ROOT / Root, Inc. - Pemfailan SEC, Laporan Tahunan, Penyata Proksi

Root, Inc.
US ˙ NasdaqGS ˙ US77664L2079

Statistik Asas
CIK 1788882
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Root, Inc.
SEC Filings (Chronological Order)
Halaman ini menyediakan senarai kronologi lengkap bagi Pemfailan SEC, tidak termasuk pemfailan pemilikan yang kami sediakan di tempat lain.
August 6, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

August 6, 2025 EX-10.4

ployee Director Compensation Policy adopted May 1, 2025

Exhibit 10.4 Root, Inc. Non-Employee Director Compensation Policy Adopted May 1, 2025 Each member of the Board of Directors (the “Board”) of Root, Inc. (the “Company”) who is not an employee of the Company (each, a “Non-Employee Director”) will receive the compensation described in this Non-Employee Director Compensation Policy (this “Director Compensation Policy”) for his or her Board service, su

August 6, 2025 EX-99.1

Gross accident period loss ratio

Q2 2025 Shareholder Letter Letter to Shareholders: Q2 2025 Key quarterly metrics Dear Shareholders Dear Root Shareholders, The second quarter was another strong quarter for Root.

August 6, 2025 EX-10.2

Amended and Restated Form of Root, Inc. 2020 Equity Incentive Plan Performance-Based RSU Award Grant Notice and Agreement Retirement-Eligible (2024 Grant)

Exhibit 10.2 ROOT, INC. 2020 EQUITY INCENTIVE PLAN Amended and Restated AWARD AGREEMENT (Performance-Based RSU AWARD) As reflected by your Restricted Stock Unit Grant Notice (“Grant Notice”), Root, Inc. (the “Company”) has granted you a RSU Award under its 2020 Equity Incentive Plan (the “Plan”) for the number of performance-based restricted stock units as indicated in your Grant Notice (the “RSU

August 6, 2025 EX-10.1

Amended and Restated Form of Root, Inc. 2020 Equity Incentive Plan Performance-Based RSU Award Grant Notice and Agreement (2024 Grant)

Exhibit 10.1 ROOT, INC. 2020 EQUITY INCENTIVE PLAN AMENDED AND RESTATED AWARD AGREEMENT (Performance-Based RSU AWARD) As reflected by your Restricted Stock Unit Grant Notice (“Grant Notice”), Root, Inc. (the “Company”) has granted you a RSU Award under its 2020 Equity Incentive Plan (the “Plan”) for the number of performance-based restricted stock units as indicated in your Grant Notice (the “RSU

August 6, 2025 EX-10.3

Policy for the Acceleration of Equity Awards in the Event of Death

Exhibit 10.3 Policy for the Acceleration of Equity Awards in the Event of Death Effective April 30, 2025 Whereas, the Company has adopted and maintains the 2020 Equity Incentive Plan (the “2020 Plan”) and preceding 2015 Equity Incentive Plan (the “2015 Plan”) for the purposes of providing equity incentives to “Participants” (as such term is defined in the 2020 Plan and 2015 Plan, as applicable); W

August 6, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 6, 2025 ROOT, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 6, 2025 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

June 6, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 4, 2025 ROOT, INC. (Exact na

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 4, 2025 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

June 5, 2025 S-8

As filed with the Securities and Exchange Commission on June 5, 2025

As filed with the Securities and Exchange Commission on June 5, 2025 Registration No.

June 5, 2025 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Root, Inc (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity 2020 Equity Incentive Plan Class A Common Stock, par value $0.

May 7, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 7, 2025 ROOT, INC. (Exact nam

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 7, 2025 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (IR

May 7, 2025 EX-10.2

Form of Root, Inc. Non-Employee Director Compensation Policy

Exhibit 10.2 Root, Inc. Non-Employee Director Compensation Policy Restricted Stock Unit Deferral Election Form For Eligible Directors Please complete and return this Restricted Stock Unit Deferral Election Form (the “Election Form”), as described below, [for existing non-employee directors making elections for 2024: within 30 days after the Effective Date of the Policy] [for existing non-employee

May 7, 2025 EX-99.1

CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED

Q1 2025 Shareholder Letter Letter to Shareholders: Q1 2025 Key quarterly metrics Dear Shareholders The first quarter of 2025 was another great quarter for Root.

May 7, 2025 EX-10.1

Root, Inc. Non-Employee Director Compensation Policy

Exhibit 10.1 Root, Inc. Non-Employee Director Compensation Policy Adopted February 20, 2025 Each member of the Board of Directors (the “Board”) of Root, Inc. (the “Company”) who is not an employee of the Company (each, a “Non-Employee Director”) will receive the compensation described in this Non-Employee Director Compensation Policy (this “Director Compensation Policy”) for his or her Board servi

May 7, 2025 EX-10.3

2025 Short-Term Incentive Plan

Exhibit 10.3 2025 Root Short-Term Incentive Plan This 2025 Short-Term Incentive Plan (the “Plan”) of Root, Inc. (the “Company”) covers the period from January 1, 2025 through December 31, 2025. The purpose of the Plan is to promote the success of the Company by rewarding eligible employees for outstanding business results and to motivate employees in a high-performance culture. For 2025, incentive

May 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

April 25, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION 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)

April 25, 2025 DEF 14A

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. )

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)) ☒ Defin

February 26, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d)OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission file number 001-39658 ROOT, INC. (Exact

February 26, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 26, 2025 ROOT, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 26, 2025 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

February 26, 2025 EX-10.34

Executive Employment Agreement with Jon Allison

Exhibit 10.34 EXECUTIVE EMPLOYMENT AGREEMENT THIS EXECUTIVE EMPLOYMENT AGREEMENT (this “Agreement”) is made as of November 8, 2021, (the “Effective Date”), between Caret Holdings, Inc, a Delaware corporation (and collectively with its parents, subsidiaries, and other corporate affiliates, and its or their successors or assigns (the “Company”), and Jon Allison (“Executive”). The Company and Executi

February 26, 2025 EX-10.28

2024 Short-Term Incentive Plan

Exhibit 10.28 2024 Root Short-Term Incentive Plan This 2024 Short-Term Incentive Plan (the “Plan”) of Root, Inc. (the “Company”) covers the period from January 1, 2024 through December 31, 2024. The purpose of the Plan is to promote the success of the Company by rewarding employees for outstanding business results, as well as motivating employees in a high-performance culture. For 2024, incentive

February 26, 2025 EX-99.1

Gross accident period loss ratio

Q4 2024 Shareholder Letter Dear Root Shareholders 2024 was a landmark year for Root.

February 26, 2025 EX-97.1

Root, Inc. Compensation Recovery Policy

Exhibit 97.1 Root, Inc. Compensation Recovery Policy Originally Effective October 23, 2023 (the “Original Effective Date”) As Amended October 22, 2024 1.Purpose. The purpose of this Compensation Recovery Policy (this “Policy”) is to describe the circumstances under which Root, Inc. (the “Company”) is required to recover certain compensation paid to certain employees in certain circumstances, inclu

February 26, 2025 EX-19.1

Amended and Restated Ins

Exhibit 19.1 Root, Inc. AMENDED AND RESTATED Insider Trading Policy Approved by the Board of Directors October 23, 2024 Policy Principles 1.Personnel of Root, Inc. and its subsidiaries (together, “Root”) are responsible for understanding the obligations that come with having access to material nonpublic information and wanting to transact in Root securities. 2.Root personnel who are aware of mater

February 26, 2025 EX-21.1

List of subsidiaries of Root, Inc.

Exhibit 21.1 Subsidiaries of Root, Inc. Name Jurisdiction Caret Holdings, Inc. Delaware Root Enterprise, LLC Delaware Root Insurance Agency, LLC Ohio Root Insurance Company Ohio Root Lone Star Insurance Agency, Inc. Texas Root Property & Casualty Insurance Company Ohio Root Reinsurance Company, Ltd. Cayman Islands Root Scout, LLC Delaware Root Florida Insurance Company Florida

November 15, 2024 EX-10.2

Form of Root, Inc. 2020 Equity Incentive Plan Performance-Based RSU Award Grant Notice and Agreement Retirement-Eligible (2024 Grant)

ROOT, INC. PERFORMANCE-BASED RSU AWARD GRANT NOTICE (2020 EQUITY INCENTIVE PLAN) Root, Inc. (the “Company”) has awarded to you (the “Participant”) the number of restricted stock units specified and on the terms set forth below in consideration of your services (the “RSU Award”). Your RSU Award is subject to all of the terms and conditions as set forth herein and in the Company’s 2020 Equity Incent

November 15, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 13, 2024 ROOT, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 13, 2024 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

November 15, 2024 EX-10.1

Form of Root, Inc. 2020 Equity Incentive Plan Performance-Based RSU Award Grant Notice and Agreement (2024 Grant)

ROOT, INC. PERFORMANCE-BASED RSU AWARD GRANT NOTICE (2020 EQUITY INCENTIVE PLAN) Root, Inc. (the “Company”) has awarded to you (the “Participant”) the number of restricted stock units specified and on the terms set forth below in consideration of your services (the “RSU Award”). Your RSU Award is subject to all of the terms and conditions as set forth herein and in the Company’s 2020 Equity Incent

