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Stock-Based Compensation
3 Months Ended
Sep. 30, 2019
Share-based Payment Arrangement [Abstract]  
Stock-Based Compensation Stock-Based Compensation 
Stock Compensation Accounting
The weighted average estimated fair value of option awards granted was $33.15 and $31.70 during the three months ended September 30, 2019 and 2018, respectively.
 
We utilized the Black-Scholes option valuation model with the following weighted average assumptions:
 
 
Three Months Ended
September 30,
 
2019
 
2018
Risk-free interest rate
1.5
%
 
2.8
%
Expected dividend yield
0.0
%
 
0.0
%
Expected life (in years)
4.5

 
4.6

Expected volatility factor
26.8
%
 
26.6
%

 
The stock-based compensation expense under all equity plans and its classification in the unaudited consolidated statements of operations for the three months ended September 30, 2019 and 2018 are as follows:
 
 
Three Months Ended
September 30,
 
2019
 
2018
 
(Dollars in Thousands)
Recorded as expenses:
 

 
 

Cost of maintenance
$
398

 
$
146

Cost of services and other
543

 
319

Selling and marketing
1,547

 
1,331

Research and development
2,102

 
2,295

General and administrative
4,685

 
4,774

Total stock-based compensation
$
9,275

 
$
8,865



A summary of stock option and restricted stock unit ("RSU") activity under all equity plans for the three months ended September 30, 2019 is as follows:
 
 
Stock Options
 
Restricted Stock Units
 
Shares
 
Weighted
Average
Exercise
Price
 
Weighted
Average
Remaining
Contractual
Term
(Years)
 
Aggregate
Intrinsic Value
(in 000’s)
 
Shares
 
Weighted
Average
Grant Date
Fair Value
Outstanding at June 30, 2019
1,304,017

 
$
60.33

 
6.94
 
$
83,388

 
793,718

 
$
98.38

Granted
292,790

 
133.15

 
 
 
 

 
247,823

 
133.15

Settled (RSUs)

 
 

 
 
 
 

 
(85,033
)
 
90.72

Exercised
(17,783
)
 
52.58

 
 
 
 

 

 
 

Cancelled / Forfeited
(4,836
)
 
73.94

 
 
 
 

 
(63,619
)
 
91.58

Outstanding at September 30, 2019
1,574,188

 
$
73.92

 
7.11
 
$
80,332

 
892,889

 
$
108.12

Vested and exercisable at September 30, 2019
907,522

 
$
52.41

 
5.79
 
$
64,385

 

 
 

Vested and expected to vest as of September 30, 2019
1,460,388

 
$
73.73

 
7.28
 
$
74,736

 
842,490

 
$
108.31


 
The weighted average grant-date fair value of RSUs granted was $133.15 and $115.17 during the three months ended September 30, 2019 and 2018, respectively. The total fair value of shares vested from RSU grants was $10.5 million and $9.9 million during the three months ended September 30, 2019 and 2018, respectively.
 
At September 30, 2019, the total future unrecognized compensation cost related to stock options was $16.1 million and is expected to be recorded over a weighted average period of 3.1 years.  At September 30, 2019, the total future unrecognized compensation cost related to RSUs was $53.3 million and is expected to be recorded over a weighted average period of 3.1 years.
 
The total intrinsic value of options exercised was $1.3 million and $6.1 million during the three months ended September 30, 2019 and 2018, respectively. We received cash proceeds from option exercises of $1.0 million and $4.1 million during the three months ended September 30, 2019 and 2018, respectively. We withheld withholding taxes on vested RSUs of $3.4 million and $3.3 million during the three months ended September 30, 2019 and 2018, respectively.
 
At September 30, 2019, common stock reserved for future issuance or settlement under equity compensation plans was 9.6 million shares.
Performance Awards
Beginning in fiscal 2019, we granted performance-based long-term incentive awards (“performance awards”) to certain of our executives, including our named executive officers. The performance period for each performance award is either of the following two-year periods: (i) fiscal year 2019 - fiscal year 2020, or (ii) fiscal year 2020 - fiscal year 2021.  Participants receive RSUs on the grant date associated with achievement of all performance targets. The performance targets for the performance awards are based on meeting double digit growth in annual spend, defined as an estimate of the annualized value of our portfolio of term license arrangements, as of a specific date, and the performance goals set out in the executive bonus plan for each fiscal year, such as free cash flow. If the performance targets are met during one of the two performance periods and the participant remains actively employed by us, the RSUs convert to time-based vesting wherein fifty percent of the awards immediately vest, and the remaining fifty percent are subject to additional service vesting over a three-year period.  In general, if the performance targets are not met, or if the participant is no longer actively employed by us prior to the performance targets being met, the participant forfeits all of the RSUs.

We record compensation expense for the performance awards based on the fair value of the awards, in an amount proportionate to the service time rendered by the participant, when it is probable that the achievement of the goals will be met. The total fair value of the performance awards was estimated using the closing price on the date of grant as well as the estimated probable achievement levels of the performance metrics.  If the performance-based conditions are not met, no compensation cost is recognized and any recognized compensation cost is reversed.  

As of September 30, 2019, we have granted 403,770 RSUs in connection with the performance awards.  As of September 30, 2019, all of the RSUs issued in connection with the performance awards are unvested and outstanding. No compensation expense was recognized during the three months ended September 30, 2019 and 2018

On August 2, 2019, 60,680 RSUs in connection with the performance awards were forfeited associated with the departure of an executive.

Employee Stock Purchase Plan

On July 26, 2018, our Board of Directors approved the Aspen Technology, Inc. 2018 Employee Stock Purchase Plan (the "ESPP"), which provides for the issuance of up to 250,000 shares of common stock to participating employees. The ESPP is intended to be a qualified employee stock purchase plan under Section 423 of the Internal Revenue Code of 1986, or the IRC.  The ESPP was approved at our Annual Meeting of Stockholders on December 7, 2018.  The ESPP currently provides for a purchase price equal to 85% of the lower of (a) the fair market value of the common stock on the first trading day of each ESPP offering period and (b) the fair market value of the common stock on the last day of the offering period. Our initial offering period was January 1, 2019 through June 30, 2019, and our current offering period is July 1, 2019 through December 31, 2019.

During the three months ended September 30, 2019, we recorded stock-based compensation expense of approximately $0.1 million associated with the ESPP. As of September 30, 2019, there were 236,961 shares of common stock available for issuance under the ESPP.