricted stock unit (RSU) activity for the nine months ended October 31, 2019 is as follows:
 
Unreleased restricted
stock units
 
Weighted 
average grant
date fair value
Balance at January 31, 2019
2,359,132

 
$
54.73

RSUs granted
278,053

 
138.22

RSUs vested
(945,117
)
 
54.42

RSUs forfeited/cancelled
(163,375
)
 
59.59

Balance at October 31, 2019
1,528,693

 
$
69.59

 
 
 
 

During the three months ended October 31, 2019, we granted 51,995 RSUs under the 2013 EIP with a weighted-average grant date fair value of $150.53. During the nine months ended October 31, 2019, we granted 278,053 RSUs under the 2013 EIP with a weighted-average grant date fair value of $138.22.
As of October 31, 2019, there was a total of $94.9 million in unrecognized compensation cost related to unvested RSUs. This cost is expected to be recognized over a weighted-average period of approximately 1.8 years. The total intrinsic value of RSUs vested was $48.0 million and $136.0 million for the three and nine months ended October 31, 2019, respectively.
Stock-Based Compensation
Compensation expense related to share-based transactions, including equity awards to employees and non-employee directors, is measured and recognized in the condensed consolidated financial statements based on fair value. The grant date fair value of each option award is estimated on the grant date using the Monte Carlo simulation or Black-Scholes option-pricing model. The stock-based compensation expense is recognized using a straight-line basis over the requisite service periods of the awards, which is generally four to nine years. For RSUs, the grant date fair value is based on the closing price of our common stock on the grant date.
Our option-pricing model requires the input of subjective assumptions, including the fair value of the underlying common stock, the expected term of the option, the expected volatility of the price of our common stock, risk-free interest rates, and the expected dividend yield of our common stock. The assumptions used in our option-pricing model represent management’s best estimates. These estimates involve inherent uncertainties and the application of management’s judgment. If factors change and different assumptions are used, our stock-based compensation expense could be materially different in the future.
The following table presents the weighted-average assumptions used to estimate the grant date fair value of options granted during the periods presented:
 
Three months ended
October 31,
 
Nine months ended
October 31,
 
2019
 
2018
 
2019
 
2018
Volatility
41%
 
—%
 
41%
 
41%
Expected term (in years)
6.25
 
 
5.75 - 6.35
 
6.35
Risk-free interest rate
1.39% - 1.64%
 
—%
 
1.39% - 2.52%
 
2.73%
Dividend yield
—%
 
—%
 
—%
 
—%
 
 
 
 
 
 
 
 

During the fiscal year ended January 31, 2018, we granted 2,838,635 stock options to our CEO. The stock option award is made up of five separate tranches. The first tranche vests over time, while the remaining four tranches vest based on certain stock price targets (market conditions). The grant date fair values of each tranche were calculated using a Monte Carlo simulation model. We have based our expected term on the historical stock activity behavior of our CEO. The following table provides the assumptions used in the Monte Carlo simulation for each tranche granted:
Volatility
41
%
Expected term (in years)
10.00

Risk-free interest rate
2.53
%
Dividend yield
%
 
 

For the periods presented, we capitalized an immaterial amount of stock-based compensation as part of our internal-use software capitalization.