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Q1 FY2027 Earnings Presentation October 20, 2026
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2 Safe Harbor This presentation and the investor call to which it relates contain certain forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995 that involve substantial risks and uncertainties. All statements other than statements of historical facts contained in this presentation are forward-looking statements, such as any statements that look to future events and include, among other things, our expectations regarding: mix of enrollment, revenue per enrollment, future financial and other trends, forecasts, assumptions and guidance, and future share repurchases. We have tried, whenever possible, to identify these forward-looking statements using words such as “outlook,” “forecasts,” “anticipates,” “trends,” “believes,” “estimates,” “continues,” “likely,” “may,” “opportunity,” “potential,” “projects,” “will,” “will be,” “expects,” “plans,” “intends,” “should,” “would” and similar expressions to identify forward-looking statements, whether in the negative or the affirmative. Such forward-looking statements involve known and unknown risks, uncertainties and other factors which could cause our actual results, performance or achievements to differ materially from those expressed in, or implied by, such statements. These risks, uncertainties, factors and contingencies include, but are not limited to: reduction of per pupil funding amounts at the schools we serve; inability to achieve a sufficient level of new enrollments to sustain our business model or to meet financial or operational guidance; limitations of the enrollment data we present, which may not fully capture trends in the performance of our business; failure to enter into new school contracts or renew existing contracts, in part or in their entirety; failure of the schools we serve, our vendors, or us to comply with our contracts, or federal, state and local laws and regulations, resulting in a loss of funding, an obligation to repay funds previously received, contractual remedies, or actions or proceedings against us; governmental investigations that could result in fines, penalties, settlements, or injunctive relief; declines or variations in academic performance outcomes of the students and schools we serve, including due to the evolution of curriculum standards, testing programs and state accountability metrics; harm to our reputation resulting from poor performance or misconduct by operators or us in any school in our industry and/or in any school which we operate; legal and regulatory challenges from opponents of virtual public education or for-profit education companies; potential violation of laws and regulations relating to privacy and data protection, including such laws and regulations as may apply to children’s data; changes in national and local economic and business conditions and other factors, such as natural disasters, pandemics and outbreaks of contagious diseases and other adverse public health developments; discrepancies in interpretation of legislation by regulatory agencies that may lead to payment or funding disputes; termination of our contracts, or a reduction or termination in the scope of services, with schools; failure to develop the Career Learning business; entry of new competitors with superior technologies (including artificial intelligence) and lower prices; unsuccessful integration of mergers, acquisitions and joint ventures; failure to further develop, maintain and enhance our technology, products, services and brands; inadequate recruiting, training and retention of effective teachers and employees; infringement of our intellectual property; disruptions to our Internet-based learning and delivery systems, including, but not limited to, our data storage systems and third-party cloud infrastructure, systems and facilities, including as a result of cybersecurity attacks; misuse or unauthorized disclosure of student and personal data; failure to prevent or mitigate a cybersecurity incident that affects our systems or our data; problems in the implementation of new information technology systems and technology; failure by us or third parties to maintain and support information technology systems, including addressing quality issues and timely delivering new products and enhancements; risks related to the use, implementation and regulation of AI and other emerging technologies, including in the education of children, and their use by third-party vendors; risks related to our stock repurchase program; the extent to which we acquire businesses or change our capital allocation strategy or the implementation thereof; changes in our effective tax rate and additional liabilities; and other risks and uncertainties associated with our business described in the risk factors discussed in the Company’s Annual Report on Form 10-K for the year ended June 30, 2026 and any subsequently filed Quarterly Reports on Form 10-Q or the Company’s other filings with the Securities and Exchange Commission. Although the Company believes the expectations reflected in such forward-looking statements are based upon reasonable assumptions, it can give no assurance that the expectations will be attained or that any deviation will not be material. All information in this presentation is as of today’s date, and the Company undertakes no obligation to update any forward- looking statement to conform the statement to actual results or changes in the Company’s expectations, except where we are expressly required to do so by law.
