For more than 25 years, Stride, Inc. (the “Company,” “we” or “our”) has been a national leader in online education and educational technology. We have unmatched innovation, scale, expertise, and relationships with school districts, public charter schools, and educational institutions throughout the United States. Indeed, our foundation for success is strong, and our opportunities for growth are many, particularly given the nationwide demand for alternative education solutions. Fiscal year 2026 performance spotlights our success and competitive differentiators. For example, we:

Over the past few months, we have also made important changes to the Company’s Board of Directors (the “Board”), leadership, and governance to position the Company for its next chapter of profitable growth and enhance stockholder value.

We have a long record of evolving our Board and our leadership team to reflect the needs of the Company and our strategic direction. In connection with Mr. Haggart’s appointment, Allison Lawrence temporarily resigned from the Board and the Compensation Committee effective October 22, 2026 and is serving as a non-voting Board observer. Immediately after this year’s Annual Meeting of Stockholders, which will be held on December 10, 2026 (the “Annual Meeting”), we will welcome Dr. Steven Guttentag to join the Board and welcome Ms. Lawrence back to our Board, and our Board size will be increased from eight to 10. With the new members joining the Board, existing Board expertise will be further strengthened and complemented, particularly with additional experience in technology-based education, emerging technologies, capital allocation, capital markets and marketing.

Our work to ensure we fully realize the Company’s upside growth and value creation potential is continuing. We are focused on ensuring that the right priorities, initiatives, and organizational structure are in place to best position the Company for profitable growth and to deliver on its mission of helping learners of all ages reach their potential through inspired teaching and personalized learning. We look forward to engaging with stockholders about these initiatives, the Company’s performance and progress, and the matters to be considered at the Annual Meeting, as detailed in the enclosed proxy materials.

IT IS IMPORTANT THAT YOUR SHARES BE REPRESENTED AT THE ANNUAL MEETING REGARDLESS OF THE NUMBER OF SHARES YOU OWN OR WHETHER OR NOT YOU ARE ABLE TO ATTEND THE ANNUAL MEETING IN PERSON.

Whether or not you plan to attend the Annual Meeting, we urge you to vote promptly on the matters described in the Proxy Statement. Please vote electronically via the Internet or by telephone, if permitted by the broker, bank or other nominee that holds your shares, or if you receive a paper copy of the proxy materials, please complete, sign, date and return the accompanying proxy card or voting instruction form. Voting electronically, by telephone or by returning your proxy card or voting instruction form in advance of the Annual Meeting does not deprive you of your right to attend the Annual Meeting. Thank you for being a stockholder and for your continued support of the Company.

The annual meeting of stockholders of Stride, Inc., a Delaware corporation (“Company”), will be held at the law firm of Latham & Watkins LLP, 555 Eleventh Street, NW, Suite 1000, Washington, DC 20004-1304, on Thursday, December 10, 2026, at 11:00 a.m., Eastern Time (“Annual Meeting”).

At the Annual Meeting, stockholders will be asked to:

Stockholders of record at the close of business on October 19, 2026, the record date, will receive notice of and be allowed to vote at the Annual Meeting. The foregoing matters are described in more detail in the Proxy Statement. In addition, financial and other information about the Company is contained in the Annual Report to Stockholders for the fiscal year ended June 30, 2026 (“Annual Report”), which includes our Annual Report on Form 10-K for the fiscal year ended June 30, 2026 (“fiscal 2026”), as filed with the U.S. Securities and Exchange Commission (“SEC”) on August 4, 2026.

We have elected to distribute our proxy materials primarily over the Internet rather than mailing paper copies of those materials to each stockholder, which will decrease our printing and distribution costs and allow for convenient access to and delivery of materials in an easily searchable format. If you would prefer to receive paper copies of our proxy materials, please follow the instructions included in the Notice of Internet Availability of Proxy Materials that was mailed to our stockholders on or about October 27, 2026.

For admission to the Annual Meeting, stockholders should come to the stockholder check-in table. Those who hold shares of our common stock in their own names should provide identification and have their ownership verified against the list of registered stockholders as of the close of business on the record date, October 19, 2026. Those who have beneficial ownership of stock through a broker, bank or other nominee must bring account statements or letters from the broker, bank or other nominee indicating that they owned our common stock as of the close of business on the record date, October 19, 2026. To vote at the meeting, those who have beneficial ownership of stock through a broker, bank or other nominee must bring a legal proxy, which can be obtained only from the broker, bank or other nominee.

A list of stockholders entitled to vote at the Annual Meeting will be available for inspection by any stockholder for any purpose germane to the Annual Meeting, during regular business hours, for a period of 10 days ending on the day before the Annual Meeting, at the Company’s principal place of business at 11720 Plaza America Drive, 9th Floor, Reston, VA 20190.

Your vote is important to us. We encourage you to read the Proxy Statement and promptly submit your proxy or voting instructions by Internet, telephone, or mail. Voting before the Annual Meeting will not prevent you from voting your shares at the Annual Meeting, if you desire to do so.

This Proxy Statement is provided in connection with the solicitation of proxies by and on behalf of the Board of Directors (the “Board”) of Stride, Inc., a Delaware corporation, for use at the annual meeting of stockholders to be held at the law firm of Latham & Watkins LLP, 555 Eleventh Street, NW, Suite 1000, Washington, DC 20004-1304, on Thursday, December 10, 2026, at 11:00 a.m., Eastern Time, and any adjournments or postponements thereof (the “Annual Meeting”). “Stride,” “we,” “our,” “us” and the “Company” each refer to Stride, Inc. The mailing address of our principal executive offices is 11720 Plaza America Drive, 9th Floor, Reston, VA 20190. This Proxy Statement will be made available on or about October 27, 2026 to holders of record as of the close of business on October 19, 2026 of our common stock, par value $0.0001 per share (“Common Stock”).