November 14, 2024 EX-99.1

99.1: Joint Filing Statement

EX-99.1 2 tm2427620d7ex99-1.htm EXHIBIT 99.1 CUSIP No. 77664L 10 8 13G Exhibit 99.1 AGREEMENT Pursuant to Rule 13d-1(k)(1) under the Securities Exchange Act of 1934, as amended, the undersigned hereby agree that only one statement containing the information required by Schedule 13G need be filed with respect to the ownership by each of the undersigned of common stock of Root, Inc. Dated: November

November 14, 2024 SC 13G/A

ROOT / Root, Inc. / Redpoint Omega II, L.P. - SC 13G/A Passive Investment

SC 13G/A 1 tm2427620d7sc13ga.htm SC 13G/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3) * Root, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 77664L 20 7 (CUSIP Number) September 30, 2024 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the ru

November 14, 2024 SC 13G/A

ROOT / Root, Inc. / Bullfrog Capital GP, Ltd. - SC 13G/A Passive Investment

SC 13G/A 1 tm2428285d2sc13ga.htm SC 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. 2)* Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 77664

October 30, 2024 EX-4.5

First Amendment to Form of Common Stock Purchase Warrant (Tranche 1), dated October 29, 2024

Exhibit 4.5 AMENDMENT NO. 1 TO COMMON STOCK PURCHASE WARRANT OF ROOT, INC. This AMENDMENT NO. 1 TO COMMON STOCK PURCHASE WARRANT OF ROOT, INC., a Delaware corporation (the “Company”), dated as of October 29, 2024 (this “Amendment”) is executed on behalf of the Company and the Holder (as identified on the signature pages hereto) pursuant to Section 6(p) of the Warrant (as defined below). Capitalize

October 30, 2024 EX-10.3

Amended and restated Board Observation Side Letter

Root, Inc. 80 E. Rich Street, Suite 500 Columbus, OH 43215 October 29, 2024 Ladies and Gentlemen: Reference is made to (i) that certain Term Loan Agreement, originally dated as of January 26, 2022 (as amended by First Amendment to Term Loan Credit Agreement dated as of September 17, 2024 and Limited Consent and Second Amendment to Term Loan Credit Agreement dated as of the date hereof, and as furt

October 30, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT,

October 30, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 30, 2024 ROOT, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 30, 2024 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number

October 30, 2024 EX-99.2

Root Announces Successful Refinancing of Term Loan Facility with BlackRock Improved Terms Enhance Company's Financial Flexibility and Improve Cost of Capital

Root Announces Successful Refinancing of Term Loan Facility with BlackRock Improved Terms Enhance Company's Financial Flexibility and Improve Cost of Capital COLUMBUS, Ohio, October 30, 2024 (GLOBE NEWSWIRE) — Root, Inc.

October 30, 2024 EX-10.2

and among the Company, Caret Holdings, Inc., as borrower, the loan parties party thereto and Acquiom Agency Services LLC, as the administrative agent for the lenders party thereto

LIMITED CONSENT AND SECOND AMENDMENT to TERM LOAN CREDIT AGREEMENT This LIMITED CONSENT AND SECOND AMENDMENT TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of October 29, 2024 is made by and among CARET HOLDINGS, INC.

October 30, 2024 EX-10.1

, by and among the Company, Caret Holdings, Inc., as borrower, the loan parties party thereto and Acquiom Agency Services LLC, as the administrative agent for the lenders party thereto

Exhibit 10.1 Executed Version FIRST AMENDMENT to TERM LOAN CREDIT AGREEMENT This FIRST AMENDMENT (this "Amendment"), dated as of September 17, 2024 is made by and among CARET HOLDINGS, INC., a Delaware corporation (the "Borrower"), the other Loan Parties party hereto, the Lenders party hereto (the "Required Lenders") and Acquiom Agency Services LLC, as Administrative Agent (the "Administrative Age

October 30, 2024 EX-99.1

Gross accident period loss ratio

Q3 2024 Shareholder Letter Dear Shareholders For the first time in company history, Root reached net income profitability.

August 9, 2024 SC 13D/A

ROOT / Root, Inc. / CARVANA GROUP, LLC - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 7) * Root, Inc. (Name of Issuer) Class A common stock, $0.0001 par value per share (Title of Class of Securities) 77664L108 (CUSIP Number) Ernest Garcia III President, Chief Executive Officer and Chairman 300 E. Rio Salado Parkway Tempe, Arizona 85281 (602

August 7, 2024 EX-10.1

2024 Short-Term Incentive Plan

2024 Root Short-Term Incentive Plan This 2024 Short-Term Incentive Plan (the “Plan”) of Root, Inc.

August 7, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

August 7, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 7, 2024 ROOT, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 7, 2024 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

August 7, 2024 EX-99.1

Gross accident period loss ratio

Q2 2024 Shareholder Letter Dear Shareholders Our team delivered another strong quarter in Q2, as we again demonstrated our ability to drive toward sustained profitability.

June 10, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 5, 2024 ROOT, INC. (Exact na

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 5, 2024 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

May 30, 2024 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 30, 2024 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

May 29, 2024 S-8

As filed with the Securities and Exchange Commission on May 29, 2024

As filed with the Securities and Exchange Commission on May 29, 2024 Registration No.

May 29, 2024 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Root, Inc (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity 2020 Equity Incentive Plan Class A Common Stock, par value $0.

May 7, 2024 SC 13D/A

ROOT / Root, Inc. / CARVANA GROUP, LLC - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 6) * Root, Inc. (Name of Issuer) Class A common stock, $0.0001 par value per share (Title of Class of Securities) 77664L108 (CUSIP Number) Ernest Garcia III President, Chief Executive Officer and Chairman 300 E. Rio Salado Parkway Tempe, Arizona 85281 (602

April 30, 2024 EX-99.1

Gross accident period loss ratio

Q1 2024 Shareholder Letter Dear Shareholders We’re pleased to share that our strong momentum continued in the first quarter of 2024, delivering operating income for the first time in the company’s history while materially growing our business.

April 30, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

April 30, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 30, 2024 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

April 26, 2024 DEF 14A

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. )

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)) ☒ Defin

April 26, 2024 DEFA14A

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. )

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)) ☐ Defin

April 16, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 15, 2024 ROOT, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 15, 2024 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

April 3, 2024 EX-99.1

Meet Root 2024 Company Overview Confidential | Do Not Distribute Forward-looking statements This presentation contains forward-looking statements relating to, among other things, the future performance of Root and its consolidated subsidiaries that a

investorresourcedeck2024 Meet Root 2024 Company Overview Confidential | Do Not Distribute Forward-looking statements This presentation contains forward-looking statements relating to, among other things, the future performance of Root and its consolidated subsidiaries that are based on Root’s current expectations, forecasts, and assumptions, and involve risks and uncertainties.

April 3, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 3, 2024 ROOT, INC. (Exact n

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 3, 2024 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (

March 20, 2024 SC 13G/A

ROOT / Root, Inc. / Schusterman Interests, LLC - SCHEDULE 13G/A, AMENDMENT #1 Passive Investment

SC 13G/A 1 s72492074.htm SCHEDULE 13G/A, AMENDMENT #1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* Root, Inc. (Name of Issuer) Class A common stock, par value $0.0001 per share (Title of Class of Securities) 77664L207 (CUSIP Number) March 19, 2024 (Date of Event which Requires Filing of this State

February 21, 2024 EX-97.1

Root, Inc. Compensation Recovery Policy

EXHIBIT 97.1 Root, Inc. Compensation Recovery Policy Effective October 23, 2023 1.Purpose. The purpose of this Compensation Recovery Policy (this “Policy”) is to describe the circumstances under which Root, Inc. (the “Company”) is required to recover certain compensation paid to certain employees. Any references in compensation plans, agreements, equity awards, or other policies to the Company’s “

February 21, 2024 EX-21.1

List of subsidiaries of Root, Inc.

Exhibit 21.1 Subsidiaries of Root, Inc. Name Jurisdiction Caret Holdings, Inc. Delaware Root Enterprise, LLC Delaware Root Insurance Agency, LLC Ohio Root Insurance Company Ohio Root Lone Star Insurance Agency, Inc. Texas Root Property & Casualty Insurance Company Ohio Root Reinsurance Company, Ltd. Cayman Islands Root Scout, LLC Delaware

February 21, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d)OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission file number 001-39658 ROOT, INC. (Exact

February 21, 2024 EX-4.2

Description of Securities

Exhibit 4.2 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 Root, Inc. had one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”): our Class A common stock, $0.0001 par value per share (“Class A Common Stock”). References herein to the terms “we,” “our” and “us”

February 21, 2024 EX-99.1

Gross accident period loss ratio

Q4 2023 Shareholder Letter Dear Root Shareholders 2023 was a transformative year for Root.

