Stock-Based Compensation | 10. Stock-Based Compensation As of September 30, 2023 (unaudited) and December 31, 2022 , there were 500,000,000 shares of common stock authorized. As of September 30, 2023 (unaudited) and December 31, 2022, there were 144,696,156 and 142,917,080 shares of common stock issued and outstanding, respectively. Employee Equity Plans In April 2020, as part of the Take-Private Transaction, the board of managers of TopCo approved the Instructure Parent, LP Incentive Equity Plan (the “2020 Plan”) and the Instructure Co-Invest Agreement (the “Co-Invest Agreement”) to incentivize employees and to align the employees and management with the owners of the business. The 2020 Plan was terminated in July 2021 in connection with the initial public offering (the “IPO”). No further equity awards were granted under the 2020 Plan subsequent to the IPO. As of the IPO date, 2,271,698 vested incentive units under the 2020 Plan converted to 1,305,738 shares of the Company ’ s common stock and were released to the unit holders, and 6,126,802 unvested incentive units under the 2020 Plan were exchanged for 3,496,739 RSUs under the 2021 Plan. The RSUs will generally vest in 11 equal quarterly installments which commenced on September 1, 2021. In July 2021, our board of directors adopted the 2021 Omnibus Incentive Plan (the “2021 Plan”), which serves as the successor to the 2020 Plan. Accordingly, no shares remain available for issuance under the 2020 Plan. A total of 18,000,000 shares of the Company ’s common stock were initially reserved for issuance under the 2021 Plan. Pursuant to the terms of the 2021 Plan, the share reserve increased by 5,629,623 shares in January 2022 and 5,716,683 shares in January 2023. As of September 30, 2023, we had 19,827,266 shares of common stock available for future grants under the 2021 Plan. In July 2021, our board of directors adopted, and our stockholders approved the 2021 Employee Stock Purchase Plan (the “2021 ESPP”), which allows eligible employees to purchase shares of our common stock at a discount through payroll deductions of up to 15 % of their eligible compensation, subject to any plan limitations. The initial offering period ended on February 28, 2022. Each new offering period begins on or about March 1 and September 1 and is approximately six months in duration. On each purchase date, eligible employees will purchase our common stock at a price per share equal to 85 % of the lesser of (1) the fair market value of our common stock on the offering date or (2) the fair market value of our common stock on the purchase date. A total of 1,900,000 shares of the Company’s common stock were initially reserved for issuance under the 2021 ESPP. Pursuant to the terms of the 2021 ESPP, the share reserve increased by 1,407,406 shares in January 2022 and 1,429,171 shares in January 2023. As of September 30, 2023 (unaudited), 4,018,556 shares of common stock were available for purchase under the 2021 ESPP. During the unaudited three months ended September 30, 2023, we granted 153,795 RSUs to employees under the 2021 Plan. Each RSU entitles the recipient to receive one share of the Company ’s common stock upon vesting. The RSUs are subject to time-based service requirements and generally vest over a four-year service period. The grant date fair value of the RSUs granted during the unaudited three months ended September 30, 2023 was $ 28.00 , which represents the closing stock price for the underlying common stock on the grant date, with an aggregate fair value of $ 4.3 million. The following two tables present stock-based compensation by award type and where the stock-based compensation expense was recorded in our condensed consolidated statements of operations and comprehensive loss (in thousands): Three months ended Nine months ended 2023 2022 2023 2022 (unaudited) Options $ — $ — $ — $ 21 Restricted stock units 11,343 9,538 32,420 27,249 Shares issuable under employee stock purchase plan 412 522 1,201 1,653 Total stock-based compensation $ 11,755 $ 10,060 $ 33,621 $ 28,923 Three months ended Nine months ended 2023 2022 2023 2022 (unaudited) Subscription and support cost of revenue $ 459 $ 358 $ 1,312 $ 965 Professional services and other cost of revenue 603 451 1,639 1,292 Sales and marketing 3,145 2,813 9,142 8,162 Research and development 3,792 3,035 10,446 8,261 General and administrative 3,756 3,403 11,082 10,243 Total stock-based compensation $ 11,755 $ 10,060 $ 33,621 $ 28,923 In connection with the Take-Private Transaction on March 24, 2020, and except for certain executives, outstanding stock options and restricted stock units, and together with the stock options, “equity awards,” whether vested or unvested, were canceled and replaced with the right to receive $ 49.00 per share in cash, less the applicable exercise price per share and applicable withholding taxes (the “per share price”), with respect of each share of common stock underlying such award (“Cash Replacement Awards”). The per share price attributed to the unvested equity awards vests and is payable at the same time such equity awards would have vested pursuant to their original terms prior to the replacement. During the unaudited three and nine months ended September 30, 2023 the Company recognized $ 0.1 million and $ 0.6 million of stock-based compensation expense associated with Cash Replacement Awards, respectively, and $ 1.4 million and $ 4.3 million for the unaudited three and nine months ended September 30, 2022, respectively. Restricted Stock Units The following table summarizes the activity of RSUs for the unaudited nine months ended September 30, 2023 (in thousands, except per unit amounts): RSUs Weighted Average Grant Date Fair Value Per Unit Unvested and outstanding at December 31, 2022 3,437 $ 21.60 Granted 2,714 25.27 Vested ( 924 ) 22.32 Forfeited or canceled ( 570 ) 22.23 Unvested and outstanding at September 30, 2023 4,657 $ 23.53 As of September 30, 2023 (unaudited) and December 31, 2022, total unrecognized compensation cost related to unvested RSUs amounted to $ 100.0 million and $ 68.3 million, respectively, which is expected to be recognized over a weighted average period of 3.0 years and 3.1 years, respectively. The following table summarizes the activity of the incentive units granted under the 2020 Plan, subsequent to their conversion into RSUs under the 2021 Plan, for the unaudite d nine months ended September 30, 2023 (in thousands, except per unit amounts): RSUs Weighted Average Grant Date Fair Value Per Unit Unvested and outstanding at December 31, 2022 1,409 $ 10.72 Vested ( 750 ) 11.26 Forfeited or canceled ( 94 ) 11.08 Unvested and outstanding at September 30, 2023 565 $ 10.70 There were no incentive units granted subsequent to December 31, 2021. As of September 30, 2023 (unaudited) and December 31, 2022, we had $ 5.2 million and $ 14.2 million, respectively, of unrecognized stock-based compensation expense related to unvested incentive units exchanged for RSUs that are expected to be recognized over a weighted-average period of 0.6 and 1.3 years, respectively. 2021 ESPP The following table summarizes the assumptions relating to 2021 ESPP purchase rights used in a Black-Scholes option pricing model for the three months ended September 30, 2023 and 2022 (unaudited): Three months ended 2023 2022 Dividend yield None None Volatility 18 - 25 % 32 - 41 % Risk-free interest rate 5.20 - 5.47 % 0.6 - 3.34 % Expected life (years) 0.5 0.5 |