We are providing access to our proxy materials primarily over the Internet rather than mailing paper copies of those materials to each stockholder. On or about October 27, 2026, we will mail a Notice of Internet Availability of Proxy Materials (the “Notice”) to all stockholders entitled to vote at the Annual Meeting, except for those stockholders who received paper copies of the proxy materials. The Notice tells you how to:

Our Board has fixed the close of business on October 19, 2026 as the record date (“Record Date”) for determining the stockholders entitled to notice of, and to vote at, the Annual Meeting. On the Record Date, we had 42,048,853 shares of Common Stock outstanding and entitled to vote.

Holders of record of Common Stock on the Record Date will be entitled to one vote per share on any matter that may properly come before the Annual Meeting and any adjournments or postponements of the Annual Meeting.

A majority of the shares of Common Stock issued and outstanding and entitled to vote at the Annual Meeting, the holders of which are present in person or represented by proxy, will constitute a quorum for the transaction of business at the Annual Meeting. If a quorum is not present at the Annual Meeting, we expect that the Annual Meeting will be adjourned or postponed in order to solicit additional proxies.

If a quorum is present, (i) a plurality of votes present in person or represented by proxy at the Annual Meeting and entitled to vote on the election of directors is required to elect the members of the Board; (ii) the affirmative vote of the holders of a majority in voting power held by the stockholders present in person or represented by proxy at the Annual Meeting is required for (A) the ratification of the appointment of KPMG LLP (“KPMG”) as the Company’s independent registered public accounting firm for the fiscal year ending June 30, 2027 (“fiscal 2027”) and (B) the non-binding advisory resolution approving the compensation of the named executive officers (“NEOs”) of the Company.

Broker non-votes occur when a nominee holding shares of voting securities for a beneficial owner does not vote on a particular proposal because the nominee does not have discretionary voting power on that proposal and has not received instructions from the beneficial owner. Under the rules that govern brokers who have record ownership of shares that are held in “street name” for their clients, brokers may vote such shares on behalf of their clients with respect to “routine” matters (such as the ratification of auditors in Proposal 2), but not with respect to non-routine matters (such as Proposals 1 and 3).

Abstentions and withheld votes, and broker non-votes, if any, are included in determining whether a quorum is present. Withheld votes and broker non-votes, if any, do not affect the voting results with respect to the election of directors. However, because abstentions are considered present in person or represented by proxy, abstentions will have the effect of a vote against the approval of Proposals 2 and 3, which require the affirmative vote of the holders of a majority in voting power held by the stockholders present in person or represented by proxy at the Annual Meeting. Likewise, if any broker non-votes are present at the meeting, then any such broker non-votes would have the effect of a vote against Proposals 2 and 3.

Your vote is important. Whether or not you plan to attend the Annual Meeting, please promptly submit your proxy or voting instructions by Internet, telephone, or mail. For specific instructions on how to vote your shares, please refer to the instructions found on the Notice of Internet Availability of Proxy Materials you received in the mail or, if you received a paper copy of the proxy materials, the enclosed proxy card. If you are a beneficial owner of shares registered in the name of your broker, bank or other nominee, you should have received voting instructions with these proxy materials from that organization rather than from us. Simply vote using one of the methods provided by your broker, bank or other nominee to ensure that your vote is counted.

If you are a stockholder of record as of the close of business on the Record Date, you may attend the Annual Meeting and vote your shares of Common Stock in person instead of voting by Internet or telephone or returning your signed proxy card (if you request a paper copy). However, we urge you to vote in advance even if you are planning to attend the Annual Meeting. If you are a beneficial owner of shares of Common Stock registered in the name of your broker, bank or other nominee, you must obtain a valid proxy from your broker, bank or other nominee to vote your shares of Common Stock in person at the Annual Meeting.

Shares of our Common Stock represented at the Annual Meeting by properly executed proxies received prior to or at the Annual Meeting, and not revoked prior to or at the Annual Meeting, will be voted at the Annual Meeting, and at any adjournments, continuations or postponements of the Annual Meeting, in accordance with the instructions on the proxy cards.

If a proxy is duly executed and submitted without instructions, the shares of Common Stock represented by that proxy will be voted:

FOR the election of each of the Board nominees named in Proposal 1;

FOR Proposal 2, the ratification of the appointment of KPMG as the Company’s independent registered public accounting firm for fiscal 2027;

FOR Proposal 3, the approval, on a non-binding advisory basis, of the compensation of the NEOs of the Company; and

In the discretion of the proxy holders regarding any other matters properly presented for a vote at the Annual Meeting or any adjournments or postponements of the Annual Meeting.

A record holder who executes a proxy may revoke it before or at the Annual Meeting by: (i) delivering to our corporate secretary a written notice of revocation of a previously delivered proxy, with such notice dated after the previously delivered proxy; (ii) duly executing, dating and delivering to our corporate secretary a subsequent proxy card; (iii) voting again by telephone; (iv) voting again via the Internet; or (v) attending the Annual Meeting and voting in person. Attendance at the Annual Meeting will not, in and of itself, constitute revocation of a proxy. Any written notice revoking a proxy should be delivered to Stride, Inc., Attn: General Counsel and Secretary, 11720 Plaza America Drive, 9th Floor, Reston, VA 20190. If your shares of Common Stock are registered in the name of your broker, bank or other nominee, you must follow the instructions of such broker, bank or other nominee to revoke a proxy.

The Annual Meeting will be held on December 10, 2026 at 11:00 a.m., Eastern Time, at the law firm of Latham & Watkins LLP, 555 Eleventh Street, NW, Suite 1000, Washington, DC 20004-1304. For admission to the Annual Meeting, stockholders should come to the stockholder check-in table. Those who hold shares of Common Stock in their own names should provide identification and have their ownership verified against the list of registered stockholders as of the close of business on the Record Date. Those who have beneficial ownership of stock through a broker, bank or other nominee must bring account statements or letters from the broker, bank or other nominee indicating that they owned Common Stock as of the close of business on the Record Date.