February 21, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 21, 2024 ROOT, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 21, 2024 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

February 14, 2024 SC 13G/A

ROOT / Root, Inc. / SVB FINANCIAL GROUP - SC 13G/A Passive Investment

SC 13G/A 1 d789021dsc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 3)* Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2023 (Date of Event Which Requires Filing of this Statement) Check

February 14, 2024 SC 13G/A

ROOT / Root, Inc. / Timm Alexander E. - SC 13G/A Passive Investment

SC 13G/A 1 timm13ga-2023.htm SC 13G/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3)* Root, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 77664L207 (CUSIP Number) December 31, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to w

February 14, 2024 SC 13G/A

ROOT / Root, Inc. / DRIVE CAPITAL OVERDRIVE FUND I, L.P. - SC 13G/A Passive Investment

SC 13G/A 1 tm246208d1sc13ga.htm SC 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. 2)* Root, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 77664L207 (CUSIP Number) December 3

February 14, 2024 SC 13G

ROOT / Root, Inc. / SVB Capital Management, LLC - SC 13G Passive Investment

SC 13G 1 d706756dsc13g.htm SC 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2023 (Date of Event Which Requires Filing of this Statement) Check the app

November 15, 2023 SC 13D/A

ROOT / Root Inc - Class A / CARVANA GROUP, LLC - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 5) * Root, Inc. (Name of Issuer) Class A common stock, $0.0001 par value per share (Title of Class of Securities) 77664L108 (CUSIP Number) Ernest Garcia III President, Chief Executive Officer and Chairman 300 E. Rio Salado Parkway Tempe, Arizona 85281 (602

November 15, 2023 SC 13D/A

ROOT / Root Inc - Class A / Silver Lake Group, L.L.C. - SC 13D/A Activist Investment

SC 13D/A 1 d718579dsc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* Root, Inc. (Name of Issuer) Class A Common Stock, $0.0001 par value per share (Title of Class of Securities) 77664L207 (CUSIP Number) Andrew J. Schader, Esq. Silver Lake 55 Hudson Yards 550 West 34th Street, 40th Fl

November 1, 2023 EX-10.2

Performance-Based RSU Award Grant Notice

Exhibit 10.2 ROOT, INC. PERFORMANCE-BASED RSU AWARD GRANT NOTICE (2020 EQUITY INCENTIVE PLAN) Root, Inc. (the “Company”) has awarded to you (the “Participant”) the number of restricted stock units specified and on the terms set forth below in consideration of your services (the “RSU Award”). Your RSU Award is subject to all of the terms and conditions as set forth herein and in the Company’s 2020

November 1, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 1, 2023 ROOT, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 1, 2023 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number

November 1, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT,

November 1, 2023 EX-99.1

Gross accident period loss ratio

Q3 2023 Shareholder Letter Letter to Shareholders: Q3 2023 Key quarterly metrics: 2 Letter to Shareholders: Q3 2023 Dear Root Shareholders: We delivered a strong quarter, more than doubling our new writings quarter over quarter while maintaining our superior loss ratio.

October 26, 2023 EX-10.1

Root, Inc. Non-Employee Director Compensation Policy adopted October 23, 2023

Exhibit 10.1 Root, Inc. Non-Employee Director Compensation Policy Adopted October 23, 2023, with effect as of August 16, 2023 Each member of the Board of Directors (the “Board”) of Root, Inc. (the “Company”) who is not an employee of the Company (each, a “Non-Employee Director”) will receive the compensation described in this Non-Employee Director Compensation Policy (this “Director Compensation P

October 26, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 26, 2023 ROOT, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 26, 2023 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number

September 1, 2023 SC 13D/A

ROOT / Root Inc - Class A / CARVANA GROUP, LLC - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 4) * Root, Inc. (Name of Issuer) Class A common stock, $0.0001 par value per share (Title of Class of Securities) 77664L108 (CUSIP Number) Ernest Garcia III President, Chief Executive Officer and Chairman 300 E. Rio Salado Parkway Tempe, Arizona 85281 (602

August 11, 2023 EX-10.1

Executive Retention Agreement between Matt Bonakdarpour and Root, Inc. dated August 9, 2023

Exhibit 10.1 ROOT, INC. EXECUTIVE RETENTION AGREEMENT Dear Matt: The Compensation Committee recently approved a cash payment to you in the amount of $750,000.00. You will be required to repay all or a portion of the cash payment should you resign without Good Reason (as defined below) or be terminated for Cause (as defined below) on or prior to August 9, 2025. Accordingly, this agreement (this “Ag

August 11, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 8, 2023 ROOT, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 8, 2023 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

August 7, 2023 SC 13D/A

ROOT / Root Inc - Class A / CARVANA GROUP, LLC - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 3) * Root, Inc. (Name of Issuer) Class A common stock, $0.0001 par value per share (Title of Class of Securities) 77664L108 (CUSIP Number) Ernest Garcia III President, Chief Executive Officer and Chairman 300 E. Rio Salado Parkway Tempe, Arizona 85281 (602

August 2, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 2, 2023 ROOT, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 2, 2023 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

August 2, 2023 EX-10.1

Non-Employee Director Compensation Policy

Exhibit 10.1 Root, Inc. Non-Employee Director Compensation Policy Adopted: June 5, 2023 Each member of the Board of Directors (the “Board”) of Root, Inc. (the “Company”) who is not an employee of the Company (each, a “Non-Employee Director”) will receive the compensation described in this Non-Employee Director Compensation Policy (this “Director Compensation Policy”) for his or her Board service,

August 2, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

August 2, 2023 EX-99.1

Gross accident period loss ratio

Q2 2023 Shareholder Letter Letter to Shareholders: Q2 2023 Key quarterly metrics: 2 Letter to Shareholders: Q2 2023 Dear Root Shareholders: In Q2 2023, we saw continued momentum in our bottom line and returned to growing our customer base.

June 9, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 6, 2023 ROOT, INC. (Exact na

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 6, 2023 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

May 30, 2023 S-8

As filed with the Securities and Exchange Commission on May 30, 2023

As filed with the Securities and Exchange Commission on May 30, 2023 Registration No.

May 30, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Root, Inc (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity 2020 Equity Incentive Plan Class A Common Stock, par value $0.

May 15, 2023 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 12, 2023 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

May 15, 2023 EX-99.1

Root Promotes Seasoned Leaders from Within and Boosts Growth Efforts with New Business Development Leader Megan Binkley is promoted to Chief Financial Officer, Jon Allison is promoted to Chief Administrative Officer, and former president of ForeverCa

Root Promotes Seasoned Leaders from Within and Boosts Growth Efforts with New Business Development Leader Megan Binkley is promoted to Chief Financial Officer, Jon Allison is promoted to Chief Administrative Officer, and former president of ForeverCar, Jason Shapiro, joins the Root team to lead Business Development.

May 3, 2023 EX-10.3

Retention Bonus Agreement between Megan Binkley and Root, Inc.

Exhibit 10.3 November 16, 2022 RE: Retention Bonus Agreement Dear Megan, We are pleased to offer you this Retention Bonus Agreement (“Agreement”) to encourage your continued employment with Root Inc. or one of its subsidiaries (collectively, “the Company”). This Agreement does not modify the terms of your employment, or any agreement relating to confidentiality, trade secrets, and non-competition/

May 3, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

May 3, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 3, 2023 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (IR

May 3, 2023 EX-99.1

Gross accident period loss ratio

Q1 2023 Shareholder Letter Letter to Shareholders: Q1 2023 Key quarterly metrics: 2 Letter to Shareholders: Q1 2023 Dear Root Shareholders: In Q1 2023, we continued to drive the company toward profitability while accelerating new writings: •Recognized a 69% gross accident period loss ratio, a 13 point improvement year-over-year.

April 27, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION 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)

April 27, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION 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)

March 1, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 1, 2023 ROOT, INC. (Exact n

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 1, 2023 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (

March 1, 2023 EX-10.1

Executive Employment Agreement with Megan Binkley

EXECUTIVE EMPLOYMENT AGREEMENT THIS EXECUTIVE EMPLOYMENT AGREEMENT (this “Agreement”) is made as of August 19, 2022 (the “Effective Date”), between Caret Holdings, Inc, a Delaware corporation (and collectively with its parents, subsidiaries, and other corporate affiliates, and its or their successors or assigns (the “Company”), and Megan Binkley (“Executive”).

February 22, 2023 EX-99.1

Gross accident period loss ratio

Q4 2022 Shareholder Letter Letter to Shareholders: FY 2022 Key annual metrics 2 Letter to Shareholders: FY 2022 Dear Root Shareholders In 2022, we made substantial progress on our most important objectives: •Finished 2022 with a Q4 gross accident period loss ratio of 77%, down from 94% in Q4 2021, by leveraging our technology platforms to identify and rapidly respond to rising inflation, while the auto insurance industry has been experiencing an overall increase.

February 22, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 22, 2023 ROOT, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 22, 2023 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

February 22, 2023 EX-4.2

Description of Securities

Exhibit 4.2 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 Root, Inc. had one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”): our Class A common stock, $0.0001 par value per share (“Class A Common Stock”). References herein to the terms “we,” “our” and “us”

February 22, 2023 EX-3.3

Amended and Restated Bylaws of Root, Inc.

