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Stockholders’ Equity and Stock Option Plans
 3 Months Ended
Mar. 31, 2023
Equity [Abstract]  
Stockholders’ Equity and Equity Incentive Plans Stockholders’ Equity and Equity Incentive Plans
Share Repurchases
In February 2023, the Company’s board of directors authorized the Company to repurchase up to $75 million of its Class A common stock (“2023 Repurchase Program”). As of March 31, 2023, $67.1 million remains available for repurchases. Shares are repurchased in a manner deemed in the best interest of the Company and its stockholders, dependent upon business, economic and market conditions, corporate and regulatory requirements, prevailing stock prices and other considerations.
In accordance with the authorization of the Company’s board of directors, during the three months ended March 31, 2023, we repurchased 586,830 aggregate shares of Class A common stock for $7.9 million.
Repurchases are executed from time to time, subject to general business and market conditions and other investment opportunities, through open market purchases or privately negotiated transactions, in accordance with Rule 10b-18 and/or Rule 10b5-1 of the Exchange Act. The 2023 Repurchase Program is scheduled to terminate on December 31, 2024.
Equity Incentive Plans
The Company maintains the 2020 Equity Incentive Plan (“2020 Plan”), pursuant to which the Company may grant stock options, restricted stock awards, stock appreciation rights, restricted stock units (“RSUs”), deferred stock units (“DSUs”) performance awards, and stock bonus awards. As of March 31, 2023, the Company has reserved 6,597,753 shares of Class A common stock for the issuance of awards under the 2020 Plan. These available shares will increase automatically on January 1 for each of the first ten calendar years during the term of the 2020 Plan by the number of shares equal to the lesser of five percent (5%) of the aggregate number of outstanding shares of all classes of the Company’s common stock outstanding as of the immediately preceding December 31, or a number as may be determined by the Company’s board of directors or compensation committee. No new awards were issued under the Company’s prior 2006 Plan or 2017 Plan (“Prior Plans”) after the effective date of the 2020 Plan. To the extent outstanding awards under the 2006 Plan and the 2017 Plan are forfeited, expire unexercised, or would otherwise have been returned to the share reserve under the Prior Plans, the shares of Class B common stock subject to such awards instead will be available for future issuance as Class A common stock under the 2020 Plan.
Stock Options
The following table summarizes stock option activity and related information under the Company’s equity incentive plans:
Stock Options
Number of Shares Underlying Outstanding OptionsWeighted-Average Exercise PriceWeighted Average Remaining Contractual Term (Years)Aggregate Intrinsic Value (in thousands)
Outstanding — December 31, 20226,476,239 $7.38 6.10$55,516 
Options granted1,313,004 15.40 
Options exercised(108,597)2.88 
Options canceled(2,570)6.14 
Options expired(15,538)$33.92 
Outstanding — March 31, 20237,662,538 $8.76 6.24$59,796 
Vested and exercisable — March 31, 20235,245,258 $5.27 5.23$53,940 
As of March 31, 2023, unrecognized stock-based compensation of $23.0 million related to unvested stock options will be recognized on a straight-line basis over a weighted average period of 2.76 years.
Restricted Stock Units
The following table summarizes RSU activity and related information under the Company’s 2020 Plan:
RSUs
Number of SharesWeighted-Average Grant Date Fair Value per Share
Unvested — December 31, 20221,581,982 $26.49 
Granted2,049,867 $16.07 
Vested(95,825)$29.92 
Canceled/Forfeited(26,512)$21.60 
Unvested — March 31, 20233,509,512 $20.35 
As of March 31, 2023, unrecognized stock-based compensation of $65.3 million related to unvested RSUs will be recognized on a straight-line basis over a weighted average period of 3.26 years.
2020 Employee Stock Purchase Plan
In November 2020, the Company’s board of directors adopted, and its stockholders approved, the 2020 Employee Stock Purchase Plan (“ESPP”), which became effective in connection with the Company’s IPO. A total of 500,000 shares of the Company’s Class A common stock were initially reserved for issuance under the ESPP.
The aggregate number of shares reserved for issuance under the ESPP will increase automatically on January 1st of each of the first ten calendar years during the term of the ESPP by the number of shares equal to the lesser of (a) 1% of the total outstanding shares of all classes of the Company’s common stock as of the immediately preceding December 31, and (b) such number of shares of common stock as determined by the Company’s board of directors. The aggregate number of shares issued over the term of the ESPP may not exceed 7,500,000 shares of Class A common stock. As of March 31, 2023, the Company had reserved 529,888 shares of its Class A common stock for issuance under the ESPP.
Under the ESPP, Class A common stock will be purchased for the accounts of employees participating in the ESPP on each purchase date at a price per share equal to 85% of the lesser of: (a) the fair market value on the offering date or (b) the fair market value on the purchase date. The ESPP provides for, at maximum, 27 month offering periods and each offering period may consist of one or more six-month purchase periods, whereby the latest offering period commenced on June 1, 2022, and the offering periods thereafter consist of two six-month purchase periods ending May 31, 2023. As of March 31, 2023, $0.7 million has been withheld on behalf of employees for a future purchase under the ESPP due to the timing of payroll deductions and is included in accrued liabilities. For the three months ended March 31, 2023, there were no shares of our Class A common stock purchased under the ESPP.
As of March 31, 2023, unrecognized stock-based compensation expense related to the ESPP was $0.1 million, which is expected to be recognized over a weighted-average period of 0.17 years.
Stock-Based Compensation
Total stock-based compensation expense recognized in the condensed consolidated statements of operations was as follows (in thousands):
Three Months Ended March 31,
20232022
Cost of revenue$316 $278 
Technology and development1,008 877 
Sales and marketing2,709 1,907 
General and administrative3,026 2,074 
Total stock-based compensation expense7,059 5,136 
Tax benefit from stock-based compensation(1,318)(831)
Total stock-based compensation expense, net of tax effect$5,741 $4,305