Rules of conduct regarding the Annual Meeting will be provided during the Annual Meeting. To vote at the Annual Meeting, those who have beneficial ownership of Common Stock through a broker, bank or other nominee must bring a legal proxy, which can be obtained only from the broker, bank or other nominee.

We are soliciting proxies for the Annual Meeting from our stockholders, and we will bear the entire cost of soliciting proxies from our stockholders. Copies of solicitation materials will be furnished to brokerage houses, fiduciaries and custodians holding Common Stock for the benefit of others, so that such brokerage houses, fiduciaries and custodians may forward the solicitation materials to such beneficial owners. We may reimburse persons representing beneficial owners of Common Stock for their expenses in forwarding solicitation materials to those beneficial owners. Original solicitation of proxies by mail may be supplemented by telephone or personal solicitation by our directors, officers or other regular employees of the Company. No additional compensation will be paid to our directors, officers or other regular employees for these services.

The Company has retained Innisfree M&A Incorporated (“Innisfree”) to assist in obtaining proxies from stockholders for the Annual Meeting. The estimated cost of such services is $25,000, plus out-of-pocket expenses. Innisfree may be contacted at (877) 750-8129.

We do not expect that any matter other than the proposals presented in this Proxy Statement will be brought before the Annual Meeting. However, if other matters are properly presented at the Annual Meeting or any adjournments or postponements of the Annual Meeting, then the proxy holders will vote in their discretion with respect to those matters.

If a quorum is not present at the Annual Meeting, the Annual Meeting may be adjourned from time to time upon the approval of the holders of shares of Common Stock representing a majority of the voting stock represented in person or by proxy at the Annual Meeting, until a quorum is present or represented. Any business may be transacted at the adjourned meeting (at which a quorum shall be present or represented) which might have been transacted at the meeting originally noticed. If the adjournment is for more than 30 days, or if after the adjournment a new record date is fixed for the adjourned meeting, a notice of the adjourned meeting shall be given to each stockholder of record entitled to vote at the meeting. We do not currently intend to seek an adjournment of the Annual Meeting.

The Board currently consists of eight members, each of whose terms expire at the Annual Meeting. Each of our eight current directors has been nominated for election for a term expiring at the 2027 annual meeting of stockholders (the “2027 Annual Meeting”). The eight nominees for election at the Annual Meeting are: Aida M. Alvarez, Steven B. Fink, Dylan G. Haggart, Robert E. Knowling, Jr., Liza McFadden, Brian A. Shepherd, Ralph Smith and Joseph A. Verbrugge. Each of the nominees has agreed to serve as a director if elected, and the Company believes that each nominee will be available to serve.

As previously disclosed in the Company’s Current Report on Form 8-K filed on October 9, 2026, pursuant to a Cooperation Agreement, dated October 8, 2026 (the “Cooperation Agreement”), by and among the Company and Fivespan Partners, LP (“Fivespan”), Fivespan Partners Fund, Ltd, Fivespan Partners GP, LLC and Dylan G. Haggart (collectively with Fivespan, Fivespan Partners Fund, Ltd and Fivespan Partners GP, LLC, the “Investor Group”), the Board appointed Mr. Haggart to serve as a director on the Board, effective as of October 22, 2026, with an initial term expiring at the Annual Meeting. On October 8, 2026, Ms. Lawrence tendered her resignation from the Board and the Compensation Committee, effective immediately prior to Mr. Haggart’s appointment, to create a vacancy for Mr. Haggart. Since his appointment, Mr. Haggart has served as Co-Chair of the Capital Allocation Committee and as a member of the Compensation Committee.

The Board will increase its size from eight to 10 directors effective immediately following the conclusion of the Annual Meeting. At that time, the Board will appoint Dr. Steven Guttentag and re-appoint Ms. Lawrence to serve as directors, each for a term expiring at the 2027 Annual Meeting and until his or her successor is elected and qualified, or until his or her earlier resignation, death or removal. Following these appointments, nine of the Board’s 10 directors will be “independent” as defined in the currently applicable listing standards of the New York Stock Exchange (“NYSE”) and the rules and regulations of the SEC. Upon Dr. Guttentag’s appointment to the Board, he will join the Academic Committee and the Nominating and Corporate Governance Committee. Upon Ms. Lawrence’s re-appointment to the Board, she will rejoin the Compensation Committee. Dr. Guttentag and Ms. Lawrence are not nominees, and stockholders are not being asked to vote on their election at the Annual Meeting.

Pursuant to the Cooperation Agreement, Dr. Guttentag has served as a non-voting observer to the Board since October 8, 2026, and Ms. Lawrence has served as a non-voting observer to the Board since October 22, 2026. Both will continue to serve as non-voting observers until their respective appointments to the Board immediately following the conclusion of the Annual Meeting.

Other than the Cooperation Agreement, there is no other arrangement or understanding between Mr. Haggart or Dr. Guttentag on the one hand, and any other persons on the other hand, pursuant to which Mr. Haggart or Dr. Guttentag was appointed as a director or a board observer of the Company.

The following table shows the composition of age, tenure, gender and racial or ethnic backgrounds of our director nominees, and Dr. Guttentag and Ms. Lawrence, who will be appointed or re-appointed, as applicable, to the Board immediately following the conclusion of the Annual Meeting. Data reflected for gender and racial or ethnic backgrounds are based on voluntary reporting. The Board believes that this balance in age and tenure and wide range of backgrounds and experience will provide broad and valuable perspectives to the Board that will lead to a well-functioning Board. The Board statistics shown below are measured immediately following the conclusion of the Annual Meeting.

The names and ages of the nominees, their principal occupations and employment during the past five years, and other information regarding them are as follows.

Set forth below is biographical information for each of our current executive officers who is not also a director.