Exhibit 3.3 AMENDED AND RESTATED BYLAWS OF ROOT, INC. (A DELAWARE CORPORATION) ARTICLE I OFFICES Section 1.Registered Office. The registered office of the corporation in the State of Delaware shall be as set forth in the Certificate of Incorporation. Section 2.Other Offices. The corporation shall also have and maintain an office or principal place of business at such place as may be fixed by the B

February 22, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d)OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission file number 001-39658 ROOT, INC. (Exact

February 22, 2023 EX-10.34

Separation and Transition Agreement dated February 20, 2023, between Daniel Rosenthal and Root, Inc.

Exhibit 10.34 Separation and Transition Agreement This Separation and Transition Agreement (the “Transition Agreement”) is made and entered into by and between Root, Inc. (“Root” or the “Company”) and Daniel Rosenthal, an individual (“Executive”). Recitals WHEREAS, Executive has been employed by the Company on an at-will basis as Chief Financial Officer (“CFO”) and Chief Revenue & Operations Offic

February 14, 2023 SC 13G/A

ROOT / Root, Inc. Class A / Redpoint Omega II, L.P. - SC 13G/A Passive Investment

SC 13G/A 1 tm236543d1sc13ga.htm SC 13G/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2) * Root, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 77664L 10 8 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rule

February 14, 2023 SC 13G/A

US77664L2079 / Root, Inc., Class A / Timm Alexander E. - SC 13G/A Passive Investment

SC 13G/A 1 timm13ga-2022.htm SC 13G/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2)* Root, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 77664L207 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to w

February 14, 2023 SC 13G/A

ROOT / Root, Inc. Class A / HILLHOUSE CAPITAL ADVISORS, LTD. - ROOT, INC. Passive Investment

SC 13G/A 1 p23-0212sc13ga.htm ROOT, INC. SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 2)* Root, Inc. (Name of Issuer) Class A common stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of This Statement) Check the appropr

February 14, 2023 SC 13G/A

US77664L2079 / Root, Inc., Class A / Ribbit Capital IV, L.P. - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. 1)* Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 77664L207 (CUSIP Number) December 31, 2022 (Dat

February 10, 2023 SC 13G/A

US77664L2079 / Root, Inc., Class A / SVB FINANCIAL GROUP - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2)* Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 77664L 207 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the ru

February 9, 2023 SC 13G/A

US77664L2079 / Root, Inc., Class A / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 1)* Name of issuer: Root Inc./OH Class A Title of Class of Securities: Common Stock CUSIP Number: 77664L207 Date of Event Which Requires Filing of this Statement: December 30, 2022 Check the appropriate box to designate the rule pursuant to which this Schedule is filed:

December 30, 2022 8-K

Material Impairments, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 30, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

November 23, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 23, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

November 9, 2022 EX-10.1

First Amendment to 2020 Employee Stock Purchase Plan

Exhibit 10.1 FIRST AMENDMENT TO 2020 EMPLOYEE STOCK PURCHASE PLAN WHEREAS, the Board of Directors (the ?Board?) of Root, Inc. (the ?Company?) has adopted the 2020 Employee Stock Purchase Plan (the ?2020 ESPP?); and WHEREAS, the Board adopted the 2020 ESPP, effective as of October 18, 2020; and WHEREAS, on June 7, 2022, the Company?s stockholders approved a reverse stock split of the Company?s comm

November 9, 2022 EX-99.1

Gross accident period loss ratio

Q3 2022 Shareholder Letter Letter to Shareholders: Q3 2022 Key quarterly metrics: 2 Letter to Shareholders: Q3 2022 Dear Root Shareholders: Our third quarter shows clear progress on our strategy: accelerating new writings growth on our embedded platform while materially reducing our loss ratio year-over-year, bucking industry trend.

November 9, 2022 EX-10.2

First Amendment to 2020 Equity Incentive Plan

Exhibit 10.2 FIRST AMENDMENT TO 2020 EQUITY INCENTIVE PLAN WHEREAS, the Board of Directors (the ?Board?) of Root, Inc. (the ?Company?) has adopted the 2020 Equity Incentive Plan (the ?2020 Plan?) for the benefit of the 2020 Plan participants and to provide incentives to attract, retain and motivate eligible persons whose present and potential contributions are important to the success of the Compa

November 9, 2022 EX-10.3

First Amendment to 2015 Amended and Restated Equity Incentive Plan

Exhibit 10.3 FIRST AMENDMENT TO AMENDED AND RESTATED 2015 EQUITY INCENTIVE PLAN WHEREAS, the Board of Directors (the ?Board?) of Root, Inc. (the ?Company?) has adopted the Amended and Restated 2015 Equity Incentive Plan (the ?2015 Plan?) for the benefit of the 2015 Plan participants and to provide incentives to attract, retain and motivate eligible persons whose present and potential contributions

November 9, 2022 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 9, 2022 ROOT, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 9, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number

November 9, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT,

September 6, 2022 SC 13D/A

ROOT / Root, Inc. Class A / CARVANA GROUP, LLC - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 2) * Root, Inc. (Name of Issuer) Class A common stock, $0.0001 par value per share (Title of Class of Securities) 77664L108 (CUSIP Number) Ernest Garcia III President, Chief Executive Officer and Chairman 1930 W. Rio Salado Parkway Tempe, Arizona 85281 (48

August 24, 2022 SC 13D/A

ROOT / Root, Inc. Class A / CARVANA GROUP, LLC - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 1) * Root, Inc. (Name of Issuer) Class A common stock, $0.0001 par value per share (Title of Class of Securities) 77664L108 (CUSIP Number) Ernest Garcia III President, Chief Executive Officer and Chairman 1930 W. Rio Salado Parkway Tempe, Arizona

August 15, 2022 EX-3.1

Certificate of Amendment to Amended and Restated Certificate of Incorporation of Root, Inc.

Exhibit 3.1 CERTIFICATE OF AMENDMENT TO AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF ROOT, INC. Root, Inc., a corporation organized and existing under the General Corporation Law of the State of Delaware (the ?Company?), hereby certifies as follows: FIRST: That the Board of Directors of the Company has duly adopted resolutions (i) authorizing the Company to execute and file with the Secret

August 15, 2022 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Material Modification to Rights of Security Holders, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 12, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

August 8, 2022 EX-10.3

First Amendment to Carvana Commercial Agreement, dated as of May 13, 2022

EX-10.3 3 a103firstamendmenttocommer.htm EX-10.3 Exhibit 10.3 FIRST AMENDMENT TO THE PARTIES’ COMMERCIAL AGREEMENT This First Amendment to the Commercial Agreement (“Amendment”) is entered into and effective this 13th day of May, 2022 (the “Effective Date”), by and between Caret Holdings, Inc. (“Company”), Carvana, LLC (“Dealer”), Carvana Insurance Services, LLC (“CIS”), and Carvana Group, LLC (“P

August 8, 2022 EX-99.1

Gross accident period loss ratio

Q2 2022 Shareholder Letter Letter to Shareholders: Q2 2022 Key quarterly metrics: 2 Letter to Shareholders: Q2 2022 Dear Root Shareholders: The last 12 months have been one of the most difficult periods for auto insurers in decades.

August 8, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

August 8, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 8, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

August 8, 2022 EX-10.2

Executive Employment Agreement with Matt Bonakdarpour

Exhibit 10.2 EXECUTIVE EMPLOYMENT AGREEMENT THIS EXECUTIVE EMPLOYMENT AGREEMENT (this ?Agreement?) is made as of December 2, 2021, (the ?Effective Date?), between Caret Holdings, Inc, a Delaware corporation (and collectively with its parents, subsidiaries, and other corporate affiliates, and its or their successors or assigns (the ?Company?), and Matt Bonakdarpour (?Executive?). The Company and Ex

July 5, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 1, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

June 10, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 7, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

May 13, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 9, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (IR

May 4, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

May 4, 2022 EX-10.9

Form of Root, Inc. Cash Incentive Agreement

Exhibit 10.9 INCENTIVE BONUS AGREEMENT This Cash Incentive Agreement (the ?Agreement?), dated as of April 1, 2022, is made and entered into by and between Root Inc. (the ?Company?) and (the ?Employee?) (collectively, the ?Parties?). WHEREAS, the Employee has chosen, in connection with the Company?s 2022 Long-Term Incentive Program (the ?Program?), to receive a portion of the Employee?s 2022 long-t

May 4, 2022 EX-10.1

Term Loan Agreement, dated as of January 26, 2022, by and among the Company, Caret Holdings, Inc., as borrower, the loan parties party thereto and Acquiom Agency Services LLC, as the administrative agent for the lenders party thereto

Exhibit 10.1 Execution Version TERM LOAN AGREEMENT dated as of January 26, 2022 by and among CARET HOLDINGS, INC., as Borrower ROOT, INC., as Holdings THE OTHER LOAN PARTIES FROM TIME TO TIME PARTY HERETO, THE LENDERS FROM TIME TO TIME PARTY HERETO and ACQUIOM AGENCY SERVICES LLC, as Administrative Agent TABLE OF CONTENTS ARTICLE I DEFINITIONS; CONSTRUCTION Page Section 1.1. Section 1.2. Section 1

April 28, 2022 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION 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)

April 28, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

DEFA14A 1 definitiveadditionalproxym.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION 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 t

April 27, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 27, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

April 27, 2022 EX-99.1

Gross accident period loss ratio Seasoned state loss ratio

EX-99.1 2 q12022shareholderletter.htm EX-99.1 Q1 2022 Shareholder Letter Letter to Shareholders: Q1 2022 Key quarterly metrics: 2 Letter to Shareholders: Q1 2022 Dear Shareholders: We took aggressive actions in the first quarter of 2022 to reposition and restructure the company so we can continue to weather one of the most difficult times we’ve seen as a young company and in the personal auto indu

April 15, 2022 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION 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)

April 13, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Root, Inc (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity 2020 Equity Incentive Plan Class A Common Stock, par value $0.

