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Stock-based Compensation Expense (Tables)
6 Months Ended
Jul. 31, 2020
Share-based Payment Arrangement [Abstract]  
Schedule of summary of restricted stock activity
A summary of restricted stock activity for the six months ended July 31, 2020, is as follows:
 
Unvested
restricted
stock units
 
Weighted
average grant
date fair value
per share
 
(in thousands)
 
 
Unvested restricted stock units at January 31, 2020
4,732.3

 
$
147.24

Granted
867.8

 
176.50

Vested
(818.5
)
 
147.68

Canceled/Forfeited
(123.1
)
 
148.02

        Performance Adjustment (1)
15.4

 
166.97

Unvested restricted stock units at July 31, 2020
4,673.9

 
$
152.44


 _______________
(1)
Based on Autodesk's financial results and relative total stockholder return for the fiscal 2020 performance period. The performance stock units were attained at rates ranging from 96.6% to 101.1% of the target award.

Schedule of summary of the ESPP activity
A summary of the ESPP activity for the six months ended July 31, 2020 and 2019, is as follows:
 
Six Months Ended July 31,
 
2020
 
2019
Issued shares (in millions)
0.5

 
0.5

Average price of issued shares
$
122.54

 
$
99.46

Weighted average grant date fair value of awards granted under the ESPP (1)
$
45.70

 
$
52.41

 _______________
(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 and six months ended July 31, 2020 and 2019, respectively, as follows:
 
Three Months Ended July 31,
 
Six Months Ended July 31,
(in millions)
2020
 
2019
 
2020
 
2019
Cost of subscription and maintenance revenue
$
4.2

 
$
3.4

 
$
7.9

 
$
7.0

Cost of other revenue
1.5

 
1.4

 
3.0

 
2.7

Marketing and sales
43.4

 
36.0

 
84.1

 
68.5

Research and development
35.3

 
30.8

 
68.2

 
57.5

General and administrative
11.5

 
16.6

 
30.9

 
27.7

Stock-based compensation expense related to stock awards and ESPP purchases
95.9

 
88.2

 
194.1

 
163.4

Tax benefit
(0.2
)
 
(0.1
)
 
(0.3
)
 
(0.3
)
Stock-based compensation expense related to stock awards and ESPP purchases, net of tax
$
95.7

 
$
88.1

 
$
193.8

 
$
163.1


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:
 
Six Months Ended July 31, 2020
 
Six Months Ended July 31, 2019
 
Performance Stock Units (1)
 
ESPP (1)
 
Performance Stock Units (1)
 
ESPP (1)
Range of expected volatilities
50.7%
 
39.4 - 45.8%
 
36.3%
 
36.6 - 39.7%
Range of expected lives (in years)
N/A
 
0.5 - 2.0
 
N/A
 
0.5 - 2.0
Expected dividends
—%
 
—%
 
—%
 
—%
Range of risk-free interest rates
0.3%
 
0.3 - 0.5%
 
2.5%
 
2.4 - 2.5%

——————
(1)
There were no performance stock units or ESPP awards granted during the three months ended July 31, 2020 and 2019, where the fair value was estimated by a Monte Carlo simulation model or a BSM option pricing model, respectively.