Stockholders' Equity (Deficit) and Equity Incentive Plans | (6) Stockholders’ Equity and Equity Incentive Plans Preferred stock In connection with the direct listing of the Company's Class A common stock on the Nasdaq Capital Market (the “Direct Listing”), on September 21, 2021, an amended and restated certificate of incorporation of the Company was filed with the Secretary of State of the State of Delaware, which authorized the issuance of 20 million shares of undesignated preferred stock with a par value of $ 0.00001 per share and rights and preferences, including voting rights, designated from time to time by the Company's board of directors. Common Stock The Company has two classes of common stock: Class A common stock and Class B common stock. The Company's amended and restated certificate of incorporation authorizes the issuance of 600 million shares of Class A common stock and 600 million shares of Class B common stock. The shares of Class A common stock and Class B common stock are identical, except with respect to voting, conversion, and transfer rights. Each share of Class A common stock is entitled to one vote . Each share of Class B common stock is entitled to five votes . Class A and Class B common stock each have a par value of $ 0.00001 per share, and are referred to as common stock throughout the notes to the condensed consolidated financial statements, unless otherwise noted. Holders of common stock are entitled to receive any dividends whenever funds are legally available and if declared by the Company's board of directors. Shares of Class B common stock may be converted to Class A common stock at any time at the option of the stockholder. Shares of Class B common stock will also automatically convert into one share of Class A common stock upon any transfer, except for certain permitted transfers described in the Company's amended and restated certificate of incorporation. In addition, each share of Class B common stock held by the Company's three cofounders (or any of such founder’s affiliates) will convert automatically into one share of Class A common stock on the earlier of: (i) the death or incapacity of such founder or (ii) the date that is six months following the date on which such founder is no longer an employee or director of the Company (unless such founder has rejoined the Company during such six-month period). Each outstanding share of the Company's Class B common stock will also convert automatically into one share of Class A common stock on the date that is six months following the date on which no founder is an employee or director of the Company (unless a founder has rejoined the Company during such six-month period). In addition, any transfer by a founder (or such founder’s affiliates) to one or more of the other founders (or such founders’ affiliates) will not result in the automatic conversion of such shares of Class B common stock to Class A common stock. Once converted into Class A common stock, the Class B common stock may not be reissued. The Company has reserved shares of its common stock as follows: As of As of 2014 Stock Option and Grant Plan and 2021 Incentive Award Plan: Equity plan stock options outstanding 14,941,912 16,767,752 RSUs outstanding 11,661,484 9,914,125 Shares available for future issuance 18,268,935 16,774,634 2021 Employee Stock Purchase Plan: Shares available for future issuance 4,251,616 3,411,791 Total reserved shares 49,123,947 46,868,302 Equity Incentive Plans 2014 Stock Option and Grant Plan In December 2014, the Company adopted its 2014 Stock Option and Grant Plan (as amended, the “2014 Plan”), pursuant to which shares of the Company’s common stock were reserved for the issuance of stock options (incentive and non-statutory), restricted stock units (“RSUs”), and restricted stock to employees, directors, and consultants under terms and provisions established by the Company's board of directors and approved by the Company’s stockholders. The 2014 Plan was terminated in September 2021 in connection with the Direct Listing but continues to govern the terms of outstanding awards that were granted prior to the termination of the 2014 Plan. No further equity awards will be granted under the 2014 Plan. With the establishment of the 2021 Incentive Award Plan (the “2021 Plan”) as further discussed below, upon the expiration, forfeiture, cancellation, or reacquisition of any shares of Class A common stock underlying outstanding stock-based awards granted under the 2014 Plan, an equal number of shares of Class A common stock will become available for grant under the 2021 Plan. 2021 Incentive Award Plan In August 2021, the Company's board of directors adopted, and its stockholders approved, the 2021 Plan, which became effective in connection with the Direct Listing. The 2021 Plan provides for the grant of incentive stock options, nonqualified stock options, stock appreciation rights, restricted stock awards, RSU awards, performance bonus awards, performance stock units, dividend equivalent awards and other forms of equity compensation (collectively, “equity awards”). As of September 30, 2023 , a total of 18,268,935 shares of the Company's Class A common stock have been reserved for issuance under the 2021 Plan in addition to (i) any shares available for issuance under the 2014 Plan as of the effective date of the 2021 Plan, (ii) the number of shares represented by awards outstanding under the Company's 2014 Plan (“Prior Plan Awards”) that become available upon the expiration, forfeiture, cancellation, or reacquisition of any shares of Class A common stock underlying outstanding stock awards granted under the 2014 Plan, and (iii) an annual increase on the first day of each fiscal year beginning in 2022 and ending in 2031, equal to the lesser of (A) 5% of the shares of the Company's common stock outstanding (on an as-converted basis) on the last day of the immediately preceding fiscal year and (B) such smaller number of shares of stock as determined by the Company's board of directors; provided, however, that no more than 88,000,000 shares of stock may be issued upon the exercise of incentive stock options. Stock Option Awards Stock options granted under the 2014 Plan and the 2021 Plan (collectively, the “combined stock plans”) generally vest based on continued service over four years . Option activity under the Company's combined stock plans for the nine months ended September 30, 2023 is set forth below: Weighted Weighted average Aggregate Outstanding average remaining intrinsic stock exercise contractual value options price life (years) (in thousands) Balances as of December 31, 2022 16,767,752 $ 4.19 7.19 $ 132,298 Granted 425,352 11.94 Exercised ( 1,310,414 ) 2.72 Cancelled/forfeited ( 940,778 ) 7.03 Balances as of September 30, 2023 (1) 14,941,912 $ 4.36 6.53 $ 107,673 Exercisable as of September 