April 13, 2022 S-8

As filed with the Securities and Exchange Commission on April 13, 2022

As filed with the Securities and Exchange Commission on April 13, 2022 Registration No.

March 23, 2022 EX-99.1

Root Adds Insurance Strength to Leadership Team with New CFO Rob Bateman will join the insurtech as CFO as Dan Rosenthal fully transitions into his role as Chief Revenue and Operating Officer

Root Adds Insurance Strength to Leadership Team with New CFO Rob Bateman will join the insurtech as CFO as Dan Rosenthal fully transitions into his role as Chief Revenue and Operating Officer COLUMBUS, Ohio, March 22, 2022, (GLOBE NEWSWIRE) ? Root, Inc.

March 23, 2022 EX-10.1

Executive Employment Agreement with Robert Bateman

Exhibit 10.1 EXECUTIVE EMPLOYMENT AGREEMENT THIS EXECUTIVE EMPLOYMENT AGREEMENT (this ?Agreement?) is made as of April 11, 2022, (the ?Effective Date?), between Caret Holdings, Inc, a Delaware corporation (and collectively with its parents, subsidiaries, and other corporate affiliates, and its or their successors or assigns (the ?Company?), and Robert Bateman (?Executive?). The Company and Executi

March 23, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 18, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

March 1, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 28, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

February 25, 2022 8-K/A

Costs Associated with Exit or Disposal Activities

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A (Amendment #1) CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 20, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commi

February 23, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d)OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission file number 001-39658 ROOT, INC. (Exact

February 23, 2022 EX-10.4

Root Inc, Non-Employee Director Compensation Policy adopted February 17, 2022

Exhibit 10.4 Root, Inc. Non-Employee Director Compensation Policy Adopted: February 17, 2022 Each member of the Board of Directors (the ?Board?) of Root, Inc. (the ?Company?) who is not an employee of the Company (each, a ?Non-Employee Director?) will receive the compensation described in this Non-Employee Director Compensation Policy (this ?Director Compensation Policy?) for his or her Board serv

February 23, 2022 EX-10.5

Amendment to the Fifth Amended and Restated Investors’ Rights Agreement by and among Root, Inc. and certain of its stockholders, dated October 28, 2020

Exhibit 10.5 ROOT, INC. AMENDMENT TO THE FIFTH AMENDED AND RESTATED INVESTORS? RIGHTS AGREEMENT This Amendment to the Fifth Amended and Restated Investors? Rights Agreement, as amended (this ?Amendment?), is made as of October 28, 2020 by and between Root, Inc., a Delaware corporation (the ?Company?) and the Investors set forth on the signature pages hereto. Capitalized terms not herein defined sh

February 23, 2022 EX-10.30

Root, Inc. Executive Compensation Agreement

Exhibit 10.30 ROOT, INC. EXECUTIVE COMPENSATION LETTER AGREEMENT Dear Dan: The Compensation Committee recently approved a cash payment to you in the amount of $4,981,250.00 in light of your promotion to Chief Revenue and Operating Officer, effective September 17, 2021, while simultaneously continuing as the Chief Financial Officer, and your successful closing of the Carvana transaction in October

February 23, 2022 EX-99.1

ROOT, INC. AND SUBSIDIARIES CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE LOSS - UNAUDITED Three Months Ended December 31, Years Ended December 31, 2021 2020 2021 2020 (in millions, except per share data) Revenues: Net premiums ea

Q4 2021 Shareholder Letter Letter to Shareholders: FY 2021 Key annual metrics: 2 Letter to Shareholders: FY 2021 Dear Shareholders: 2021 was a challenging year for insurtechs and auto insurer capital market investors as inflationary pressures led to rapidly accelerating loss trends.

February 23, 2022 EX-10.3

Form of Executive Retention Award

Exhibit 10.3 [DATE] Dear , Congratulations! Because your contribution to Root?s future success is critical, you are being offered a one-time retention incentive. The elements of this incentive are as follows: ?a one-time cash payment in the amount of $ (less applicable withholdings and standard deductions) if you are employed with Root, in good standing, on December 1, 2022, to be paid in a lump s

February 23, 2022 EX-10.2

Executive Employment Agreement by and between Caret Holdings, Inc. and Hemal Shah, dated December 16, 2021

Exhibit 10.2 EXECUTIVE EMPLOYMENT AGREEMENT THIS EXECUTIVE EMPLOYMENT AGREEMENT (this ?Agreement?) is made as of December 16, 2021, (the ?Effective Date?), between Caret Holdings, Inc, a Delaware corporation (and collectively with its parents, subsidiaries, and other corporate affiliates, and its or their successors or assigns (the ?Company?), and Hemal Shah (?Executive?). The Company and Executiv

February 23, 2022 EX-10.22

Form of Director and Officer Indemnity Agreement

Exhibit 10.22 INDEMNIFICATION AGREEMENT THIS INDEMNIFCATION AGREEMENT (the ?Agreement?) is made and entered into as of [Effective Date] between Root, Inc., a Delaware corporation (the ?Company?), and [Name of Director] (?Indemnitee?). WITNESSETH THAT: WHEREAS, highly competent persons have become more reluctant to serve corporations as directors or in other capacities unless they are provided with

February 23, 2022 EX-4.2

Description of Securities

Exhibit 4.2 DESCRIPTION OF THE REGISTRANT?S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 Root, Inc. had one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended, or the Exchange Act: our Class A common stock, $0.0001 par value per share. References herein to the terms ?we,? ?our? and ?us? refer to Root, Inc. and i

February 23, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 23, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

February 23, 2022 EX-21.1

List of subsidiaries of Root, Inc.

Exhibit 21.1 Subsidiaries of Root, Inc. Name Jurisdiction Caret Holdings, Inc. Delaware Root Enterprise, LLC Delaware Root Insurance Agency, LLC Ohio Root Insurance Company Ohio Root Lone Star Insurance Agency, Inc. Texas Root Property & Casualty Insurance Company Delaware Root Reinsurance Company, Ltd. Cayman Islands Root Scout, LLC Delaware

February 23, 2022 EX-10.6

Root, Inc. Non-Employee Director Compensation Policy adopted February 12, 2021

EXHIBIT 10.6 Root, Inc. Non-Employee Director Compensation Policy Adopted: February 12, 2021 Each member of the Board of Directors (the ?Board?) of Root, Inc. (the ?Company?) who is not an employee of the Company (each, a ?Non-Employee Director?) will receive the compensation described in this Non-Employee Director Compensation Policy (this ?Director Compensation Policy?) for his or her Board serv

February 23, 2022 EX-10.27

First Amendment to Amended and Restated Offer Letter by and between Root, Inc. and Daniel Rosenthal, dated February 23, 2022

Exhibit 10.27 FIRST AMENDMENT TO LETTER AGREEMENT THIS FIRST AMENDMENT TO LETTER AGREEMENT is dated as of February 23, 2022 (this Amendment), by and between Root, Inc. (the ?Company?) and Daniel Rosenthal. WITNESSETH: WHEREAS, the Company and Mr. Rosenthal are parties to the certain letter agreement dated as of February 24, 2021 (the ?Agreement?); and WHEREAS, subject to the terms and conditions s

February 23, 2022 EX-10.26

First Amendment to Offer Letter by and between Root, Inc. and Alexander Timm, dated February 22, 2022

Exhibit 10.26 FIRST AMENDMENT TO LETTER AGREEMENT THIS FIRST AMENDMENT TO LETTER AGREEMENT is dated as of February 22, 2022 (this Amendment), by and between Root, Inc. (the ?Company?) and Alexander Timm. WITNESSETH: WHEREAS, the Company and Mr. Timm are parties to the certain letter agreement dated as of January 4, 2021 (the ?Agreement?); and WHEREAS, subject to the terms and conditions set forth

February 15, 2022 SC 13G/A

ROOT / Root, Inc. Class A / DRIVE CAPITAL OVERDRIVE FUND I, L.P. - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. 1)* Root, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Fil

February 14, 2022 SC 13G/A

ROOT / Root, Inc. Class A / Timm Alexander E. - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.

February 14, 2022 SC 13G/A

ROOT / Root, Inc. Class A / HILLHOUSE CAPITAL ADVISORS, LTD. Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* Root, Inc. (Name of Issuer) Class A common stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rule pursuant t

February 14, 2022 SC 13G/A

ROOT / Root, Inc. Class A / Manges Daniel - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.