Our Board met eight times in person or telephonically during fiscal 2026. Each director serving on the Board in fiscal 2026 attended at least 75% of the total Board and committee meetings to which they were assigned during such director’s term of service. Our policy with respect to director attendance at the annual meeting of stockholders is to encourage, but not require, director attendance. Mr. Rhyu was the only then-serving member of our Board to attend our 2025 annual meeting of stockholders. Our director attendance policy is included in our Corporate Governance Guidelines, which are available on our website at https://investors.stridelearning.com/governance.

Our Board has affirmatively determined that, other than Mr. Knowling, who is not independent because he is the CEO of the Company, each of the seven other director nominees is “independent” as defined in the currently applicable listing standards of the NYSE and the rules and regulations of the SEC. In addition, Ms. Lawrence, who served as a director during fiscal 2026 and has temporarily resigned from the Board and is serving as a non-voting Board observer, is “independent” as defined in the currently applicable listing standards of the NYSE and the rules and regulations of the SEC. Effective as of immediately following the conclusion of the Annual Meeting, the Board will increase its size from eight to 10 directors to include Dr. Guttentag and Ms. Lawrence, each of whom is “independent” as defined in the currently applicable listing standards of the NYSE and the rules and regulations of the SEC.

The standing committees of our Board are the Audit Committee, Compensation Committee, Nominating and Corporate Governance Committee, Academic Committee and Capital Allocation Committee. The specific functions and responsibilities of each committee are set forth in its charter. The charters of the Audit Committee, Compensation Committee and Nominating and Corporate Governance Committee are available on the Company’s website at https://investors.stridelearning.com/governance and are also available in print to any stockholder who requests them.

In October 2026, the Board established the Capital Allocation Committee to support and make recommendations to the Board regarding the Company’s capital structure and capital allocation strategy.

As of the date of this Proxy Statement, membership on the committees of the Board is as follows:

Immediately following the conclusion of the Annual Meeting, we expect membership on the committees of the Board to be as follows:

In furtherance of our goal to improve academic performance, the Board established the Academic Committee in September 2026 and appointed Mr. Smith as Chair of the Academic Committee. As a result of his new role as Chair of the Academic Committee and in light of the Board’s appointment of Brian A. Shepherd to the Audit Committee in July 2026, the Board and Mr. Smith mutually agreed that he should step down from the Audit Committee.

Membership on the committees described below is as of the date of this Proxy Statement.

The Nominating and Corporate Governance Committee may consider the following criteria, as well as any other factors it deems appropriate, in recommending candidates for election to our Board:

The Board strives to nominate directors with a variety of complementary skills so that, as a group, the Board will possess a mix of the appropriate backgrounds, perspectives, skills and expertise to oversee the Company’s business. Based upon voluntarily reported data, our current eight-member Board has one Hispanic director, two African American directors, five White directors, two female directors, and six male directors. The Nominating and Corporate Governance Committee will consider director candidates recommended by stockholders in the same manner and using the same criteria as for other candidates, provided such recommendations are submitted in writing not later than the close of business on the 90^th day, nor earlier than the close of business on the 120^th day, prior to the anniversary of the preceding year’s annual meeting of stockholders. Such recommendations should include the name and address and other pertinent information about the candidate as is required to be included in the Company’s proxy statement. Recommendations should be submitted to the Corporate Secretary of the Company at Stride, Inc., 11720 Plaza America Drive, 9th Floor, Reston, VA 20190, Attention: General Counsel and Secretary. The Nominating and Corporate Governance Committee will consider the criteria set forth above and other relevant information when evaluating director candidates recommended by stockholders.

Stockholders and other interested parties may communicate directly with our Board, individually or as a group, by sending an email to our General Counsel at OGC@K12.com, or by mailing a letter to Stride, Inc., 11720 Plaza America Drive, 9th Floor, Reston, VA 20190, Attention: General Counsel and Secretary. Our General Counsel will monitor these communications and provide summaries of all received communications to our Board at its regularly scheduled meetings. Where the nature of a communication warrants, our General Counsel may decide to seek the more immediate attention of the appropriate committee of the Board or an individual director, or our management or independent advisors and will determine whether any response is necessary.

Our Board is comprised of independent, accomplished and experienced directors who provide advice and oversight of management to further the interests of the Company and its stockholders. Our governance framework provides the Board with the flexibility to determine an optimal organizational structure for leadership and engagement while ensuring appropriate insight into, and oversight of, the operations, management and strategic issues of the Company.

On July 29, 2026, we appointed Robert E. Knowling, Jr., who previously served as an independent member of our Board, to serve as our CEO, succeeding James J. Rhyu, who ceased serving as CEO and as a member of the Board. We also appointed Steven B. Fink, who previously served as our Lead Independent Director, to serve as our Chair of the Board, effective July 29, 2026. The Board has evaluated its leadership structure and believes that the current leadership structure is appropriate and provides effective independent oversight of management.

Chief Executive Officer. Our Board elects a CEO who is responsible for the strategic direction and day-to-day leadership and performance of the Company, subject to the overall direction and supervision of the Board and its committees. The CEO is responsible for developing our culture and overall Company vision, managing, overseeing and evaluating the executive officers and other key employees that report directly to the CEO and serving as the principal external spokesperson for the Company. Our CEO is subject to an annual performance evaluation conducted by the Compensation Committee, which reviews, approves and recommends corporate goals and objectives relating to the compensation of our CEO and evaluates the CEO’s achievement of these goals. The Board Chair reviews the results of this annual performance evaluation with the CEO and the Chair of the Compensation Committee.

Board Chair. Our Board elects a chair from among the directors and determines whether to separate or combine the roles of Chair and CEO based on what it believes best serves the needs of the Company and its stockholders at any particular time. Both approaches have been taken depending on the circumstances, and this determination is communicated to stockholders. The determination to elect Mr. Fink as Board Chair was based on a number of factors that made him particularly well-suited for the role. These factors included his service as Chair of our Audit Committee and prior service as our Lead Independent Director, along with his significant experience in operations and financial oversight gained from serving as director and/or chairman for various public and private companies and his understanding of the Company’s business, growth opportunities, challenges and risk management practices. A key role of the Board Chair is to facilitate communications between the CEO and independent directors and the committees of the Board. The Board believes that the Board Chair will provide additional independent oversight of executive management and Board matters.

