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Stock-Based Awards (Tables)
6 Months Ended
Jun. 30, 2019
Share-based Payment Arrangement [Abstract]  
Summary of Stock Option Activity
The following table summarizes the Company’s stock option activity for the six months ended June 30, 2019 (in thousands, except per share and term information):
 
 
Shares
 
Weighted-
Average
Exercise
Price
 
Weighted-
Average
Remaining
Contractual
Term
 
Aggregate
Intrinsic
Value (1)
Outstanding, December 31, 2018
3,828

 
$
32.41

 
4.1
 
$
70,436

Granted
—

 
—

 
 
 
 
Exercised
(270
)
 
37.59

 
 
 
 
Forfeited
(32
)
 
47.50

 
 
 
 
Outstanding, June 30, 2019
3,526

 
$
31.88

 
3.6
 
$
91,853

 
 
Shares
 
Weighted-
Average
Exercise
Price
 
Weighted-
Average
Remaining
Contractual
Term
 
Aggregate
Intrinsic
Value (1)
Exercisable at June 30, 2019
3,511

 
$
31.87

 
3.6
 
$
91,494

Vested and expected to vest at June 30, 2019
3,526

 
31.88

 
3.6
 
91,839


(1)
Based on the Company’s closing stock price of $57.93 on June 30, 2019 and $50.43 on December 31, 2018.

Schedule of Issuances of Awards Under New Compensation Award Structure
The following table summarizes the Company’s issuances of awards under the new compensation award structure:
Grant Date
Performance Measures
Vesting Term
Performance Period
# of Shares at Target
# of Shares at Maximum
Grant Date Fair Value per share
# of Shares Outstanding at Target (2)
# of Shares Outstanding at Maximum (2)
March 2017
(a) the Company meeting certain revenue and cash flow targets through December 31, 2019 and (b) the recipient continuing to provide services to the Company through the end of March 2020
Three years
Fiscal years 2017, 2018 and 2019
185,270

555,810

$
41.73

141,540

424,620

February 2018
(a) the Company meeting certain combined constant currency subscription revenue growth and unlevered cash flow margin targets for the year ending December 31, 2020 and (b) the recipient continuing to provide services to the Company through the end of February 2021
Three years
Fiscal year 2020
121,764

304,410

$
40.64

121,764

304,410

February 2018
(a) the Company meeting certain combined constant currency subscription revenue growth and unlevered cash flow margin targets for each of the years ending December 31, 2020, December 31, 2021, and December 31, 2022 and (b) the recipient continuing to provide services to the Company through each respective vest date at the end of February 2020, 2021 and 2022
Five years
Fiscal years 2020, 2021 and 2022 (1)
411,412

1,028,530

$
40.64

411,412

1,028,530

April 2018
(a) the Company meeting certain combined constant currency subscription revenue growth and unlevered cash flow margin targets for the year ending December 31, 2020 and (b) the recipient continuing to provide services to the Company through the beginning of April 2021
Three years
Fiscal year 2020
3,572

8,930

$
39.54

—

—

April 2018
(a) the Company meeting certain combined constant currency subscription revenue growth and unlevered cash flow margin targets for each of the years ending December 31, 2020, December 31, 2021, and December 31, 2022 and (b) the recipient continuing to provide services to the Company through each respective vest date at the beginning of April 2020, 2021 and 2022
Five years
Fiscal years 2020, 2021 and 2022 (1)
53,572

133,930

$
39.54

11,794

29,485


Grant Date
Performance Measures
Vesting Term
Performance Period
# of Shares at Target
# of Shares at Maximum
Grant Date Fair Value per share
# of Shares Outstanding at Target (2)
# of Shares Outstanding at Maximum (2)
February 2019
(a) the Company meeting certain combined constant currency subscription revenue growth and unlevered cash flow margin targets for the year ending December 31, 2021 and (b) the recipient continuing to provide services to the Company through the beginning of February 2022
Three years
Fiscal year 2021
13,178

32,945

$
58.23

13,178

32,945

February 2019
(a) the Company meeting certain combined constant currency subscription revenue growth and unlevered cash flow margin targets for the year ending December 31, 2021 and (b) the recipient continuing to provide services to the Company through the beginning of February 2022
Three years
Fiscal year 2021
80,559

201,398

$
57.27

80,559

201,398

March 2019
(a) the Company meeting certain combined constant currency subscription revenue growth and unlevered cash flow margin targets for the year ending December 31, 2021 and (b) the recipient continuing to provide services to the Company through the beginning of February 2022
Three years
Fiscal year 2021
43,136

107,835

$
56.15

43,136

107,835

June 2019
(a) the Company meeting certain combined constant currency subscription revenue and unlevered cash flow margin targets for the year ending December 31, 2021 and (b) the recipient continuing to provide services to the Company through the beginning of February 2022
Three years
Fiscal year 2021
19,143

47,857

$
54.84

19,143

47,857


(1)
One-third of the total eligible shares shall vest on each of the third, fourth and fifth anniversaries of the grant date. This award is a one-time equity award intended to cover expected grant levels over a three-year period. In exchange, the Compensation Committee does not plan to grant any additional equity awards to recipients of this award until 2021.
(2)
Excludes an aggregate of 244,565 shares at the maximum level and 89,080 shares at the target level of achievement that were forfeited due to termination of employment as of June 30, 2019.

Summary of Stock-based Compensation Expense
Stock-based compensation expense related to stock options, restricted stock units, the ESPP and performance-based restricted stock units is included in the following line items in the accompanying Condensed Consolidated Statements of Operations for the three and six months ended June 30, 2019 and 2018 (in thousands): 
 
Three Months Ended
 
Six Months Ended
 
June 30,
 
June 30,
 
2019
 
2018
 
2019
 
2018
Cost of revenue
$
1,786

 
$
1,021

 
$
2,922

 
$
2,023

Sales and marketing
6,809

 
6,545

 
12,856

 
12,791

Research and development
4,319

 
2,417

 
8,515

 
4,725

General and administrative
6,237

 
5,300

 
11,903

 
9,787

Restructuring
—

 
749

 
—

 
6,185

Total
$
19,151

 
$
16,032

 
$
36,196

 
$
35,511