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Stock-Based Compensation
 12 Months Ended
Dec. 31, 2019
Share-based Payment Arrangement [Abstract]  
Stock-Based Compensation Stock-Based Compensation
In connection with its IPO, the Company implemented its 2014 Equity Incentive Plan, which governs equity awards made to employees and directors of the Company since the IPO. Prior to the IPO, the Company granted equity awards under its 2007 Stock Incentive Plan, which governs equity awards made to employees and contractors prior to the IPO. In November 2014, the Company approved the 2014 Inducement Grant Equity Incentive Plan (the "Inducement Plan"), which governs certain equity awards made to certain employees in connection with commencement of employment. In connection with the Company's acquisitions of Chango Inc. ("Chango"), iSocket, Inc. ("iSocket"), and nToggle, Inc. ("nToggle") it assumed the existing employee equity award plans, the 2009 Chango Stock Option Plan (the "Chango Plan"), the iSocket 2009 Equity Incentive Plan (the "iSocket Plan"), and the nToggle 2014 Equity Incentive Plan (the "nToggle Plan"). All compensatory equity awards outstanding at
December 31, 2019 were issued pursuant to the 2014 Equity Incentive Plan, the iSocket Plan, the Chango Plan, the nToggle Plan, the Inducement Plan, or the Company's 2007 Stock Incentive Plan.
The Company’s equity incentive plans provide for the grant of equity awards, including non-statutory or incentive stock options, restricted stock awards, and restricted stock units, to the Company's employees, officers, directors, and consultants. The Company's board of directors administers the plans. Options outstanding vest based upon continued service at varying rates, but generally over four years from issuance with 25% vesting after one year of service and the remainder vesting monthly thereafter. Restricted stock awards and restricted stock units vest at varying rates, typically approximately 25% vesting after approximately one year of service and the remainder vesting semi-annually thereafter. The restricted stock units granted in 2019 and 2018 included 1.8 million and 2.8 million, respectively, restricted stock units that vest 50% on each of the first and second anniversaries of the grant date. Restricted stock units granted in 2020 will typically have approximately 25% of the award vesting after approximately one year of service and the remainder vesting quarterly thereafter. Options, restricted stock awards, and restricted stock units granted under the plans accelerate under certain circumstances for certain participants upon on a change in control, as defined in the governing plan. No further awards were made under the iSocket Plan, the Chango Plan, or the nToggle Plan from the date of acquisition and no further awards were made under the 2007 Stock Incentive Plan since the IPO. Available shares under the iSocket Plan, the Chango Plan, and the nToggle Plan were rolled into the available share pool under the 2014 Equity Incentive Plan at the time of acquisition of each company, and available shares under the 2007 Stock Incentive Plan were rolled into the available share pool under the 2014 Equity Incentive Plan at the time of the IPO. An aggregate of 3,780,447 shares remained available for future issuance at December 31, 2019 under the plans. The 2014 Equity Incentive Plan has an evergreen provision pursuant to which the share reserve will automatically increase on January 1st of each year in an amount equal to 5% of the total number of shares of capital stock outstanding on December 31st of the preceding calendar year, although the Company’s board of directors may provide for a lesser increase, or no increase, in any year. The 2014 Inducement Grant Equity Incentive Plan has a provision pursuant to which the share reserve may be increased at the discretion of the Company's board of directors.
Stock Options
A summary of stock option activity for the year ended December 31, 2019 is as follows:

Shares Under Option
 
Weighted- Average Exercise Price
 
Weighted- Average Contractual Life
 
Aggregate Intrinsic Value

(in thousands)
 
 
 
 
 
(in thousands)
Outstanding at December 31, 2018
3,488

 
$
7.06

 
 
 
 
Granted
1,184

 
$
4.98

 
 
 
 
Exercised
(285
)
 
$
1.99

 
 
 
 
Expired
(47
)
 
$
13.36

 
 
 
 
Forfeited
(78
)
 
$
2.74

 
 
 
 