30, 2023 (2) 12,693,443 $ 3.62 6.28 $ 100,956 (1) As no forfeitures are estimated due to the Company’s adoption of ASU No. 2016-09, all options are vested or expected to vest. As of September 30, 2023 , no options were outstanding that were subject to a future performance condition. (2) Exercisable shares include vested options as well as unvested shares that can be early exercised. The aggregate intrinsic values of options are calculated as the difference between the exercise price of the options and the market price for shares of the Company’s Class A common stock as of each period-end. The total intrinsic value of options exercised for the nine months ended September 30, 2023 and 2022 was $ 11.6 million and $ 28.4 million , respectively. Stock options granted during the nine months ended September 30, 2023 and 2022 had a weighted average grant date fair value of $ 6.69 per share and $ 8.27 per share, respectively. The fair value of options granted is being expensed over the vesting period of the options on a straight-line basis as the services are being provided. No tax benefits were realized from options during the periods. As of September 30, 2023, total unrecognized stock-based compensation expense related to options outstanding under the combined stock plans was $ 13.7 million . This unrecognized expense as of September 30, 2023 is expected to be recognized over the weighted average remaining vesting period of 2.38 years. As of September 30, 2023, the Company had 342,000 shares of non-employee stock options outstanding under the combined stock plans. The fair value of each option granted to employees under the 2021 Plan is estimated on the grant date using the Black-Scholes pricing model. Restricted Stock Units RSUs granted under the 2021 Plan generally vest based on continued service. RSUs granted pursuant to the 2014 Plan vest according to a service condition as well as a performance condition, through a liquidity event, including (i) a change in control of the Company or (ii) the initial public offering of the Company’s equity securities, following which the securities shall be publicly traded, which includes a direct listing. As a result of the Direct Listing, the performance condition for all RSUs granted pursuant to the 2014 Plan has been met. During the three and nine months ended September 30, 2023, the Company recorded $ 20.7 million and $ 55.9 million in stock-based compensation expense related to RSUs, respectively. During the three and nine months ended September 30, 2022, the Company recorded $ 13.5 million and $ 29.8 million in stock-based compensation expense related to RSUs, respectively. As of September 30, 2023, total unrecognized stock-based compensation expense related to RSUs was $ 161.3 million . This unrecognized expense as of September 30, 2023 is expected to be recognized over the weighted average remaining vesting period of 2.25 years. As of September 30, 2023, the Company had 176,205 shares of non-employee RSUs outstanding under the combined stock plans. RSU activity during the nine months ended September 30, 2023 was as follows: Restricted stock Weighted-average Balance as of December 31, 2022 9,914,125 $ 19.14 Granted 7,400,541 12.09 Vested ( 3,446,063 ) 17.66 Cancelled/forfeited ( 2,207,119 ) 18.40 Balance as of September 30, 2023 11,661,484 $ 15.24 2021 Employee Stock Purchase Plan In August 2021, the Company’s board of directors adopted, and its stockholders approved, the 2021 Employee Stock Purchase Plan (the “ESPP”), which became effective in connection with the Direct Listing. The ESPP authorizes the issuance of shares of Class A common stock pursuant to purchase rights granted to employees. As of September 30, 2023 , a total of 4,251,616 shares of the Company’s Class A common stock have been reserved for future issuance under the ESPP, in addition to any annual automatic evergreen increases in the number of shares of Class A common stock reserved for future issuance under the ESPP. The ESPP offers employees the option to purchase shares through a series of consecutive 12-month offering periods on each May 15th and November 15th (with two six-month purchase periods during each offering period). The price at which Class A common stock is purchased under the ESPP is equal to the lower of (i) 85 % of the closing trading price per share of the Company's Class A common stock on the first trading date of an offering period in which a participant is enrolled or (ii) 85 % of the closing trading price per share on the purchase date, which will occur on the last trading day of each purchase period, or such other price designated by the administrator. The initial offering period under the ESPP was longer than 12 months , commencing on September 28, 2021 and ending on November 14, 2022 . The first purchase period commenced on September 28, 2021 and ended on May 14, 2022. The ESPP offers a rollover feature pursuant to which, if the fair market value of a share of Class A common stock on the first purchase date is lower than the fair market value on the first trading day of the offering period, the respective offering period will terminate and each participant will be automatically enrolled in the offering period that commences immediately following the purchase date. In accordance with the rollover feature, immediately following the conclusion of each purchase period since the initial purchase period on May 14, 2022, the corresponding offering periods were terminated and participants were automatically enrolled in a new 12-month offering period. The impact of the rollover feature did not result in material incremental compensation cost for the nine months ended September 30, 2023. As of September 30, 2023, 0.7 million shares have been purchased under the ESPP. During the three and nine months ended September 30, 2023, the Company recognized $ 0.6 million and $ 1.9 million of stock-based compensation expense related to the ESPP, respectively. During the three and nine months ended September 30, 2022, the Company recognized $ 1.5 million and $ 4.5 million of stock-based compensation expense related to the ESPP, respectively. As of September 30, 2023, total unrecognized compensation cost related to the ESPP was $ 1.3 million , which will be amortized over a weighted average period of 0.49 years. Stock-based compensation expense, net of actual forfeitures is reflected in the condensed consolidated statements of operations and comprehensive loss (in thousands): Three Months Ended Nine Months Ended 2023 2022 2023 2022 Cost of revenue $ 1,947 $ 1,793 $ 5,426 $ 4,385 Research and development 9,285 7,486 27,173 19,153 Sales and marketing 7,843 5,029 21,677 11,474 General and administrative 4,010 4,184 9,876 11,819 Restructuring and other related charges — — 853 — Total stock-based compensation expense $ 23,085 $ 18,492 $ 65,005 $ 46,831 |