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Stock-based Compensation Expense (Tables)
3 Months Ended
Apr. 30, 2019
Disclosure of Compensation Related Costs, Share-based Payments [Abstract]  
Schedule of stock options roll forward
A summary of stock option activity for the three months ended April 30, 2019 is as follows:
 
Number of shares (in millions)
 
Weighted average exercise price per share
 
Weighted average remaining contractual term (in years)
 
Aggregate intrinsic value (1) (in millions)
Options outstanding at January 31, 2019
0.8

 
$
23.95

 
 
 
 
Exercised
(0.1
)
 
24.72

 
 
 
 
Options outstanding at April 30, 2019
0.7

 
$
23.92

 
7.5
 
$
115.2

Options vested and exercisable at April 30, 2019
0.2

 
$
34.91

 
3.5
 
$
22.7

Shares available for grant at April 30, 2019

 
 
 
 
 
 
_______________
(1)
Represents the total pre-tax intrinsic value, based on Autodesk’s closing stock price of $178.21 per share as of April 30, 2019.
Intrinsic value of options exercised
The following table summarizes information about the pre-tax intrinsic value of options exercised during the three months ended April 30, 2019 and 2018:
(in millions)
Three months ended April 30,
 
2019
 
2018
Pre-tax intrinsic value of options exercised (1)
$
8.4

 
$
3.4

——————
(1)
The intrinsic value of options exercised is calculated as the difference between the exercise price of the option and the market value of the stock on the date of exercise.
Schedule of summary of restricted stock activity
A summary of restricted stock activity for the three months ended April 30, 2019, is as follows:
 
 
Unvested
restricted
stock units
 
Weighted
average grant
date fair value
per share
 
(in thousands)
 
 
Unvested restricted stock units at January 31, 2019
4,287.4

 
$
120.07

Granted
904.8

 
157.69

Vested
(429.6
)
 
117.08

Canceled/Forfeited
(104.5
)
 
123.87

        Performance Adjustment (1)
23.8

 
156.69

Unvested restricted stock units at April 30, 2019
4,681.9

 
$
127.70


 _______________
(1)
Based on Autodesk's financial results and relative total stockholder return for the fiscal 2019 performance period. The performance stock units were attained at rates ranging from 105.2% to 122.5% of the target award.

Schedule of summary of the ESPP activity
A summary of the ESPP activity for the three months ended April 30, 2019 and 2018, is as follows:

 
Three months ended April 30,
 
2019
 
2018
Issued shares (in millions)
0.5

 
0.5

Average price of issued shares
$
99.46

 
$
88.45

Weighted average grant date fair value of awards granted under the ESPP (1)
$
52.41

 
$
37.64

 _______________
(1)
Calculated as of the award grant date using the Black-Scholes Merton (“BSM") option pricing model.
Schedule of stock-based compensation expense
The following table summarizes stock-based compensation expense for the three months ended April 30, 2019 and 2018, respectively, as follows:
 
 
Three months ended April 30,
 
2019
 
2018
Cost of subscription and maintenance revenue
$
3.6

 
$
2.7

Cost of other revenue
1.3

 
0.8

Marketing and sales
32.5

 
24.0

Research and development
26.7

 
17.8

General and administrative
11.1

 
9.1

Stock-based compensation expense related to stock awards and ESPP purchases
75.2

 
54.4

Tax benefit
(0.2
)
 
(0.4
)
Stock-based compensation expense related to stock awards and ESPP purchases, net of tax
$
75.0

 
$
54.0


Schedule of assumptions to estimate the fair value of stock-based awards Autodesk uses the following assumptions to estimate the fair value of stock-based awards:
 
 
Three months ended April 30, 2019

Three months ended April 30, 2018
 
Performance Stock Unit

ESPP

Performance Stock Unit

ESPP
Range of expected volatilities
36.3%

36.6 - 39.7%

35.7%

33.5 - 37.5%
Range of expected lives (in years)
N/A

.5 - 2.0

N/A

0.5 - 2.0
Expected dividends
—%

—%

—%

—%
Range of risk-free interest rates
2.5%

2.4 - 2.5%

2.0%

1.9 - 2.3%