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”). The Company has also issued restricted stock units (“RSUs”) to employees and non-employee directors pursuant to the 2015 Plan and the 2018 Plan. 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. Employee stock options are granted with exercise prices at the fair value of the underlying common stock on the grant date, in general vest based on continuous employment over four years, and expire 10 years from the date of grant. Employee RSUs are measured based on the grant date fair value of the awards and in general vest, based on continuous employment, over three Stock options The following table includes a summary of the option activity during the nine months ended October 31, 2022: Options Outstanding Weighted-Average Exercise Price Outstanding at January 31, 2022 4,573,482 $ 20.87 Granted 3,744 52.72 Exercised (659,022) 10.61 Forfeited or canceled (124,474) 44.99 Outstanding at October 31, 2022 3,793,730 21.89 Exercisable at October 31, 2022 3,113,378 13.03 Restricted stock units The following table includes a summary of the RSU activity during the nine months ended October 31, 2022: Number of Shares Underlying Outstanding RSUs Weighted-Average Grant-Date Fair Value per RSU Outstanding at January 31, 2022 7,281,232 $ 60.95 Granted 3,671,894 42.77 Vested (2,152,972) 56.36 Forfeited or canceled (1,213,914) 58.42 Outstanding at October 31, 2022 7,586,240 53.86 Restricted stock awards The following table includes a summary of the RSA activity during the nine months ended October 31, 2022: Number of Shares Weighted-Average Grant-Date Fair Value per Share Outstanding at January 31, 2022 56,288 $ 46.93 Granted — — Vested (28,144) 46.93 Forfeited or canceled (8,249) 46.93 Outstanding at October 31, 2022 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) and consists of one six-month purchase 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 activity during the nine months ended October 31, 2022 of the Company’s shares available for issuance under our 2018 Plan and our ESPP: 2018 Plan 2018 ESPP Balance at January 31, 2022 15,067,025 4,040,430 Authorized 6,390,477 1,278,096 Granted (3,675,638) (318,365) Forfeited or canceled 1,338,388 — Balance at October 31, 2022 19,120,252 5,000,161 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 under the ESPP by the number of shares equal to 1% of the total outstanding shares of our Class A common stock 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 in any particular year. 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 October 31, 2022, $3.4 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 October 31, Nine Months Ended October 31, 2022 2021 2022 2021 Cost of subscription revenue $ 2,517 $ 1,629 $ 7,977 $ 4,726 Cost of professional services revenue 1,436 1,034 4,669 2,648 Research and development 13,317 10,095 44,906 28,426 Sales and marketing 14,068 9,595 45,520 28,566 General and administrative 6,732 5,707 24,386 16,186 Total share-based compensation expense $ 38,070 $ 28,060 $ 127,458 $ 80,552 We have excluded $0.7 million and $0.5 million of capitalized software development costs from share-based compensation expense in the three months ended October 31, 2022 and 2021, respectively and $2.5 million and $1.5 million for the nine months ended October 31, 2022 and 2021, respectively. |