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Disruptor in Education Innovator with the scale, expertise & long-term customer relationships to change education Sustainable & Growing Virtual School Business Accelerating secular shift toward virtual education and school choice New Products & Technologies Leveraging capabilities and assets to address market failures or shortcomings Experienced Leadership Team Deep educational, regulatory, and policy expertise Financial Track Record Track record of revenue and profitability growth with a strong balance sheet to support organic and inorganic growth 3 Compelling Long-Term Investment Thesis
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4 Q1 FY2027 Performance Demand for educational choices remains strong • Parent satisfaction with traditional K-12 schools hits new low Clearer focus and accountability across the business • Alignment of resources with our highest priorities Note: To supplement our financial statements presented in accordance with U.S. generally accepted accounting principles (GAAP), we also present non-GAAP financial measures including adjusted operating income, adjusted EBITDA, and adjusted earnings per share. Management believes that these additional metrics provide useful information to investors relating to our financial performance. A reconciliation of these non-GAAP financial measures to the most directly comparable GAAP financial measures is provided in the Appendix to this presentation. Q1 FY2027 Highlights Adjusted Operating Income $78.6M, -3.1% YoY Adjusted EBITDA $111.8M, +3.1% YoY Adjusted EPS $1.37, -9.9% YoY Turning opportunity into results • Improved outcomes and customer experience; a more focused path to long-term growth Committed to achieving FY2028 targets • Continued progress against FY2028 targets outlined in our November 2023 Investor Day Revenue $639.4M, +3.0% YoY
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5 Increasing demand for virtual education options Secular trends driving demand Top reasons parents enroll students in virtual education Health & wellbeing concerns • Bullying • Negative social experience • Behavioral / social issues • School safety Value flexibility and individualized pace • Mobile / military family • Seeking 1:1 instruction • Academically lagging • Working student • Athletics Concern about environment at previous school • Academic struggles • Disciplinary needs • Special needs • Religion Percentage of parents who considered, searched for, or enrolled a child in a new school in 2025; 15% of which enrolled in a full-time online school Percentage of parents who fear for the safety of their children at school Percentage of K-12 parents who support making K-12 education more flexible, including the schools they can attend 75% 44% 81% Percentage of Americans who are satisfied with K-12 education in the U.S. 32%
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6 Revenue ($M) Adjusted Operating Income ($M) Key Financial Metrics Strong business model and competitive position Demonstrated track record of profitability Continued demand for school options $58 $136 $142 $131 $81 $159 $140 $118 $79 $135 $- $20 $40 $60 $80 $100 $120 $140 $160 $180 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Guidance FY25 FY26 FY27 $551 $587 $613 $654 $621 $631 $630 $636 $639 $625 $- $100 $200 $300 $400 $500 $600 $700 $800 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Guidance FY25 FY26 FY27 $645 $145 1. Guidance as of October 20, 2026 11
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7 Revenue and Enrollment Trends 1Q27 YoY enrollment growth (2.5)% Enrollment Trends General Education average enrollments decreased 8.5K, down 6.2% YoY Career Learning average enrollments increased 2.2K, up ~2.0% YoY Three months ended September 30, 2026 2025 Change Revenue ($M) General Education $356.6 $363.1 (1.8)% ↓ Career Learning Middle – High School 272.1 241.5 12.7% ↑ Adult 10.7 16.3 (34.4)% ↓ Total Career Learning 282.8 257.8 9.7% ↑ Total $639.4 $620.9 3.0% ↑ Enrollments (K) General Education, K-12 129.2 137.7 (6.2)% ↓ Career Learning, Middle – High School 112.2 110.0 2.0% ↑ Total 241.4 247.7 (2.5)% ↓