Role and Responsibilities of the Board Chair include:

Executive Sessions of the Board. Our Board holds executive sessions without management directors or management present at each regularly scheduled meeting of the Board. The

independent directors also may meet without management present at other times as requested by any independent director. The Board Chair has the authority to call meetings of the independent directors and chair executive sessions of the Board during which no members of management are present. These meetings are intended to provide the Board Chair with information that he can use to assist the CEO to function in the most effective manner. As Board Chair, Mr. Fink chairs the executive sessions of the Board.

Our Board believes full and open communication with management is essential for effective enterprise risk management and oversight. Members of our Board discuss strategy and risks facing the Company with our CEO and other members of our senior management at meetings of the Board, or when members of our Board seek to focus on a particular area of risk. Because our CEO and Board Chair set the agenda for Board meetings, each functional division of the Company can identify and bring to our Board’s or Board committees’ attention risk-related topics that may require added focus, which have included: evolving state curriculum standards, student engagement and retention, education technology, legal and policy matters, information security and succession planning. Our CEO also periodically presents to our Board on the strategic, financial and operational issues facing the Company, which frequently includes a review of associated risks and opportunities.

Management is responsible for identifying, prioritizing, remediating and monitoring the day-to-day management of risks that the Company faces and applying the Company’s disclosure controls and procedures, while our Board, as a whole and through its committees, is responsible for the oversight of enterprise risk management. In fiscal 2026, the Audit Committee continued to work directly with a major independent accounting firm to support the Company’s internal audit function in risk management. This combination provides us with the focus, scope, expertise, alignment and continuous attention necessary for effective risk management and disclosures.

While our Board is ultimately responsible for risk oversight, five of its committees concentrate on specific risk areas:

The Audit Committee oversees financial reporting and internal controls, school and corporate compliance, cybersecurity and operations risk and discusses with management the Company’s policies with respect to those matters. Our internal audit department prepares risk management reports that are provided to the Audit Committee on a quarterly basis, or as needed. The Audit Committee receives regular reports from management, including the Chief Information Security Officer, on our cybersecurity risks. In addition, management updates the Committee on any cybersecurity incidents it considers to be significant or potentially significant. The Audit Committee reports to the full Board regarding its activities, including those related to cybersecurity. In addition, the Audit Committee assists the Board in the oversight of legal risk management. A Legal Compliance and Ethics Committee (consisting of senior management members) maintains a Legal Compliance and Ethics Program, which includes a Chief Compliance Officer. The Legal Compliance and Ethics Committee provides reports to the Audit Committee on the Company’s legal risks and compliance-related matters in the schools we serve and at the corporate level.

Our Compensation Committee assists our Board in fulfilling its oversight responsibilities with respect to the management of risks arising from our compensation policies and programs for both executive and non-executive employees and retains outside compensation and legal experts for that purpose.

Our Nominating and Corporate Governance Committee assists our Board in fulfilling its oversight responsibilities with respect to the management of risks associated with the organization, membership and structure, or design, of the Board, succession planning and corporate governance.

Our Academic Committee assists our Board in fulfilling its oversight responsibilities with respect to regulatory risks specific to academics and associated state accountability standards.

Finally, our Capital Allocation Committee assists our Board in fulfilling its oversight responsibilities with respect to risks associated with the Company’s capital structure and capital allocation strategy.

The Board committees may retain independent counsel, experts or advisors as provided for in their charters, and the Board as a whole has access to such advisors and such other independent advisors that the Company retains or that the Board considers necessary to discharge its responsibilities, including in connection with risk oversight.

In fiscal 2026, pursuant to our Amended Non-Employee Directors Compensation Plan (“Directors Compensation Plan”), our non-employee directors were eligible to receive annual cash retainers for service on our Board and assigned committees and restricted stock awards. Mr. Rhyu, our former CEO, received no additional compensation for his service on our Board. Mr. Knowling received compensation for his service as a non-employee director during fiscal 2026, as reflected in the table below. Mr. Knowling is no longer eligible to be compensated under the Directors Compensation Plan following his appointment as our CEO.

Pursuant to the terms of the Directors Compensation Plan, in fiscal 2026, each non-employee director received an annual cash retainer of $70,000, the Lead Independent Director, if applicable, received an additional $50,000, the non-executive Chair of our Board, if applicable, received an additional $100,000, and each non-employee director received an additional amount for each committee on which the non-employee director serves, as shown below:

On the date of each annual meeting of stockholders, each non-employee director is eligible to receive an annual restricted stock award valued at $250,000 as of the grant date, with the shares of our Common Stock underlying such awards vesting fully on the earlier of (a) one year from the date of grant, or (b) the date of the next annual meeting of our stockholders occurring after the date of grant. In addition, the restricted stock awards vest on an accelerated basis upon a non-employee director’s termination of service by reason of death, disability or upon a change in control of the Company. The annual cash retainer, including the committee fees, and the annual restricted stock awards may be deferred in the form of deferred stock units under our Deferred Compensation Plan for Non-Employee Directors (“Directors Deferred Compensation Plan”).

In September 2026, the Board approved modifying the Directors Compensation Plan to reflect the establishment of the Academic Committee in September 2026. Any non-employee director who serves on the Academic Committee will receive an additional cash retainer of $10,000 per year, if they are a member, or $25,000 per year, if they are the chair.

In October 2026, the Board approved modifying the Directors Compensation Plan to reflect the establishment of the Capital Allocation Committee in October 2026. Any non-employee director who serves on the Capital Allocation Committee will receive an additional cash retainer of $10,000 per year, if they are a member, or $15,000 per year, if they are the chair (including co-chairs).

