Share-Based Compensation | Share-Based Compensation The Company has issued incentive and non-qualifying stock options to employees and non-employee directors under the 2005 Stock Option/Restricted Stock Plan, the 2015 Equity Incentive Plan (the “2015 Plan”), and the 2018 Equity Incentive Plan (the “2018 Plan”). Employee stock options are granted with exercise prices at the fair value of the underlying common stock on the grant date, generally vest based on continuous employment over three The Company has also issued restricted stock units (“RSUs”) to employees and non-employee directors pursuant to the 2015 Plan and the 2018 Plan. Employee RSUs are measured based on the grant date fair value of the awards and generally vest based on continuous employment over three The Company has issued restricted stock awards (“RSAs”) to certain Brandfolder employees subject to vesting conditions. These shares were issued in a private placement transaction. As vesting of these RSAs is dependent on continuous employment, these were not considered part of the purchase price in accounting for the September 2020 acquisition. The RSAs are measured based on the grant date fair value of the awards and vest based on continuous employment over three years. The Company issued market-based performance share units (“PSUs”) to certain executives pursuant to the 2018 Plan during the year ended January 31, 2023. The target number of market-based PSUs granted was 251,027. The number of shares that can be earned range from 0% to 200% of the target number of shares, based on the relative growth of the Company’s total shareholder return as compared to the total shareholder return of the S&P Software and Services Select Index. These awards have two separate performance periods. The first tranche of awards has a one year performance period starting on the date of grant and ending on the first anniversary of the date of grant. The second tranche of awards has a two year performance period starting on the date of grant and ending on the second anniversary of the date of grant. These awards also include a service condition and vest on a graded vesting schedule, subject to continuous employment, over a three year period. The fair value of the PSUs granted was determined using a Monte Carlo simulation approach. Stock options The following table includes a summary of the option activity during the six months ended July 31, 2023: Options Outstanding Weighted-Average Exercise Price Outstanding at January 31, 2023 3,819,288 $ 23.42 Granted — — Exercised (145,724) 7.32 Forfeited or canceled (10,125) 67.00 Outstanding at July 31, 2023 3,663,439 23.94 Exercisable at July 31, 2023 3,031,579 17.76 Restricted stock units The following table includes a summary of the RSU activity during the six months ended July 31, 2023: Number of Shares Underlying Outstanding RSUs Weighted-Average Grant-Date Fair Value per RSU Outstanding at January 31, 2023 10,975,157 $ 46.56 Granted 836,732 45.09 Vested (2,193,483) 46.63 Forfeited or canceled (671,460) 47.08 Outstanding at July 31, 2023 8,946,946 46.37 Performance Share Units The following table includes a summary of the PSU activity during the six months ended July 31, 2023: Number of Shares Weighted-Average Grant-Date Fair Value per PSU Outstanding at January 31, 2023 251,027 $ 53.34 Granted — — Vested — — Forfeited or canceled — — Outstanding at July 31, 2023 251,027 53.34 Restricted stock awards The following table includes a summary of the RSA activity during the six months ended July 31, 2023: Number of Shares Weighted-Average Grant-Date Fair Value per Share Outstanding at January 31, 2023 19,895 $ 46.93 Granted — — Vested — — Forfeited or canceled — — Outstanding at July 31, 2023 19,895 46.93 2018 Employee Stock Purchase Plan In April 2018, we adopted our 2018 Employee Stock Purchase Plan (“ESPP”). The ESPP became effective on April 26, 2018, with the effective date of our initial public offering. Under our ESPP, eligible employees are able to acquire shares of Class A common stock by accumulating funds through payroll deductions of up to 15% of their compensation, subject to plan limitations. Purchases are accomplished through participation in discrete offering periods. Each offering period is six months (commencing each January 1 and July 1), with a purchase date following the end of the period, unless otherwise determined by our board of directors or our compensation committee. The purchase price for shares of our common stock purchased under our ESPP is 85% of the lesser of the fair market value of common stock on (i) the first trading day of the applicable offering period or (ii) the last trading day of the purchase period in the applicable offering period. Shares available for issuance The following table includes a summary of the Company’s shares available for issuance activity under our 2018 Plan and our ESPP during the six months ended July 31, 2023: 2018 Plan 2018 ESPP Balance at January 31, 2023 14,594,290 4,850,775 Authorized 6,592,251 1,318,450 Granted (836,732) (343,252) Forfeited or canceled 681,585 — Balance at July 31, 2023 21,031,394 5,825,973 The aggregate number of shares reserved for issuance under our ESPP will increase automatically on February 1 of each of the first 10 calendar years after the first offering date. The increase of shares is equal to 1% of the total outstanding shares of our Class A and Class B common stock as of the immediately preceding January 31 (rounded to the nearest whole share) or such lesser number of shares as may be determined by our board of directors. The aggregate number of shares issued over the term of our ESPP, subject to stock-splits, recapitalizations or similar events, may not exceed 20,400,000 shares of our Class A common stock. As of July 31, 2023, $2.4 million has been withheld on behalf of our employees for a future purchase under the ESPP and is recorded in accrued compensation and related benefits in the condensed consolidated balance sheets. Share-based compensation expense Share-based compensation expense included in the condensed consolidated statements of operations was as follows (in thousands): Three Months Ended July 31, Six Months Ended July 31, 2023 2022 2023 2022 Cost of subscription revenue $ 3,357 $ 2,849 $ 6,816 $ 5,460 Cost of professional services revenue 1,915 1,756 3,825 3,233 Research and development 17,611 15,974 35,043 31,589 Sales and marketing 18,989 16,707 38,043 31,452 General and administrative 10,151 8,202 20,075 17,654 Total share-based compensation expense $ 52,023 $ 45,488 $ 103,802 $ 89,388 We have excluded $1.4 million and $1.0 million of capitalized software development costs from share-based compensation expense in the three months ended July 31, 2023 and 2022, respectively, and $2.2 million and $1.7 million for the six months ended July 31, 2023 and 2022, respectively. |