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Guidance mid-points • FY27 Revenue: +2% YoY – Midpoint of guidance • FY27 AOI: +3% YoY – Midpoint of guidance 8 FY27 Guidance Balances Growth with Investment Execution 1. Guidance as of October 20, 2026 Q2 FY 27 Guidance1 FY27 Guidance1 ($, M) Low High Low High Revenue $625M $645M $2.530B $2.610B Adjusted Operating Income $135M $145M $500M $530M Capital Expenditures $19M $21M $70M $80M Effective Tax Rate 24% 26% Guidance reflects actions underway to improve execution and strengthen the business
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9 Strong Balance Sheet with Low Debt Cash position, low leverage ratio, and consistent cash flows provide options for capital allocation Leverage ratio1 of 0.10x 1. Leverage ratio is a non-GAAP measure defined as Net Debt (total debt obligations of $608.6M less cash and cash equivalents of $547.8M) divided by Adjusted EBITDA of $621.0M for the twelve months ended September 30, 2026 September 30, 2026 Select balance sheet and other information ($M) Cash, Cash Equivalents & Marketable Securities $884.2 Accounts Receivable, Net 854.8 Accounts Payable 75.9 Total Debt Obligations $608.6
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10 Disciplined Capital Allocation Prioritizing organic growth, new product and technology development, and synergistic M&A Organic Growth • Invest in academic quality and student / customer experience supporting outcomes / retention • Technology advancements to improve personalization and outcomes • Implement innovative products across portfolio Strategic Acquisitions • Leverage platform across verticals • High-growth, high-margin targets providing synergies Capital Return • Evaluate approaches to return cash to stockholders over the long term • $500M share repurchase program authorization extended through October 31, 2027; ~$311M remaining under current authorization
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Compelling Long-Term Growth Targets 11 Continued progress against FY2028 targets Total Revenue ($B) $415M $201M $294M $466M $498M $585M $0M $200M $400M $600M $800M FY2023 FY2024 FY2025 FY2026 FY2028 Target $2.70B $1.84B $2.04B $2.41B $2.52B $3.30B $0.00B $0.50B $1.00B $1.50B $2.00B $2.50B $3.00B $3.50B FY2023 FY2024 FY2025 FY2026 FY2028 Target 10% CAGR to mid-point (FY23-28) 20% CAGR to mid-point (FY23-28) Adj. Operating Income ($M) Diluted EPS ($) $6.15 $2.97 $4.69 $5.95 $7.14 $8.35 $- $1.00 $2.00 $3.00 $4.00 $5.00 $6.00 $7.00 $8.00 $9.00 FY2023 FY2024 FY2025 FY2026 FY2028 Target 20% CAGR to mid-point (FY23-28) Depicts low-high range for FY2028 targets
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Board has authorized $500M in share buybacks through October 2027 12 Completed ~$189M as of 9/30/2026 $500M $311M Buyback authorization as of 11/3/2025 Completed as of 9/30/2026 Remaining authorization $0M $100M $200M $300M $400M $500M $600M $189M
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Appendix 13
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Reconciliation of Net Income to EBITDA and Adjusted EBITDA 14 Three months ended September 30, LTM ended September 30, ($, M) 2026 2025 2026 Net income $64.9 $68.8 $334.3 Interest expense, net 2.9 3.1 11.6 Other income, net (1.4) (16.9) 13.2 Income tax expense 17.8 14.4 106.2 (Income) loss from equity method investments 0.1 (0.4) 0.7 Depreciation and amortization 34.9 29.2 132.3 EBITDA 119.2 98.2 598.3 Stock-based compensation expense (7.4) 10.2 22.7 Adjusted EBITDA $111.8 $108.4 $621.0
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15 Reconciliation of Income from Operations to Adjusted Operating Income Three months ended September 30, ($, M) 2026 2025 Income from operations $84.3 $69.0 Amortization of intangible assets 1.7 1.9 Stock-based compensation expense (7.4) 10.2 Adjusted operating income $78.6 $81.1
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16 Reconciliation of Income from Operations to Adjusted Operating Income Year ended June 30, ($, M) 2023 2024 2025 2026 Income from operations $165.5 $249.6 $360.1 $450.8 Amortization of intangible assets 15.2 12.9 9.9 7.3 Stock-based compensation expense 20.3 31.4 36.7 40.3 Impairment of long-lived assets - - 59.5 - Adjusted operating income $201.0 $293.9 $466.2 $498.4
