Stock-based Awards

9 Months Ended

Sep. 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 nine months ended September 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	2,115,973		6.95
Exercised	(363,609	)	7.84
Forfeited/expired	(4,983,186	)	12.72
Outstanding at September 30, 2019	10,883,829		$	11.25	5.6

At September 30, 2019, total remaining stock-based compensation expense for unvested stock option awards was $15.3 million, which is expected to be recognized over a weighted-average period of 2.3 years. For the three months ended September 30, 2019 and 2018, the Company recorded stock-based compensation expense for stock option awards of $1.9 million and $4.2 million, respectively. For the nine months ended September 30, 2019 and 2018, the Company recorded stock-based compensation expense for stock option awards of $11.9 million and $12.6 million, respectively.

Restricted Stock Units

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

	Number of Shares		Weighted- Average Grant Date Fair Value
Non-vested — December 31, 2018	5,375,963		$	11.01
Granted	5,018,710		6.53
Vested	(2,252,523	)	9.54
Forfeited	(1,756,835	)	9.79
Non-vested — September 30, 2019	6,385,315		$	8.34

At September 30, 2019, total remaining stock-based compensation expense for non-vested restricted stock units was $50.1 million, which is expected to be recognized over a weighted-average period of 2.8 years. The Company recorded $5.3 million and $6.1 million in stock-based compensation expense for restricted stock units for the three months ended September 30, 2019 and 2018, respectively. The Company recorded $19.5 million and $15.7 million in stock-based compensation for restricted stock units for the nine months ended September 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 condensed consolidated statements of comprehensive loss (in thousands):

	Three Months Ended September 30,				Nine Months Ended September 30,
	2019		2018		2019		2018
Cost of revenue	$	549	$	469	$	1,601	$	1,210
Sales and marketing	2,697		3,852		10,885		10,522
Technology and development	1,615		2,829		7,024		7,880
General and administrative	2,330		3,097		11,872		8,704
Total stock-based compensation expense	7,191		10,247		31,382		28,316
Amount capitalized to internal software use	431		551		1,409		1,358
Total stock-based compensation cost	$	7,622	$	10,798	$	32,791	$	29,674

 

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 during the second quarter of 2019 and for the nine months ended September 30, 2019.