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Equity and Equity Compensation Plans (Tables)
 6 Months Ended
Jun. 30, 2023
Share-Based Payment Arrangement [Abstract]  
Schedule of Reserved Shares of Common Stock
We have reserved shares of common stock for future issuance under our 2017 EIP as follows:
June 30, 2023December 31, 2022
Stock options issued and outstanding2,683,718 3,282,789 
Restricted stock units outstanding15,590,985 15,731,632 
Shares available for future equity grants11,106,336 7,951,616 
Total shares reserved for future issuance29,381,039 26,966,037 
We have reserved shares of common stock for future issuance under our ESPP as follows:
Six Months Ended June 30, 2023Year Ended
December 31, 2022
Shares available for issuance at beginning of period4,695,3615,865,467
Shares issued during the period(1,150,703)(1,170,106)
Total shares available for future issuance at end of period3,544,6584,695,361
Schedule of Stock Option Activity Option activity for the six months ended June 30, 2023 was as follows:
Number of OptionsWeighted-Average Exercise PriceWeighted-Average Remaining Contractual Life (Years)Aggregate Intrinsic Value
Outstanding as of January 1, 20233,282,789$9.10 2.90$1,145 
Options exercised(563,164)2.56 
Options expired(35,907)9.93 
Outstanding as of June 30, 2023
2,683,71810.46 2.899,783 
Options exercisable as of June 30, 2023
2,683,71810.46 2.899,783 
Schedule of Nonvested Restricted Stock Units Activity Restricted stock unit activity for the six months ended June 30, 2023 was as follows:
Restricted Stock UnitsWeighted-Average Grant-Date Fair Value
Outstanding as of January 1, 202315,731,632 $11.53 
Granted4,614,736 9.41 
Vested(3,568,639)13.18 
Forfeited or canceled(1,186,744)12.03 
Outstanding or deferred as of June 30, 2023(1)
15,590,985 10.49 
(1) Starting with the restricted stock units granted to them in June 2019, our non-employee directors have the option to defer the issuance of common stock receivable upon vesting of such restricted stock units until 60 days following the day they are no longer providing services to us or, if earlier, upon a change in control transaction. The amount reported as vested excludes restricted stock units that have vested but whose settlement into shares has been deferred. The amount reported as outstanding or deferred as of June 30, 2023 includes these restricted stock units. As no further conditions exist to prevent the issuance of the shares of common stock underlying these restricted stock units, the shares are included in basic and diluted weighted shares outstanding used to calculate net loss per share attributable to common stock. The amount of shares whose issuance have been deferred is not considered material and is not reported separately from stock-based compensation in our consolidated statements of changes in mezzanine equity and stockholders’ equity.
Schedule of Allocation of Share-based Compensation Costs Stock-based compensation expense associated with the PSUs was as follows:
Three Months Ended June 30,Six Months Ended June 30,
2023202220232022
PSU expense$1,731 $976 $3,380 $1,669 
Expense due to reassessment of achievement related to prior periods(586)— (390)— 
Total expense$1,145 $976 $2,990 $1,669 
Stock-based compensation, net of forfeitures and the amount capitalized in website and software development costs were as follows:
Three Months Ended June 30,Six Months Ended June 30,
2023202220232022
Cost of revenue$3,001 $3,615 $7,136 $6,605 
Technology and development(1)
8,241 6,768 16,368 13,877 
Marketing1,254 894 2,499 1,937 
General and administrative5,025 4,009 10,345 8,118 
Stock-based compensation from continuing operations17,521 15,286 36,348 30,537 
Stock-based compensation from discontinued operations(1)
31 1,527 234 3,064 
Total stock-based compensation$17,552 $16,813 $36,582 $33,601 
(1) Net of $1,070 and $919 of stock-based compensation that was capitalized in the three months ended June 30, 2023 and 2022, respectively, and $2,204 and $2,053 for the six months ended June 30, 2023 and 2022, respectively.