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17 Reconciliation of Income from Operations to Adjusted Operating Income Three months ended ($, M) Sept. 30, 2024 Dec. 31, 2024 March 31, 2025 June 30, 2025 Sept. 30, 2025 Dec. 31, 2025 March 31, 2026 June 30, 2026 Income from operations $47.3 $125.1 $130.8 $56.9 $69.0 $146.9 $129.1 $105.9 Amortization of intangible assets 2.7 2.6 2.3 2.4 1.9 1.8 1.7 1.7 Stock-based compensation expense 8.4 7.9 8.6 11.8 10.2 10.3 9.6 10.2 Impairment of long-lived assets - - - 59.5 - - - - Adjusted operating income $58.4 $135.6 $141.7 $130.6 $81.1 $159.0 $140.4 $117.8
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Three months ended September 30, ($, M) 2026 2025 Net income attributable to common stockholders $64.9 $ 68.8 Amortization of intangible assets 1.7 1.9 Stock-based compensation expense (7.4) 10.2 Income tax effect on adjustments above (2.0) (8.9) Adjusted net income attributable to common stockholders $ 57.2 $ 72.0 Share computation: Weighted average common shares — diluted 44,828,092 49,222,851 Effect of capped call transactions (2,958,006) (1,803,506) Adjusted weighted average common shares — diluted 41,870,086 47,419,345 Adjusted earnings per share $ 1.37 $ 1.52 18 Reconciliation of Net Income to Adjusted Earnings Per Share
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Three months ended September 30, ($, per share) 2026 2025 Diluted net income per share $ 1.45 $ 1.40 Amortization of intangible assets 0.04 0.04 Stock-based compensation expense (0.16) 0.20 Income tax effect on adjustments above (0.05) (0.18) Effect of capped call transactions 0.09 0.06 Adjusted earnings per share $ 1.37 $ 1.52 19 Reconciliation of Diluted Net Income Per Share to Adjusted Earnings Per Share
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Three months ended September 30, ($, M) 2026 2025 Net cash used in operating activities $ (124.8) $ (195.8) Purchases of property and equipment - (0.3) Capitalized software development costs (17.9) (13.7) Capitalized curriculum development costs (6.6) (7.7) Free Cash Flow $ (149.3) $ (217.5) Reconciliation of Net Cash used in Operating Activities to Free Cash Flow 20
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Reconciliation of Income from Operations to Adjusted Operating Income 21 Three Months Ended December 31, 2026 Year Ended June 30, 2027 ($, M) Low High Low High Income from operations $ 126.0 $ 134.5 $ 479.5 $ 503.5 Stock-based compensation expense 7.5 8.5 15.0 19.0 Amortization of intangible assets 1.5 2.0 5.5 7.5 Adjusted operating income $ 135.0 $ 145.0 $ 500.0 $ 530.0
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22 Effect of Convertible Notes on Share Dilution Convertible Senior Notes (Illustrative Dilution Example) • Stride Convertible Notes: $420M principal (7.9M shares underlying); Maturity date 9/1/2027 • Irrevocably elected that all future conversions of the notes will be settled pursuant to combination settlement, generally requiring the principal amount to be settled in cash • Any excess of the conversion value over the principal amount can be settled, at Stride’s election, in cash or shares of our common stock • Incremental shares are reported for GAAP purposes but are not issued at the time of reporting • Stride’s capped call transactions completed at the time of the issuance of the convertible notes effectively raise the potential dilution point of the convertible notes from $52.88 to $86.17 • Below are some examples of potential dilution from the Notes at various share prices: 1. Non-GAAP Dilution is equal to the number of shares owed for settlement of the Convertible Notes less the shares expected to be received by Stride for the capped call transaction 2. Q1 FY2027 average stock price LRN Illustrative Avg. Quarterly Stock Price Shares owed on Convertible Notes Shares received from capped call transactions GAAP Dilution Non-GAAP Dilution1 $70 1,942,578 1,942,578 1,942,578 - $75 2,342,578 2,342,578 2,342,578 - $84.262 2,958,006 2,958,006 2,958,006 - $85 3,001,402 3,001,402 3,001,402 - $90 3,275,911 2,937,911 2,937,911 338,001 $95 3,521,525 2,783,284 2,783,284 738,242 $100 3,742,578 2,644,119 2,644,119 1,098,459 $105 3,942,578 2,518,209 2,518,209 1,424,369 $110 4,124,396 2,403,745 2,403,745 1,720,651 $115 4,290,404 2,299,234 2,299,234 1,991,170