February 14, 2022 SC 13G/A

ROOT / Root, Inc. Class A / STAD MARC - SC 13G/A Passive Investment

SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1) * Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designa

February 14, 2022 SC 13G/A

ROOT / Root, Inc. Class A / ANGLEPOINT ASSET MANAGEMENT, LTD. - ROOT, INC. Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* Root, Inc. (Name of Issuer) Class A common stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rule pursuant t

February 11, 2022 SC 13G/A

ROOT / Root, Inc. Class A / Redpoint Omega II, L.P. - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.

February 11, 2022 EX-99.1

JOINT FILING AGREEMENT

EXHIBIT 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1) promulgated under the Securities Exchange Act of 1934, the undersigned agree to the joint filing of a Statement on Schedule 13G (including any and all amendments thereto) with respect to the Class A Common Stock, par value $0.0001 per share, of Root, Inc. and further agree to the filing of this agreement as an Exhibit thereto.

February 11, 2022 EX-99.2

Item 7 Information

EXHIBIT 99.2 ITEM 7 INFORMATION The securities being reported on herein by SVB Financial Group, as a parent holding company, are owned by Capital Partners III, L.P. and Venture Overage Fund, L.P., Delaware limited partnerships, and may be deemed to be beneficially owned, by SVB Financial Group. SVB Financial Group is the managing member of SVB Capital Partners III, LLC, a Delaware limited liabilit

February 11, 2022 SC 13G/A

ROOT / Root, Inc. Class A / SVB FINANCIAL GROUP - SCHEDULE 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 77664L 108 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the ru

February 10, 2022 SC 13G

ROOT / Root, Inc. Class A / VANGUARD GROUP INC - SCHEDULE 13G Passive Investment

SC 13G 1 tv01809-rootincohclassa.htm SCHEDULE 13G SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 Name of issuer: Root Inc./OH Class A Title of Class of Securities: Common Stock CUSIP Number: 77664L108 Date of Event Which Requires Filing of this Statement: December 31, 2021 Check the appropriate box to designate the rule pursuant to

February 8, 2022 SC 13G/A

ROOT / Root, Inc. Class A / Scale Venture Partners V, L.P. - SC 13G/A Passive Investment

SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Root, Inc.. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 77664L108 (CUSIP Number) 12/31/2021 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rule pursuant to which this S

February 8, 2022 EX-99.A

JOINT FILING AGREEMENT

EXHIBIT A JOINT FILING AGREEMENT In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, the undersigned agree to the joint filing on behalf of each of them of a statement on Schedule 13G (including amendments thereto) with respect to the Common Stock of Root, Inc.

January 27, 2022 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 27, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number

January 27, 2022 EX-4.2

Form of Common Stock Purchase Warrant (Tranche 2)

Exhibit 4.2 FINAL FORM THIS WARRANT AND THE SECURITIES ISSUABLE UPON THE EXERCISE HEREOF HAVE NOT BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND APPLICABLE STATE SECURITIES LAWS, AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD

January 27, 2022 EX-10.3

Registration Rights Agreement, dated January 26, 2022, by and between the Company and the other parties thereto.

EX-10.3 6 d295910dex103.htm EX-10.3 Exhibit 10.3 EXECUTION VERSION REGISTRATION RIGHTS AGREEMENT THIS REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of January 26, 2022 (the “Effective Date”), is made and entered into by and between Root, Inc., (the “Company”) and the undersigned parties listed on the signature pages hereto under “Holders” (together with any holder(s) of a Warrant (as

January 27, 2022 EX-99.1

Root Announces Closing of New Term Loan Facility with BlackRock

EX-99.1 7 d295910dex991.htm EX-99.1 Exhibit 99.1 Root Announces Closing of New Term Loan Facility with BlackRock COLUMBUS, Ohio, January 26, 2022 (GLOBE NEWSWIRE) — Root, Inc. (NASDAQ: ROOT), the parent company of Root Insurance Company, announced the successful completion of a new term loan facility with BlackRock Financial Management Inc., on behalf of funds and accounts under its management, an

January 27, 2022 EX-10.1

Term Loan Agreement, dated January 26, 2022, by and among the Company, Caret Holdings, Inc., as borrower, the other loan parties party thereto, the lenders party thereto and Acquiom Agency Services LLC, as the administrative agent for the lenders party thereto.

EX-10.1 4 d295910dex101.htm EX-10.1 Exhibit 10.1 Execution Version TERM LOAN AGREEMENT dated as of January 26, 2022 by and among CARET HOLDINGS, INC., as Borrower ROOT, INC., as Holdings THE OTHER LOAN PARTIES FROM TIME TO TIME PARTY HERETO, THE LENDERS FROM TIME TO TIME PARTY HERETO and ACQUIOM AGENCY SERVICES LLC, as Administrative Agent TABLE OF CONTENTS Page ARTICLE I DEFINITIONS; CONSTRUCTION

January 27, 2022 EX-10.2

Board Observation Side Letter, dated January 26, 2022, by and between the Company and GCO II Aggregator 2 L.P.

EX-10.2 5 d295910dex102.htm EX-10.2 Exhibit 10.2 ROOT, INC. 80 E. Rich Street, Suite 500 Columbus, OH 43215 January 26, 2022 Ladies and Gentlemen: Reference is made to that certain Term Loan Agreement, dated as of the date hereof (as amended, restated, amended and restated, supplemented or otherwise modified from time to time, the “Credit Agreement”), by and among Root, Inc., a Delaware corporatio

January 27, 2022 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 26, 2022 ROOT, INC. (Exact name of registrant as specified in its charter) Delaware 001-39658 84-2717903 (State or other jurisdiction of incorporation or organization) (Commis

January 27, 2022 EX-4.1

Form of Common Stock Purchase Warrant (Tranche 1), dated January 26, 2022

EX-4.1 Exhibit 4.1 FINAL FORM THIS WARRANT AND THE SECURITIES ISSUABLE UPON THE EXERCISE HEREOF HAVE NOT BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND APPLICABLE STATE SECURITIES LAWS, AND, ACCORDINGLY, MAY NOT BE OFFERED O

January 20, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Costs Associated with Exit or Disposal Activities

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 20, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number

January 20, 2022 EX-99.1

A Letter from Alex Timm, Co-Founder and CEO, Root, Inc.

EX-99.1 2 aletterfromalextimmco-foun.htm EX-99.1 A Letter from Alex Timm, Co-Founder and CEO, Root, Inc. Today, at our all-company meeting, I announced an organizational realignment that will drive efficiency and increased focus on Root’s strategic priorities. The most difficult part of this realignment is that we will say goodbye to approximately 330 team members throughout the business. As the p

January 6, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 1, 2022 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

November 19, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 18, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

November 10, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT,

November 10, 2021 EX-10.5

Third Amendment to Note Purchase Agreement, dated August 11, 2021, by and among Root, Inc., Caret Holdings, Inc., Wilmington Trust, National Association, and the noteholders from time to time party thereto

EX-10.5 2 a105root-thirdamendmentexe.htm EX-10.5 Exhibit 10.5 Execution Version THIRD AMENDMENT TO NOTE PURCHASE AGREEMENT THIS THIRD AMENDMENT TO NOTE PURCHASE AGREEMENT is dated as of August 11, 2021 (this “Amendment”), by and among CARET HOLDINGS, INC. (f/k/a Root, Inc.), a Delaware corporation (the “Issuer”), ROOT, INC. (f/k/a Root Stockholdings, Inc.), a Delaware corporation (“Holdings”), eac

November 10, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 10, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

November 10, 2021 EX-99.1

Key quarterly metrics: Gross written premium ($M) $119.6 $164.6 $204.6 3Q 2019 3Q 2020 3Q 2021 Gross earned premium ($M) $99.9 $154.4 $189.4 3Q 2019 3Q 2020 3Q 2021 Gross accident period loss ratio 100.3% 79.6% 91.3% 3Q 2019 3Q 2020 3Q 2021 Gross LAE

EX-99.1 2 rootshareholderletterq3-.htm EX-99.1 Key quarterly metrics: Gross written premium ($M) $119.6 $164.6 $204.6 3Q 2019 3Q 2020 3Q 2021 Gross earned premium ($M) $99.9 $154.4 $189.4 3Q 2019 3Q 2020 3Q 2021 Gross accident period loss ratio 100.3% 79.6% 91.3% 3Q 2019 3Q 2020 3Q 2021 Gross LAE ratio 12.7% 9.9% 10.6% 3Q 2019 3Q 2020 3Q 2021 Gross profit ($M) $(36.5) $0.7 $(16.1) 3Q 2019 3Q 2020

October 20, 2021 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 20, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number

October 12, 2021 SC 13D

ROOT / Root, Inc. Class A / CARVANA GROUP, LLC - SC 13D Activist Investment

SC 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. ) * Root, Inc. (Name of Issuer) Class A common stock, $0.0001 par value per share (Title of Class of Securities) 77664L108 (CUSIP Number) Ernest Garcia III President, Chief Executive Officer and Chairman 1930 W. Rio Salado Parkway Tempe, Arizona 85281