The following table sets forth the compensation paid to our non-employee directors for their services during fiscal 2026, including amounts that were deferred under the Directors Deferred Compensation Plan:

Please see the Security Ownership by Certain Beneficial Owners and Management table below for additional information on the beneficial ownership of our Common Stock by each of our directors.

The Company encourages each non-employee director to purchase shares of our Common Stock and to maintain a minimum ownership level during his or her tenure to foster alignment with our stockholders. To reinforce this objective, we maintain minimum director stock ownership guidelines for all of our non-employee directors. Pursuant to those guidelines, non-employee directors must hold shares of our Common Stock equal to five times the annual cash retainer. Non-employee directors must be in compliance with this policy by five years after they begin service on our Board. As of the date of this Proxy Statement, all of our non-employee directors are in compliance with this policy or are within the period to accumulate the specified level of ownership.

Our non-employee directors may elect, pursuant to our Directors Deferred Compensation Plan, to defer payment of all or a portion of their cash and equity compensation for service on our Board. In the case of a deferral of an equity award, the non-employee director is granted an equal amount of deferred stock units in lieu of restricted shares. Deferred stock units granted in lieu of a restricted stock award are subject to the same vesting requirements or other restrictions that would have applied to such restricted stock award.

In the case of a deferral of cash compensation, the non-employee director receives a number of deferred stock units equal to the amount of the cash compensation being deferred, divided by the per-share closing price of a share of our Common Stock on the date that the cash compensation would have been paid but for the deferral. Deferred stock units credited in lieu of cash compensation are fully vested.

Deferred stock units generally become payable, in a lump sum, within 90 days of the date the non-employee director no longer serves on our Board. Deferred stock units are settled in shares of our Common Stock or cash, at the Company’s discretion.

Our Board oversees the management of the Company and its business for the benefit of our stockholders in order to enhance stockholder value over the long term and to achieve its educational mission. The Board has adopted Corporate Governance Guidelines to assist it in the exercise of its responsibilities. The Guidelines are reviewed annually and periodically amended as the Board enhances the Company’s corporate governance practices. The Board has also adopted a Code of Business Conduct and Ethics that applies to all directors, officers and employees. The purpose of this code is to promote honest and ethical conduct for conducting the business of the Company, consistent with the highest standards of business ethics. The Corporate Governance Guidelines and Code of Business Conduct and Ethics are available on our website at https://investors.stridelearning.com/governance.

Our corporate governance and business conduct best practices include:

We intend to satisfy the disclosure requirements under the Securities Exchange Act of 1934, as amended (“Exchange Act”), regarding any amendment to, or waiver from a material provision of our Code of Business Conduct and Ethics involving our principal executive, financial or accounting officer or controller by posting such information on our website.

We recognize that related party transactions present a heightened risk of conflicts of interest and have adopted a written policy to which all related party transactions shall be subject. Pursuant to the policy, the Audit Committee of our Board, or in the case of a transaction in which the aggregate amount is, or is expected to be, in excess of $250,000, the Board, will review the relevant facts and circumstances of all related party transactions, including, but not limited to: (i) whether the transaction is on terms comparable to those that could be obtained in arm’s length

dealings with an unrelated third party; (ii) the extent of the related party’s interest in the transaction; and (iii) whether the transaction is consistent with the conflicts of interest and corporate opportunity provisions of the Company’s Code of Business Conduct and Ethics. Pursuant to the policy, no director, including the Chair of the Audit Committee, may participate in any approval of a related party transaction to which he or she is a related party. The Board or Audit Committee, as applicable, will then, in its sole discretion, either approve or disapprove the transaction.

Certain types of transactions, which would otherwise require individual review, have been pre-approved by the Audit Committee. These types of transactions include, for example: (i) compensation to an officer or non-employee director where such compensation is required to be disclosed in our proxy statement; (ii) transactions where the interest of the related party arises only by way of a directorship or minority stake in another organization that is a party to the transaction; and (iii) transactions involving competitive bids or fixed rates. Material related party transactions are required to be disclosed to the full Board. Additionally, pursuant to the terms of our related party transaction policy, all related party transactions are required to be disclosed in our applicable filings with the SEC, to the extent required by applicable SEC rules and regulations. We have established internal policies relating to disclosure controls and procedures, which include policies relating to the reporting of related party transactions that must be pre-approved under our related party transactions policy.

Pursuant to the Cooperation Agreement, the Company will reimburse the Investor Group for its out-of-pocket costs and expenses incurred on or prior to October 8, 2026, in connection with the subject matter of the Cooperation Agreement, subject to a maximum aggregate dollar cap of $1,200,000. Mr. Haggart is a member of our Board and serves as the managing partner of Fivespan and the managing member of Fivespan Partners GP, LLC, and Fivespan and Fivespan Partners GP, LLC are the investment manager and general partner of the investment manager, respectively.

During all or a portion of fiscal 2026, Messrs. Fink, Knowling and Verbrugge and Ms. Lawrence served on our Compensation Committee. During fiscal 2026, there were no interlocking relationships existing between members of our Board and our Compensation Committee and members of the board of directors or the compensation committee of any other company. No member that served on the Compensation Committee during all or a portion of fiscal 2026 was an officer or employee of the Company during fiscal 2026 or a former officer of the Company or has any relationship requiring disclosure by the Company under Item 404 of Regulation S-K. In addition, no executive officer of the Company served on any board of directors or compensation committee of any other entity whose executive officers served on the Compensation Committee or as a director of the Company at any time during fiscal 2026.

In accordance with a written charter adopted by the Board, the Audit Committee, or the “Committee,” assists the Board in fulfilling its responsibility for oversight of the quality and integrity of the Company’s financial reporting processes and its internal audit function. Management has the primary responsibility for the financial statements and the reporting process, including the system of internal controls and for assessing the effectiveness of the Company’s internal control over financial reporting. The independent auditors are responsible for performing an independent audit of the Company’s consolidated financial statements and internal control over financial reporting in accordance with the standards of the Public Company Accounting Oversight Board and for issuing reports thereon.

