Stock-based Awards

9 Months Ended

Sep. 30, 2020

Share-based Payment Arrangement [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, 2020 is as follows:

	Number of Options	Weighted-Average Exercise Price		Weighted-Average Remaining Contractual Life
				(in years)
Outstanding at December 31, 2019	10,625,980	$	11.22	5.2
Granted	2,060,028	3.02
Exercised	(39,695)	2.12
Forfeited/expired	(1,739,430)	12.13
Outstanding at September 30, 2020	10,906,883	$	9.56	5.2

At September 30, 2020, total remaining stock-based compensation expense for unvested stock option awards was $8.8 million, which is expected to be recognized over a weighted-average period of 2.4 years. For the three months ended September 30, 2020 and 2019, the Company recorded stock-based compensation expense for stock option awards of $1.3 million and $1.8 million, respectively. For the nine months ended September 30, 2020 and 2019, the Company recorded stock-based compensation expense for stock option awards of $4.3 million and $11.6 million, respectively.

Restricted Stock Units

Activity in connection with restricted stock units is as follows for the nine months ended September 30, 2020:

	Number of Shares	Weighted- Average Grant Date Fair Value
Non-vested — December 31, 2019	5,890,992	$	7.96
Granted	6,118,702	2.91
Vested	(2,453,805)	3.43
Forfeited	(1,476,016)	7.38
Non-vested — September 30, 2020	8,079,873	$	4.71

At September 30, 2020, total remaining stock-based compensation expense for non-vested restricted stock units was $33.4 million, which is expected to be recognized over a weighted-average period of 2.3 years. The Company recorded $4.3 million and $5.0 million in stock-based compensation expense for restricted stock units for the three months ended September 30, 2020 and 2019, respectively. The Company recorded $13.4 million and $18.7 million in stock-based compensation expense for restricted stock units for the nine months ended September 30, 2020 and 2019, 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 income (loss) (in thousands):

	Three Months Ended September 30,				Nine Months Ended September 30,
	2020		2019		2020		2019
Cost of revenue	$	108	$	321	$	463	$	956
Sales and marketing	1,816		2,604		6,256		10,588
Technology and development	1,184		1,574		3,730		6,906
General and administrative	2,499		2,306		7,183		11,810
Total stock-based compensation expense	5,607		6,805		17,632		30,260
Amount capitalized to internal software use	293		394		992		1,304
Total stock-based compensation cost	$	5,900	$	7,199	$	18,624	$	31,564

For the nine months ended September 30, 2019, the Company recognized $7.2 million in additional stock-based compensation expense associated with the departures of the Company’s former chief executive officer and certain other executive-level employees.