Stockholders' Equity | 10. Stockholders’ Equity and Stock-Based Compensation As of March 31, 2023 (unaudited) and December 31, 2022 , there were 500,000,000 shares of common stock authorized. As of March 31, 2023 (unaudited) and December 31, 2022, there were 143,478,526 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 provided for the grant of incentive stock options, profits interest, equity appreciation rights and other forms of awards to employees and non-employees granted or denominated in TopCo Units. Under the 2020 Plan, 10,000,000 Class B Units (“Incentive Units”) were reserved for issuance (“Incentive Carry”) and did not have a contractual life. Incentive Carry grants were subject to a service and a performance vesting condition based on the achievement of an EBITDA target as established by TopCo ’ s board of managers, over a performance period of four years. Additionally, TopCo granted 480,000 Incentive Units to certain members of the board of managers that were only subject to service-based vesting conditions over four years (“Board Carry”). These Incentive Units were not included in the Incentive Carry pool previously discussed and there was no contractual life. The Co-Invest Agreement offered employees the one-time opportunity to co-invest in TopCo by purchasing Units directly from TopCo for cash. Under the Co-Invest Agreement, the purchase price for one Class A unit and 72 Class B units was $ 1,000 , which is the same investment allocation between the two unit classes as the investment made by existing investors at the time of the Take-Private Transaction. The 2020 Plan was terminated in July 2021 in connection with 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 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 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 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 5,716,683 shares in January 2023. As of March 31, 2023, we had 19,627,649 shares of common stock available for future grant 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 1,429,171 shares in January 2023. As of March 31, 2023 (unaudited), 4,145,940 shares of common stock were available for purchase under the 2021 ESPP. During the three months ended March 31, 2023 (unaudited), we granted 2,539,452 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 values of the RSUs granted during the three months ended March 31, 2023 (unaudited) ranged from $ 24.24 to $ 26.41 , which represent the closing stock price for the underlying common stock on the respective grant dates, with an aggregate fair value of $ 63.7 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 2023 2022 (unaudited) Options $ — $ 19 Restricted stock units 9,599 8,863 Shares issuable under employee stock purchase plan 411 594 Total stock-based compensation $ 10,010 $ 9,476 Three months ended 2023 2022 (unaudited) Subscription and support cost of revenue $ 379 $ 282 Professional services and other cost of revenue 414 376 Sales and marketing 2,528 2,577 Research and development 3,174 2,540 General and administrative 3,515 3,701 Total stock-based compensation $ 10,010 $ 9,476 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 three months ended March 31, 2023 and 2022 (unaudited), the Company recognized $ 0.4 million and $ 1.7 million of stock-based compensation expense associated with the Cash Replacement Awards, respectively. Restricted Stock Units The following table summarizes the activity of RSUs for the unaudited three months ended March 31, 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 2,539 25.10 Vested ( 181 ) 21.54 Forfeited or canceled ( 250 ) 21.60 Unvested and outstanding at March 31, 2023 5,545 $ 23.20 As of March 31, 2023 (unaudited) and December 31, 2022, total unrecognized compensation cost related to unvested RSUs amounted to $ 120.0 million and $ 68.3 million, respectively, which is expected to be recognized over a weighted average period of 3.4 years and 3.1 years, respectively. The following table summarizes the activity of the Incentive Carry and Board Carry, subsequent to their conversion into RSUs under the 2021 Plan, for the unaudite d three months ended March 31, 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 ( 258 ) 10.74 Forfeited or canceled ( 40 ) 11.08 Unvested and outstanding at March 31, 2023 1,111 $ 10.75 There were no Incentive Units granted subsequent to December 31, 2021. As of March 31, 2023 (unaudited) and December 31, 2022, we had $ 11.0 million and $ 14.2 million 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 1.0 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 March 31, 2023 and 2022 (unaudited): Three months ended 2023 2022 Dividend yield None None Volatility 25 - 32 % 41 - 47 % Risk-free interest rate 3.34 - 5.20 0.06 Expected life (years) 0.5 0.5 - 0.6 |