In this context, the Committee has met and held discussions with management, the independent auditors and internal audit, as well as legal counsel. Management represented to the

Committee that the Company’s consolidated financial statements were prepared in accordance with generally accepted accounting principles, and the Committee has reviewed and discussed the consolidated financial statements with management and the independent auditors. The Committee discussed with the independent auditors matters required to be discussed by the applicable requirements of the Public Company Accounting Oversight Board and the SEC.

In addition, the Committee has received the written disclosures and the letter from the independent auditors required by the applicable requirements of the Public Company Accounting Oversight Board regarding the independent accountant’s communications with the Committee concerning independence and has discussed with the independent auditors the auditors’ independence from the Company and its management.

The Committee discussed with the Company’s internal and independent auditors the overall scope and plans for their respective audits. The Committee meets with the internal and independent auditors, with and without management present, to discuss the results of their examinations, the evaluations of the Company’s internal controls and the overall quality of the Company’s accounting principles.

In reliance on the reviews and discussions referred to above, the Committee recommended to the Board, and the Board approved, the inclusion of the audited financial statements of the Company for the fiscal year ended June 30, 2026, in the Company’s Annual Report on Form 10-K for the fiscal year ended June 30, 2026, filed with the SEC on August 4, 2026.

The foregoing report is not “soliciting material,” shall not be deemed “filed” and shall not be deemed incorporated by reference by any general statement incorporating by reference this Proxy Statement into any filing under the Securities Act of 1933, as amended, or under the Exchange Act (together, the “Acts”), except to the extent that the Company specifically incorporates this information by reference, and shall not otherwise be deemed filed under the Acts.

KPMG was the Company’s independent registered public accounting firm for the fiscal years ended June 30, 2026 and June 30, 2025 (“fiscal 2025”). The following table presents fees for professional services rendered to the Company by KPMG for our fiscal 2026 and fiscal 2025:

Audit fees are for professional services for the Company’s annual audit, including the audit of internal control over financial reporting for fiscal 2026 and fiscal 2025, reviews of the interim financial statements included in the Company’s quarterly reports on Form 10-Q, and other professional services provided in connection with statutory and regulatory filings or engagements. In fiscal 2026, Tax Fees include permissible compliance services provided for one of the Company’s international subsidiaries.

The Audit Committee maintains policies and procedures for the pre-approval of work performed by the independent auditors in that, under the Audit Committee charter, all auditor engagements must be approved in advance by the Audit Committee. All of the services provided to the Company by KPMG during fiscal 2026 and fiscal 2025 were pre-approved by the Audit Committee.

The Audit Committee has appointed KPMG as the Company’s independent registered public accounting firm for our fiscal year ending June 30, 2027. Although ratification is not required by law, our Board believes that our stockholders should be given the opportunity to express their view on the subject. While not binding on the Audit Committee, if our stockholders do not ratify this appointment, the appointment will be reconsidered by the Audit Committee. Even if the appointment is ratified, the Audit Committee, in its discretion, may appoint a different independent registered public accounting firm at any time during the year if it determines that such a change would be in the best interests of the Company and our stockholders. A representative of KPMG is expected to attend the Annual Meeting, and this representative will be provided with an opportunity to make a statement, if he or she desires, and will be available to respond to appropriate questions from stockholders, if any.

As previously disclosed in our Current Report on Form 8-K filed on August 20, 2024, on August 15, 2024, the Audit Committee approved the engagement of KPMG as the Company’s independent registered public accounting firm for fiscal 2025 and the dismissal of BDO USA, P.C. (“BDO”) as the Company’s independent registered public accounting firm, each effective immediately.

BDO’s reports on the Company’s consolidated financial statements and internal control over financial reporting, which were included in the Company’s Annual Report on Form 10-K for the fiscal year ended June 30, 2024 (“fiscal 2024”), and reports on the Company’s consolidated financial statements and internal control over financial reporting, which were included in the Company’s Annual Report on Form 10-K for the fiscal year ended June 30, 2023 (“fiscal 2023”), did not contain an adverse opinion or disclaimer of opinion and were not qualified or modified as to uncertainty, audit scope or accounting principles, except that the reports of BDO dated August 15, 2023 noted that BDO audited the Company’s internal control over financial reporting as of June 30, 2023 and expressed an adverse opinion thereon due to a material weakness in internal control over financial reporting relating to a lack of effective information technology general controls related to user access, program change, and data processing over information technology systems used by the Company for financial reporting.

During fiscal 2024 and fiscal 2023, and the subsequent interim period through August 15, 2024, there were: (i) no disagreements within the meaning of Item 304(a)(1)(iv) of Regulation S-K between the Company and BDO on any matter of accounting principles or practices, financial statement disclosure, or auditing scope or procedure, which, if not resolved to BDO’s satisfaction, would have caused BDO to make reference thereto in BDO’s reports; and (ii) other than the material weakness noted above, no “reportable events” within the meaning of Item 304(a)(1)(v) of Regulation S-K.

During fiscal 2024 and fiscal 2023, and the subsequent interim period through August 15, 2024, neither the Company nor anyone on its behalf has consulted with KPMG regarding: (i) the application of accounting principles to a specific transaction, either completed or proposed, or the type of audit opinion that might be rendered on the Company’s financial statements, and neither a written report nor oral advice was provided to the Company that KPMG concluded was an important factor considered by the Company in reaching a decision as to any accounting, auditing, or financial reporting issue; (ii) any matter that was the subject of a disagreement within the meaning of Item 304(a)(1)(iv) of Regulation S-K; or (iii) any “reportable event” within the meaning of Item 304(a)(1)(v) of Regulation S-K.

