Stock-based Compensation Expense (Tables)

A summary of stock option activity for the nine months ended October 31, 2015 is as follows:



	Number of Shares		Weighted average exercise price per share		Weighted average remaining contractual term	Aggregate Intrinsic Value (2)
	(in millions)				(in years)	(in millions)
Options outstanding at January 31, 2015	2.7		$	34.46
Granted (1)	—		—
Exercised	(0.7	)	31.43
Canceled/Forfeited	—		—
Options vested, exercisable and outstanding at October 31, 2015	2.0		$	35.63	3.8	$	38.4
Options available for grant at October 31, 2015	20.8

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(1)	Autodesk did not grant stock options in the nine months ended October 31, 2015.


(2)	Represents the total pre-tax intrinsic value, based on Autodesk’s closing stock price of $55.19 per share as of October 31, 2015, which would have been received by the option holders had all option holders exercised their options as of that date.

The following table summarizes information about the pre-tax intrinsic value of options exercised during the three and nine months ended October 31, 2015 and 2014:



	Three Months Ended October 31,				Nine Months Ended October 31,
	2015		2014		2015		2014
Pre-tax intrinsic value of options exercised (1)	$	2.6	$	10.3	$	20.0	$	54.5

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(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.

The following table summarizes information about options vested, exercisable and outstanding at October 31, 2015:



	Number of Shares (in millions)	Weighted average contractual life (in years)	Weighted average exercise price		Aggregate intrinsic value (1) (in millions)
Range of per-share exercise prices:
$12.31 - $29.49	0.7		$	24.62
$29.50 - $41.62	0.8		39.68
$42.39 - $43.81	0.5		43.80
Options vested, exercisable and outstanding	2.0	3.8	$	35.63	$	38.4

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(1)	Represents the total pre-tax intrinsic value, based on Autodesk’s closing stock price of $55.19 per share as of October 31, 2015, which would have been received by the option holders had all option holders exercised their options as of that date.

A summary of restricted stock unit activity for the nine months ended October 31, 2015 is as follows:



	Unvested Restricted Stock Units		Weighted average grant date fair value per share
	(in thousands)
Unvested restricted stock units at January 31, 2015	7,801.3		$	48.46
Granted	3,268.8		50.42
Vested	(2,949.1	)	44.61
Canceled/Forfeited	(364.6	)	49.86
Performance Adjustment (1)	34.6		54.92
Unvested restricted stock units at October 31, 2015	7,791.0		$	50.60

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(1)	Based on Autodesk's financial results for fiscal 2015, 2014 and 2013 performance period. The performance stock units were earned at 113.8%, 65.8%, and 92.3% of the target award, respectively. The vesting of the 2013 performance stock units was subject to the holders satisfying the remaining service condition of the awards, which ended in March 2015.

The following table summarizes stock-based compensation expense for the three and nine months ended October 31, 2015 and 2014, respectively, as follows:



	Three Months Ended October 31,
	2015		2014
Cost of license and other revenue	$	1.7	$	1.2
Cost of subscription	1.5		1.1
Marketing and sales	22.3		19.4
Research and development	17.5		14.7
General and administrative	7.2		6.7
Stock-based compensation expense related to stock awards and ESPP purchases	50.2		43.1
Tax benefit	—		(11.7		)
Stock-based compensation expense related to stock awards and ESPP purchases, net of tax	$	50.2	$	31.4

	Nine Months Ended October 31,
	2015		2014
Cost of license and other revenue	$	4.4	$	3.2
Cost of subscription	4.1		2.9
Marketing and sales	61.3		51.0
Research and development	49.9		39.3
General and administrative	21.4		20.1
Stock-based compensation expense related to stock awards and ESPP purchases	141.1		116.5
Tax benefit	—		(31.3		)
Stock-based compensation expense related to stock awards and ESPP purchases, net of tax	$	141.1	$	85.2

Autodesk uses the following assumptions to estimate the fair value of stock-based awards:



	Three Months Ended October 31, 2015			Three Months Ended October 31, 2014
		Performance Stock Unit (1)	ESPP	Performance Stock Unit (1)	ESPP
Range of expected volatilities		N/A	29%	N/A	29 - 30%
Range of expected lives (in years)		N/A	0.5 - 2.0	N/A	0.5 - 2.0
Expected dividends		N/A	—%	N/A	—%
Range of risk-free interest rates		N/A	0.2 - 0.7%	N/A	0.0 - 0.6%
	Nine Months Ended October 31, 2015			Nine Months Ended October 31, 2014
		Performance Stock Unit	ESPP	Performance Stock Unit	ESPP
Range of expected volatilities		27%	28 - 29%	30%	29 - 33%
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		0.2%	0.1 - 0.7%	0.1%	0.0 - 0.6%

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(1)	Autodesk did not grant PSUs in the three months ended October 31, 2015 and 2014 that were subject to market conditions.