Stride, Inc.

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of

the Securities Exchange Act of 1934 (Amendment No. )

STRIDE, INC.

(Name of Registrant as Specified in its Charter)

(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)

Payment of Filing Fee (Check all boxes that apply):

Stride, Inc.

11720 Plaza America Drive

9th Floor

Reston, VA 20190

October 27, 2026

Dear Fellow Stockholders:

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.

NOTICE OF 2026 ANNUAL MEETING OF STOCKHOLDERS

December 10, 2026

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.

Sincerely,

Robert E. Knowling, Jr.

Chief Executive Officer

Reston, VA

October 27, 2026

Important Notice Regarding the Availability of Proxy Materials for the Stockholder

Meeting to be Held on December 10, 2026:

The Company’s 2026 Proxy Statement and the 2026 Annual Report are available at

www.proxyvote.com

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 or voting instruction form.