The affirmative vote of the holders of a majority in voting power held by the stockholders present in person or represented by proxy at the Annual Meeting is required to ratify the appointment of KPMG as the Company’s independent registered public accounting firm.

OUR BOARD RECOMMENDS YOU VOTE “FOR” THE RATIFICATION OF THE APPOINTMENT OF KPMG AS THE COMPANY’S INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM FOR THE FISCAL YEAR ENDING JUNE 30, 2027.

In accordance with Section 14A of the Exchange Act, we are asking our stockholders to cast a non-binding advisory vote to approve the fiscal 2026 compensation of our NEOs, as disclosed in this Proxy Statement. This proposal, commonly known as a “Say-on-Pay” proposal, gives our stockholders the opportunity to express their views on the design and effectiveness of our executive compensation program.

As described in detail under the heading “Compensation Discussion and Analysis,” our executive compensation program is designed to attract, motivate and retain our NEOs, who are critical to our success. Under this program, our NEOs are rewarded for the achievement of specific annual, long-term and strategic goals, and the realization of increased stockholder value. Please read the “Compensation Discussion and Analysis” and the compensation tables that follow for additional details about our executive compensation program, including information about the fiscal 2026 compensation of our NEOs, our engagement with stockholders in fiscal 2026 relating to our executive compensation program and the responsive actions we have taken in and subsequent to fiscal 2026.

We are asking our stockholders to indicate their support for the compensation of our NEOs as described in this Proxy Statement. This vote is not intended to address any specific item of compensation, but rather the overall compensation of our NEOs and the philosophy, policies and practices described in this Proxy Statement. Accordingly, we ask our stockholders to vote FOR the following resolution:

“RESOLVED, that the compensation paid to the Company’s named executive officers, as disclosed pursuant to Item 402 of Regulation S-K, including the Compensation Discussion and Analysis, compensation tables and related narrative discussion is hereby APPROVED.”

The Say-on-Pay vote is advisory and, therefore, not binding on the Company, our Compensation Committee, or our Board. Our Board and our Compensation Committee value the opinions of our stockholders, and to the extent there is a significant vote against the NEO compensation, as disclosed in this Proxy Statement, we will consider our stockholders’ concerns and will evaluate what, if any, further actions are necessary to address those concerns. We expect to hold our next Say-on-Pay vote at our 2027 Annual Meeting.

The affirmative vote of the holders of a majority in voting power held by the stockholders present in person or represented by proxy at the Annual Meeting is required to approve the compensation of our NEOs.

OUR BOARD RECOMMENDS YOU VOTE “FOR” THE NON-BINDING ADVISORY RESOLUTION APPROVING THE COMPENSATION OF OUR NEOs, AS DISCLOSED IN THIS PROXY STATEMENT PURSUANT TO THE COMPENSATION DISCLOSURE RULES OF THE SEC.

The following table sets forth, as of October 19, 2026, certain information with respect to the beneficial ownership of Common Stock by each beneficial owner of more than 5% of the Company’s voting securities (based solely on review of filings with the SEC), each director and each NEO and all directors and executive officers of the Company as a group, except as qualified by the information set forth in the notes to this table. To our knowledge, except as noted below, no person or entity is the beneficial owner of more than 5% of the voting power of the Company’s voting securities. As of October 19, 2026, 42,048,853 shares of our Common Stock were outstanding.

Unless otherwise noted, the address for each director and executive officer is c/o Stride, Inc., 11720 Plaza America Drive, 9th Floor, Reston, VA 20190.

This section sets forth the objectives and elements of our executive compensation program, describes the related processes of our Compensation Committee (the “Committee”) and discusses the compensation earned or received by and paid to our NEOs for fiscal 2026. For fiscal 2026, our NEOs and their positions were:

Fiscal 2026 was a year of meaningful progress for Stride. We continue to see strong demand for our programs, made progress on a number of strategic priorities and delivered solid financial results and operational performance. We achieved our 10th straight year of revenue growth and delivered record profitability. Sustained demand for our online educational solutions led to year-over-year enrollment growth of just over 4%. We increased net income by more than 17% and Adjusted EBITDA by more than 8%.¹ We believe that our business remains uniquely positioned to help the academic community by offering a meaningful education experience for students, families and school districts, as the world continues to change.

From our inception in 1999, we have offered curriculum, instructional support services and products through our educational platform, which is designed to facilitate individualized learning for students in kindergarten through 12^th grade. We have also expanded our offerings to address the nation’s growing skills and labor gap.

Looking ahead, we are well positioned to build on this progress under new leadership. In July 2026, Robert E. Knowling, Jr. was appointed as our CEO. Mr. Knowling has a 30-year track record leading business transformation, improving operating execution, and successfully scaling organizations across the education and technology sectors. Under the oversight of the Board, Mr. Knowling has initiated a comprehensive review spanning the Company’s strategy, operations,

technology and capital allocation, focused on ensuring that the right priorities, initiatives, and organizational structure are in place to best position the Company for profitable growth and to deliver on its mission of helping learners of all ages reach their potential through inspired teaching and personalized learning.

The Committee believes that performance-based compensation incentivizes our executive officers to promote the overall success of our business and aligns management’s interests with those of our stockholders. Consistent with this philosophy, we reward our executive officers for great performance relative to our key financial and operational metrics that drive stockholder value creation.

Fiscal 2026 highlights include:

Our executive compensation program for fiscal 2026 largely retained the same design used in fiscal 2025.

The following charts illustrate the target total direct compensation mix of our former CEO and our other NEOs for fiscal 2026. These charts show that a majority of our NEOs’ target total direct compensation opportunities was performance-based (70% for Mr. Rhyu and an average of 58% for our other NEOs).

We employ certain policies and practices to align our executive officers’ compensation with stockholder interests. Listed below are the key compensation policies and practices we employ and certain policies and practices we do not employ because we believe they would not serve the long-term interests of our stockholders.