Outstanding at December 31, 2019
4,262

 
$
6.82

 
6.9 years
 
$
11,825

Exercisable at December 31, 2019
2,420

 
$
8.62

 
5.6 years
 
$
4,995


The total intrinsic value of options exercised during the year ended December 31, 2019 was $1.6 million. At December 31, 2019, the Company had unrecognized employee stock-based compensation expense relating to nonvested stock options of approximately $4.0 million, which is expected to be recognized over a weighted-average period of 2.6 years. The weighted-average grant date fair value per share of stock options granted during the year ended December 31, 2019 was $2.85. Total fair value of options vested during the year ended December 31, 2019 was $1.6 million.
The Company estimates the fair value of stock options that contain service and/or performance conditions using the Black-Scholes option pricing model. The weighted-average input assumptions used by the Company were as follows:
 
 
Year Ended
 
 
December 31, 2019
 
December 31, 2018
Expected term (in years)
 
6.1

 
6.0

Risk-free interest rate
 
2.55
%
 
2.67
%
Expected volatility
 
60
%
 
57
%
Dividend yield
 
—
%
 
—
%

Restricted Stock Awards
A summary of restricted stock activity for the year ended December 31, 2019 is as follows:
 
Number of Shares
 
Weighted-Average Grant Date Fair Value
 
(in thousands)
 
 
Nonvested shares of restricted stock outstanding at December 31, 2018
197

 
$
12.06

Granted
—

 
$
—

Canceled
(182
)
 
$
12.71

Vested
(13
)
 
$
13.74

Nonvested shares of restricted stock outstanding at December 31, 2019
2

 
$
13.49


The aggregate fair value of restricted stock awards with service conditions that vested during the year ended December 31, 2019 was $0.1 million. At December 31, 2019, the Company had unrecognized stock-based compensation expense for restricted stock awards with service conditions of $18.9 thousand, which is expected to be recognized over a weighted-average period of 0.4 years.
Restricted Stock Units
A summary of restricted stock unit activity for the year ended December 31, 2019 is as follows:
 
Number of Shares
 
Weighted-Average Grant Date Fair Value
 
(in thousands)
 
 
Nonvested restricted stock units outstanding at December 31, 2018
6,100

 
$
3.56

Granted
5,341

 
$
5.09

Canceled
(506
)
 
$
3.94

Vested
(2,858
)
 
$
3.82

Nonvested restricted stock units outstanding at December 31, 2019
8,077

 
$
4.46


The weighted-average grant date fair value per share of restricted stock units granted during the year ended December 31, 2019 was $5.09. The aggregate fair value of restricted stock units that vested during the year ended December 31, 2019 was $16.6 million. At December 31, 2019, the intrinsic value of nonvested restricted stock units was $65.9 million. At December 31, 2019, the Company had unrecognized stock-based compensation expense relating to nonvested restricted stock units of approximately $26.0 million, which is expected to be recognized over a weighted-average period of 2.1 years.
Employee Stock Purchase Plan
In November 2013, the Company adopted the Company's 2014 Employee Stock Purchase Plan ("ESPP"). The ESPP is designed to enable eligible employees to periodically purchase shares of the Company's common stock at a discount through payroll deductions of up to 10% of their eligible compensation, subject to any plan limitations. At the end of each six-month offering period, employees are able to purchase shares at a price per share equal to 85% of the lower of the fair market value of the Company's common stock on the first trading day of the offering period or on the last trading day of the offering period. Offering periods generally commence and end in May and November of each year.
As of December 31, 2019, the Company has reserved 1,891,813 shares of its common stock for issuance under the ESPP. The ESPP has an evergreen provision pursuant to which the share reserve will automatically increase on January 1st of each year in an amount equal to 1% of the total number of shares of capital stock outstanding on December 31st of the preceding calendar year, although the Company’s board of directors may provide for a lesser increase, or no increase, in any year.
Stock-Based Compensation Expense
Total stock-based compensation expense recorded in the consolidated statements of operations was as follows:  
 
Year Ended
 
December 31, 2019

December 31, 2018
 
(in thousands)
Cost of revenue
$
421

 
$
321

Sales and marketing
5,638

 
4,557

Technology and development
4,757

 
2,867

General and administrative
8,009

 
8,139

Restructuring and other exit costs
—

 
398

Total stock-based compensation expense
$
18,825

 
$
16,282