Root, 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. )

Filed by the Registrant☒

Filed by a Party other than the Registrant☐

Check the appropriate box:

☐Preliminary Proxy Statement

☐Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

☒Definitive Proxy Statement

☐Definitive Additional Materials

☐Soliciting Material Pursuant to § 240.14a-12

ROOT, 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):

☒No fee required

☐Fee paid previously with preliminary materials

☐Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11

Root, Inc.

80 E. Rich Street, Suite 500

Columbus, Ohio 43215

(866) 980-9431

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

To Be Held On June 3, 2026

To the Stockholders of Root, Inc.:

On behalf of our board of directors, it is our pleasure to cordially invite you to attend the 2026 Annual Meeting of

Stockholders (the “Annual Meeting”) of Root, Inc., a Delaware corporation (the “Company”). The Annual Meeting

will be held virtually, via live webcast atwww.virtualshareholdermeeting.com/ROOT2026, originating from

Columbus, Ohio, on Wednesday, June 3, 2026, at 11:00 a.m. Eastern Daylight Time. We believe hosting a virtual

meeting enables participation by more of our stockholders, while lowering the cost of conducting the meeting.

Stockholders attending the virtual meeting may participate and vote online during the virtual meeting. We encourage

you to attend online and participate. We recommend that you log in a few minutes before 11:00 a.m. Eastern

Daylight Time, on June 3, 2026, to ensure you are logged in when the Annual Meeting starts.

The Annual Meeting will be held for the following purposes:

1. To elect three Class III directors, Lawrence Hilsheimer, Alexander Timm and Douglas Ulman,

each to hold office until our Annual Meeting of Stockholders in 2029;

2. To ratify the selection by the audit, risk and finance committee of our board of directors of

Deloitte & Touche LLP as our independent registered public accounting firm for the fiscal year

ending December 31, 2026;

3. To approve, on an advisory basis, our named executive officer compensation;

4. To approve an amendment to the Company’s Amended and Restated Certificate of Incorporation,

as amended, to allow for exculpation of certain officers; and

5. To conduct any other business properly brought before the Annual Meeting.

These items of business are more fully described in the Proxy Statement accompanying this Notice.

The record date for the Annual Meeting is April 6, 2026. Only stockholders of record at the close of business on that

date may vote at the Annual Meeting or any adjournment thereof.

By Order of the Board of Directors,

Jodi E. Baker

Chief Legal Officer and Secretary

Columbus, Ohio

April 24, 2026

You are cordially invited to attend the Annual Meeting. Whether or not you expect to attend the Annual Meeting, PLEASE VOTE YOUR SHARES. As an alternative to voting online at the Annual Meeting, you may vote your shares in advance of the Annual Meeting through the internet, by telephone or, if you receive a paper proxy card in the mail, by mailing the completed proxy card. Voting instructions are provided in the Notice of Internet Availability of Proxy Materials or, if you receive a paper proxy card by mail, the instructions are printed on your proxy card. Even if you have voted by proxy, you may still vote online if you attend the Annual Meeting. Please note, however, that if your shares are held of record by a broker, bank or other agent and you wish to vote at the Annual Meeting, you must follow the instructions from such organization.

TABLE OF CONTENTS

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Root, Inc.

80 E. Rich Street, Suite 500

Columbus, Ohio 43215

(866) 980-9431

PROXY STATEMENT

FOR THE 2026 ANNUAL MEETING OF STOCKHOLDERS

To Be Held on June 3, 2026 at 11:00 a.m. Eastern Daylight Time

Our board of directors is soliciting your proxy to vote at the 2026 Annual Meeting of Stockholders (the “Annual

Meeting”) of Root, Inc., a Delaware corporation, to be held virtually, via live webcast at

www.virtualshareholdermeeting.com/ROOT2026, originating from Columbus, Ohio, on Wednesday, June 3, 2026,

at 11:00 a.m. Eastern Daylight Time and any adjournment or postponement thereof. We believe hosting a virtual

meeting enables participation by more of our stockholders, while lowering the cost of conducting the meeting.

Stockholders attending the virtual meeting may participate and vote online during the virtual meeting.

For the Annual Meeting, we have elected to furnish our proxy materials, including this proxy statement (the “Proxy

Statement”) and our Annual Report on Form 10-K for the fiscal year ended December 31, 2025 (the “Annual

Report”), to our stockholders primarily via the internet. On or about April 24, 2026, we expect to mail to our

stockholders a Notice of Internet Availability of Proxy Materials (the “Notice”) that contains notice of the Annual

Meeting and instructions on how to access our proxy materials on the internet, how to vote at the Annual Meeting

and how to request printed copies of the proxy materials. Stockholders may request to receive all future materials in

printed form by mail or by email by following the instructions contained in the Notice. A stockholder’s election to

receive proxy materials by mail or email will remain in effect until revoked. We encourage stockholders to take

advantage of the availability of the proxy materials on the internet to help reduce the environmental impact and cost

of our Annual Meeting.

Only stockholders of record at the close of business on April 6, 2026 (the “Record Date”) will be entitled to vote at

the Annual Meeting. On the Record Date, there were 14,015,900 shares of Class A common stock,1,806,236 shares

of Class B common stock and 14,053,096 shares of Series A Convertible Preferred Stock (the “Series A preferred

stock”) outstanding and entitled to vote. Each holder of Class A common stock will have the right to one vote

per share of Class A common stock and each holder of Class B common stock will have the right to 10 votes

per share of Class B common stock. The holder of the Series A preferred stock is entitled to vote with the

holders of Class A common stock and will have the right to one vote per each share of Class A common stock

into which the Series A preferred stock is convertible, or 780,727 votes. The holders of shares of Class A

common stock, Class B common stock and Series A preferred stock will vote together as a single class on all matters

submitted to a vote at the Annual Meeting. A list of stockholders entitled to vote at the Annual Meeting will be

available for examination for 10 days before the Annual Meeting at our address above. If you would like to view the

list, please contact our Secretary at proxy@joinroot.com to schedule an appointment. The stockholder list will also

be available online during the Annual Meeting. For instructions on how to attend the Annual Meeting, please see the

instructions atwww.virtualshareholdermeeting.com/ROOT2026 and on page 2 of this Proxy Statement. You will

not be able to attend the Annual Meeting in person.

In this Proxy Statement, we refer to Root, Inc. as “Root,” the “Company,” “we” or “us” and the board of directors of

Root as the, or our, “board of directors.” The Annual Report, which contains consolidated financial statements as of

and for the fiscal year ended December 31, 2025, accompanies this Proxy Statement. You also may obtain a copy of

the Annual Report without charge by emailing proxy@joinroot.com.