Stock-based Awards

6 Months Ended

Jun. 30, 2019

Disclosure of Compensation Related Costs, Share-based Payments [Abstract]

Stock based awards

Stock-based Awards

Stock Options

A summary of the Company’s stock option activity for the six months ended June 30, 2019 is as follows:

	Number of Options		Weighted-Average Exercise Price		Weighted-Average Remaining Contractual Life
					(in years)
Outstanding at December 31, 2018	14,114,651		$	12.32	7.0
Granted	2,022,047		7.06
Exercised	(355,147	)	7.98
Forfeited/expired	(2,701,845	)	12.96
Outstanding at June 30, 2019	13,079,706		$	11.50	6.8

At June 30, 2019, total remaining stock-based compensation expense for unvested stock option awards was $17.6 million, which is expected to be recognized over a weighted-average period of 2.5 years. For the three months ended June 30, 2019 and 2018, the Company recorded stock-based compensation expense for stock option awards of $6.9 million and $3.8 million, respectively. For the six months ended June 30, 2019 and 2018, the Company recorded stock-based compensation expense for stock option awards of $10.0 million and $8.4 million, respectively.

Restricted Stock Units

Activity in connection with restricted stock units is as follows for the six months ended June 30, 2019:

	Number of Shares		Weighted- Average Grant Date Fair Value
Non-vested — December 31, 2018	5,375,963		$	11.01
Granted	4,498,063		6.80
Vested	(1,704,577	)	9.63
Forfeited	(1,468,517	)	9.91
Non-vested — June 30, 2019	6,700,932		$	8.77

At June 30, 2019, total remaining stock-based compensation expense for non-vested restricted stock units was $56.3 million, which is expected to be recognized over a weighted-average period of 3.0 years. The Company recorded $8.7 million and $5.2 million in stock-based compensation expense for restricted stock units for the three months ended June 30, 2019 and 2018, respectively. The Company recorded $14.2 million and $9.6 million in stock-based compensation for restricted stock units for the six months ended June 30, 2019 and 2018, respectively.

Stock-based Compensation Cost

The Company recorded stock-based compensation cost relating to stock options and restricted stock units in the following categories on the accompanying consolidated statements of comprehensive loss (in thousands):

	Three Months Ended   June 30,				Six Months Ended   June 30,
	2019		2018		2019		2018
Cost of revenue	$	553	$	443	$	1,052	$	741
Sales and marketing	4,716		3,543		8,188		6,670
Technology and development	3,463		2,698		5,409		5,051
General and administrative	6,824		2,288		9,542		5,607
Total stock-based compensation expense	15,556		8,972		24,191		18,069
Amount capitalized to internal software use	505		473		978		807
Total stock-based compensation cost	$	16,061	$	9,445	$	25,169	$	18,876

 

As referenced in Note 7, certain executive-level employees, including the Company’s former chief executive officer, separated from the Company in the second quarter of 2019. Benefits provided associated with these terminations include severance payments, acceleration of certain equity awards and extension of the exercise period for certain vested stock options. As a result of these termination benefits, the Company recognized $7.2 million in additional stock-based compensation expense for the three and six months ended June 30, 2019.