October 12, 2021 SC 13G

ROOT / Root, Inc. Class A / Schusterman Interests, LLC - SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Class A common stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) October 6, 2021 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule p

October 12, 2021 EX-99.1

JOINT FILING AGREEMENT

EX-99.1 Exhibit 1 JOINT FILING AGREEMENT This will confirm the agreement by and among the undersigned that the Schedule 13D filed with the Securities and Exchange Commission on or about the date hereof with respect to the beneficial ownership by the undersigned of the shares of Series A Convertible Preferred Stock, par value $0.0001 per share (“Preferred Stock”), of Root, Inc., is being filed, and

October 1, 2021 EX-4.1

Common Stock Purchase Warrants, dated as of October 1, 2021, by and between Root, Inc. and Carvana Group, LLC

Exhibit 4.1 THIS WARRANT AND THE SECURITIES ISSUABLE UPON THE EXERCISE HEREOF HAVE NOT BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND APPLICABLE STATE SECURITIES LAWS, AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURS

October 1, 2021 8-K

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 29, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numb

October 1, 2021 EX-10.3

First Amendment to Investment Agreement, dated as of September 29, 2021, by and between Root, Inc. and Carvana Group, LLC

Exhibit 10.3 EXECUTION VERSION FIRST AMENDMENT TO THE INVESTMENT AGREEMENT This FIRST AMENDMENT TO THE INVESTMENT AGREEMENT (this ?Amendment?), dated as of September 29, 2021, is entered into by and between Root, Inc., a Delaware corporation (the ?Company?), and Carvana Group, LLC, a Delaware limited liability company (the ?Purchaser?). The Company and the Purchaser are collectively referred to he

October 1, 2021 EX-3.1

Certificate of Designation of Series A Preferred Stock (incorporated by reference from Exhibit 3.1 to the Issuer’s Current Report on Form 8-K filed with the Commission on October 1, 2021).

Exhibit 3.1 CERTIFICATE OF DESIGNATIONS OF SERIES A CONVERTIBLE PREFERRED STOCK OF ROOT, INC. pursuant to Section 151 of the General Corporation Law of the State of Delaware Root, Inc., a Delaware corporation (the ?Company?), hereby certifies that: The Amended and Restated Certificate of Incorporation of the Company (the ?Certificate of Incorporation?) confers upon the Board of Directors of the Co

October 1, 2021 EX-10.1

Commercial Agreement, dated as of October 1, 2021

Exhibit 10.1 COMMERCIAL AGREEMENT THIS COMMERCIAL AGREEMENT (this ?Agreement?) is executed to be effective as of October 1, 2021 (the ?Effective Date?), by and between Caret Holdings, Inc., on behalf of itself, subsidiaries, and affiliates (the ?Company?), Carvana, LLC, an Arizona limited liability Company (?Dealer?), Carvana Insurance Services, LLC, an Arizona limited liability company (?CIS?), a

September 21, 2021 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 17, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numb

September 21, 2021 EX-99.1

Root, Inc. Announces Organizational Changes to Accelerate Growth of Corporate Initiatives Daniel Rosenthal will take on the role of Chief Revenue and Operating Officer in addition to his responsibilities as Chief Financial Officer

Press release Root, Inc. Announces Organizational Changes to Accelerate Growth of Corporate Initiatives Daniel Rosenthal will take on the role of Chief Revenue and Operating Officer in addition to his responsibilities as Chief Financial Officer COLUMBUS, OH ? Root, Inc. (NASDAQ: ROOT), a leading technology company powering insurance solutions and the parent company of Root Insurance, today announc

August 12, 2021 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 11, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

August 12, 2021 EX-10.1

Form of Root, Inc. 2020 Equity Incentive Plan Stock Option Grant Notice and Option Agreement

Exhibit 10.1 Root, Inc. Stock Option Grant Notice (2020 Equity Incentive Plan) Root, Inc. (the ?Company?), pursuant to its 2020 Equity Incentive Plan (the ?Plan?), has granted to you (?Optionholder?) an option to purchase the number of shares of the Common Stock set forth below (the ?Option?). Your Option is subject to all of the terms and conditions as set forth herein and in the Plan and the Sto

August 12, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

August 12, 2021 EX-10

Investment Agreement, dated as of August 11, 2021, by and between Root, Inc. and Carvana Group, LLC

Exhibit 10.1 EXECUTION VERSION INVESTMENT AGREEMENT between ROOT, INC. as the Company, and CARVANA GROUP, LLC as the Purchaser, Dated as of August 11, 2021 TABLE OF CONTENTS 1. INVESTMENT 2 2. CLOSING 2 2.1 Closing Date 2 2.2 Issuance of Securities 2 2.3 Additional Rights 2 2.4 Payment of Purchase Price 3 2.5 Closing Actions and Deliveries 3 3. CONDITIONS TO CLOSING 3 3.1 Conditions to the Obligat

August 12, 2021 EX-99

Carvana and Root, Inc. Exclusively Partner to Develop Industry-First Integrated Auto Insurance Solutions for Carvana Customers

Exhibit 99.1 Carvana and Root, Inc. Exclusively Partner to Develop Industry-First Integrated Auto Insurance Solutions for Carvana Customers ? Carvana to invest approximately $126 million in leading insurtech Root, Inc. PHOENIX and COLUMBUS, August 11, 2021 ? Carvana (NYSE: CVNA), the leading e-commerce platform for buying and selling used cars, and Root, Inc. (NASDAQ: ROOT), the parent company of

August 12, 2021 EX-3.2

Amended and Restated Bylaws of Root, Inc.

EXHIBIT 3.2 AMENDED AND RESTATED BYLAWS OF ROOT, INC. (A DELAWARE CORPORATION) ARTICLE I OFFICES Section 1.Registered Office. The registered office of the corporation in the State of Delaware shall be as set forth in the Certificate of Incorporation. Section 2.Other Offices. The corporation shall also have and maintain an office or principal place of business at such place as may be fixed by the B

August 12, 2021 EX-10.2

, Inc. and Anirban Kundu, dated June 21, 2021

Exhibit 10.2 EXECUTIVE EMPLOYMENT AGREEMENT THIS EXECUTIVE EMPLOYMENT AGREEMENT (this ?Agreement?) is made as of June 21, 2021 (the ?Effective Date?), between Caret Holdings, Inc, a Delaware corporation (and collectively with its parents, subsidiaries, and other corporate affiliates, and its or their successors or assigns (the ?Company?), and Anirban Kundu (?Executive?). The Company and Executive

August 11, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 11, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number)

August 11, 2021 EX-99.1

Q1 2021 Letter to Shareholders: Q2 2021 2 Key quarterly metrics: Letter to Shareholders: Q2 2021 3 Dear shareholders: Through the second quarter of 2021, we continued to execute on our founding premise that machine learning and technology will fundam

Q1 2021 Letter to Shareholders: Q2 2021 2 Key quarterly metrics: Letter to Shareholders: Q2 2021 3 Dear shareholders: Through the second quarter of 2021, we continued to execute on our founding premise that machine learning and technology will fundamentally improve the insurance industry.

July 2, 2021 EX-10.1

isor Agreement with Daniel Manges, effective July 3, 2021

ADVISOR AGREEMENT This Advisor Agreement (the ?Agreement?) is entered into between Root, Inc.

July 2, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 1, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

June 11, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 8, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

June 7, 2021 EX-99.1

Root, Inc. Bolsters Leadership Team with New Hires

Root, Inc. Bolsters Leadership Team with New Hires Root Inc., the parent company of Root Insurance Company, announces key new hires as company extends its technical leadership and launches into its next chapter of growth Root, Inc. (NASDAQ: ROOT), a leading AI technology provider for insurance and parent company of Root Insurance Company, today announced key additions to the executive leadership t

June 7, 2021 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 7, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (I

May 13, 2021 S-8

As filed with the Securities and Exchange Commission on May 13, 2021

As filed with the Securities and Exchange Commission on May 13, 2021 Registration No.

May 13, 2021 EX-99.2

Root, Inc. 2020 Employee Stock Purchase Plan.

EXHIBIT 99.2 Root, Inc. 2020 Employee Stock Purchase Plan Adopted by the Board of Directors: October 18, 2020 Approved by the Stockholders: October 19, 2020 IPO Date: October 28, 2020 1.General; Purpose. (a)The Plan provides a means by which Eligible Employees of the Company and certain designated Related Corporations may be given an opportunity to purchase shares of Class A Common Stock. The Plan

May 11, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 5, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (IR

May 6, 2021 EX-3.2

Amended and Restated Bylaws of Root, Inc.

EXHIBIT 3.2 AMENDED AND RESTATED BYLAWS OF ROOT, INC. (A DELAWARE CORPORATION) ARTICLE I OFFICES Section 1.Registered Office. The registered office of the corporation in the State of Delaware shall be as set forth in the Certificate of Incorporation. Section 2.Other Offices. The corporation shall also have and maintain an office or principal place of business at such place as may be fixed by the B

May 6, 2021 EX-10.2

Form of Root, Inc. 2020 Equity Incentive Plan RSU Award Grant Notice and Award Agreement

EXHIBIT 10.2 Root, Inc. RSU Award Grant Notice (2020 Equity Incentive Plan) Root, Inc. (the ?Company?) has awarded to you (the ?Participant?) the number of restricted stock units specified and on the terms set forth below in consideration of your services (the ?RSU Award?). Your RSU Award is subject to all of the terms and conditions as set forth herein and in the Company?s 2020 Equity Incentive P

May 6, 2021 EX-10.1

Root, Inc. Non-Employee Director Compensation Policy

EXHIBIT 10.1 Root, Inc. Non-Employee Director Compensation Policy Adopted: March 6, 2021 Each member of the Board of Directors (the ?Board?) of Root, Inc. (the ?Company?) who is not an employee of the Company (each, a ?Non-Employee Director?) will receive the compensation described in this Non-Employee Director Compensation Policy (this ?Director Compensation Policy?) for his or her Board service,

May 6, 2021 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number: 001-39658 ROOT, INC.

May 5, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 5, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number) (IR

May 5, 2021 EX-99.1

Q1 2021 Letter to Shareholders: Q1 2021 2 Key quarterly metrics: Letter to Shareholders: Q1 2021 3 Dear Shareholders: We are very pleased to report and comment on Root’s strong financial and operating performance in Q1 2021. In Q1, our first full qua

Q1 2021 Letter to Shareholders: Q1 2021 2 Key quarterly metrics: Letter to Shareholders: Q1 2021 3 Dear Shareholders: We are very pleased to report and comment on Root?s strong financial and operating performance in Q1 2021.

May 4, 2021 SC 13G/A

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Root, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) (CUSIP Number) December 31, 2020 (Date of Event

SC 13G/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No.

April 29, 2021 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION 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)) De

April 29, 2021 DEF 14A

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION 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)) ?

March 4, 2021 EX-10.16

Offer Letter by and between Root, Inc. and Alexander Timm, dated

Exhibit 10.16 November 1, 2020 Alexander Timm Re: Employment Terms Dear Alex: You are currently employed with Root, Inc. (the ?Company?). This letter agreement confirms the terms and conditions of your employment (the ?Agreement?). As of your execution of this Agreement, you acknowledge and agree that you are no longer eligible for nor entitled to any further compensation or benefits under the ter

March 4, 2021 EX-10.13

Amended and Restated Term Loan Agreement by and among Root, Inc., Caret Holdings, Inc., SunTrust Bank, and the lenders from time to time party thereto, dated November 25, 2019, as amended.

Execution Version AMENDED AND RESTATED TERM LOAN AGREEMENT dated as of November 25, 2019 by and among ROOT, INC.

March 4, 2021 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d)OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission file number 001-39658 ROOT, INC. (Exact

March 4, 2021 EX-10.17

Amended and Restated Offer Letter by and between Root, Inc. and Daniel Rosenthal, dated

Exhibit 10.17 February 24,2021 Daniel Rosenthal 9101 Burning Tree Road Bethesda MD 20817 Re: Employment Terms Dear Dan: You are currently employed with Root, Inc. (the ?Company?). This letter agreement confirms the terms and conditions of your employment (the ?Agreement?). As of your execution of this Agreement, you acknowledge and agree that you are no longer eligible for nor entitled to any furt

March 4, 2021 EX-21.1

List of subsidiaries of Root, Inc.

Exhibit 21.1 Subsidiaries of Root, Inc. Name Jurisdiction Caret Holdings, Inc. Delaware Root Enterprise, LLC Delaware Root Insurance Company Ohio Root Insurance Agency, LLC Ohio Root Reinsurance Company, Ltd. Cayman Islands Buzzwords Labs Inc. Delaware Root Property & Casualty Insurance Company Delaware

March 4, 2021 EX-10.7

Form of Notice of Stock Option Exercise and Stock Option Exercise Agreement under the Amended and Restated 2015 Equity Incentive Plan.

Exhibit 10.7 ROOT, INC. NOTICE OF EXERCISE Root, Inc. 80 E. Rich Street, Ste. 500 Columbus, Ohio 43215 Ladies and Gentlemen: 1.Option. The person named below (the ?Purchaser?) was granted an option (the ?Option?) to purchase shares of Common Stock of Root, Inc., a Delaware corporation (the ?Company?) pursuant to the Company?s 2015 Equity Incentive Plan (the ?Plan?), by Notice of Stock Option Grant

March 4, 2021 EX-10.18

Offer Letter by and between Root, Inc. and Daniel Manges, dated

Exhibit 10.18 February 24, 2021 Daniel Manges 1185 Bluffway Dr. Columbus, OH 43235 Re: Employment Terms Dear Daniel: You are currently employed with Root, Inc. (the ?Company?). This letter agreement confirms the terms and conditions of your employment (the ?Agreement?). As of your execution of this Agreement, you acknowledge and agree that you are no longer eligible for nor entitled to any further

March 4, 2021 EX-4.2

Description of Securities

Exhibit 4.2 DESCRIPTION OF THE REGISTRANT?S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 As of December 31, 2020, Root, Inc. had one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended, or the Exchange Act: our Class A common stock, $0.0001 par value per share. References herein to the terms ?we,? ?our? and ?us?

February 25, 2021 EX-99.1

/ Letter to Shareholders: FY 2020 2 Key annual metrics: Direct Contribution ($m) Letter to Shareholders: FY 2020 3 Dear Shareholders, 2020 was an unprecedented year by any measure. The first global pandemic in over 100 years profoundly disrupted the

root4q2020shareholderlet / Letter to Shareholders: FY 2020 2 Key annual metrics: Direct Contribution ($m) Letter to Shareholders: FY 2020 3 Dear Shareholders, 2020 was an unprecedented year by any measure.

February 25, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 25, 2021 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

February 16, 2021 SC 13G

Root, Inc.

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Class A common stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rule pursuant to w

February 16, 2021 SC 13G

Root, Inc.

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Class A common stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rule pursuant to w

February 16, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. __)*

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. )* Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2020 (Date

February 16, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) * Root, Inc.

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No.

February 12, 2021 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securiti

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 77664L 108 (CUSIP Number) February 12, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rul

February 12, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. __)*

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. )* Root, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Fili

February 12, 2021 EX-99.2

ITEM 7 INFORMATION

EX-99.2 3 rootsc13-gexhibit992.htm EXHIBIT 99.2 EXHIBIT 99.2 ITEM 7 INFORMATION The securities being reported on herein by SVB Financial Group, as a parent holding company, are owned by Capital Partners III, L.P. and Venture Overage Fund, L.P., Delaware limited partnerships, and may be deemed to be beneficially owned, by SVB Financial Group. SVB Financial Group is the general partner of Capital Pa

February 12, 2021 EX-99.1

JOINT FILING AGREEMENT

EXHIBIT 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1) promulgated under the Securities Exchange Act of 1934, the undersigned agree to the joint filing of a Statement on Schedule 13G (including any and all amendments thereto) with respect to the Class A Common Stock, par value $0.0001 per share, of Root, Inc. and further agree to the filing of this agreement as an Exhibit thereto.

February 11, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. __)* Root, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) (CUSIP Number) December 31, 2020 (Date of Event

SC 13G 1 d129971dsc13g.htm SC 13G SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 77664L108 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which

February 11, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) (CUSIP Number) December 31, 2020 (Date of Event W

SC 13G SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No.

February 10, 2021 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) (CUSIP Number) (Date of E

SC 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )* Root, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 77664L108 (CUSIP Number) 12/31/2020 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rule pursuant to which this Sched

February 10, 2021 EX-99.A

JOINT FILING AGREEMENT

EX-A EXHIBIT A JOINT FILING AGREEMENT In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, the undersigned agree to the joint filing on behalf of each of them of a statement on Schedule 13G (including amendments thereto) with respect to the Common Stock of Root, Inc.

December 2, 2020 EX-10.1

Root, Inc. 2020 Equity Incentive Plan.

Root, Inc. 2020 Equity Incentive Plan Adopted by the Board of Directors: October 18, 2020 Approved by the Stockholders: October 19, 2020 1.General. (a)Successor to and Continuation of Prior Plan. The Plan is the successor to and continuation of the Prior Plan. As of the Effective Date, (i) no additional awards may be granted under the Prior Plan; (ii) the Prior Plan’s Available Reserve (plus any R

December 2, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period fromto Commission File Number:001-39658 ROOT, I

December 1, 2020 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 1, 2020 ROOT, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 1, 2020 ROOT, INC. (Exact name of Registrant as Specified in Its Charter) Delaware 001-39658 84-2717903 (State or Other Jurisdiction of Incorporation) (Commission File Number

Fintel data has been cited in the following publications:
Daily Mail Fox Business Business Insider Wall Street Journal The Washington Post Bloomberg Financial Times Globe and Mail
NASDAQ.com Reuters The Guardian Associated Press FactCheck.org Snopes Politifact
Federal Register The Intercept Forbes Fortune Magazine TheStreet Time Magazine Canadian Broadcasting Corporation International Business Times
Cambridge University Press Investopedia MarketWatch NY Daily News Entrepreneur Newsweek Barron's El Economista