2025 Proxy Statement

Kemper is improving the world of insurance by providing affordable and personalized auto and life solutions for individuals, families and businesses

CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

This Notice of Annual Meeting of Shareholders and Proxy Statement contains forward-looking statements, within the meaning of the Private Securities Litigation Reform Act of 1995, that involve risks and uncertainties. Forward-looking statements provide current expectations of future events based on certain assumptions and include any statement that does not directly relate to any historical or current fact. Forward-looking statements also can be identified by "believe(s)," "goal(s)," "target(s)," "estimate(s)," "anticipate(s)," "forecast(s)," "project(s)," "plan(s)," "intend(s)," "expect(s)," "might," "may," "could" and other terms of similar meaning. Any or all forward-looking statements may tuout to be wrong, and, accordingly, Kemper cautions readers not to place undue reliance on such statements. Forward-looking statements involve a number of risks and uncertainties that are difficult to predict. These statements are not guarantees of future performance, and actual results could differ materially from those expressed or implied in the forward-looking statements. Forward-looking statements can be affected by inaccurate assumptions or by known or unknown risks and uncertainties that may be important in determining the Company's actual future results and financial condition. Information on potential factors that could affect Kemper's financial results is included from time to time in the "Risk Factors" and "Management's Discussion and Analysis of Financial Condition and Results of Operations" sections of the Company's public reports filed with the SEC, including the Company's Form 10-K for the fiscal year ended December 31, 2024. The Company assumes no obligation to update any forward-looking statements or information, which speak as of their respective dates.

Notice of 2025 Annual Meeting of Shareholders to be Held May 7, 2025

Voting Items

Board RecommendationPage Reference

1 2 3 4

Elect the nominees named in the attached Proxy Statement to the Board of Directors

FOR

4

all director nominees

Vote on an advisory proposal to approve the compensation of the Company's Named Executive Officers, as disclosed in this Proxy Statement

Vote on a proposal to approve the Company's Second Amended and Restated 2023 Omnibus Plan

Vote on an advisory proposal to ratify the selection of Deloitte & Touche LLP as the Company's independent registered public accounting firm for 2025

FORFORFOR

30 68 76

We will also consider and act upon such other business as may be properly brought before the meeting.

Your vote is important to us. To show our appreciation for your participation, The Kemper Foundation will make a $1 donation to the American Heart Association for every shareholder account that participates in connection with the 2025 Annual Meeting of Shareholders ("Annual Meeting").

The Board of Directors of Kemper has fixed March 13, 2025 as the record date ("Record Date") for determining shareholders entitled to receive this notice and to vote at the Annual Meeting or any adjournments or postponements of the meeting. Only shareholders of record at the close of business on the Record Date will be entitled to notice of, and to vote at, the

Annual Meeting.

If you wish to examine a list of registered shareholders as of March 13 during the 10-day period prior to the Annual Meeting date, please contact Investor Relations atinvestors@kemper.com.

By Order of the Board of Directors,

C. Thomas Evans, Jr.

Secretary

Chicago, Illinois March 26, 2025

How to Vote

Important Notice Regarding the Availability of Proxy Materials for the Annual Meeting of Shareholders to be held on May 7, 2025: The Company's 2025 Proxy Statement and 2024 Annual Report to Shareholders are available at proxyvote.com.

Regardless of whether you plan to attend the Annual Meeting, please vote your proxy as promptly as possible. You may vote by timely returning your signed and dated proxy card in the postage-paid envelope provided, or you may vote by telephone or through the Internet. Instructions are printed on your proxy card.

Table of Contents

010304

Notice of 2025 Annual Meeting ofShareholders to be Held May 7, 2025

Voting Roadmap

Proposal 1: Election of Directors

• 4Overview

• 5Director Nominees

• 6Key Characteristics Represented onthe Board

• 7Director Biographies

• 12 Board Composition

14

Corporate Governance

• 14 Board Leadership Structure

• 18 Board Effectiveness

• 19 Board Oversight

• 22 Investor Relations in 2024

• 22 Corporate Responsibility at Kemper

• 23 Communicating with our Board

• 23 Other Governance Matters

24 27 30

Director Compensation

24

2024 Annual Non-Employee Director Compensation Program

Executive Officers

Proposal 2: Advisory Vote to Approve the Compensation of the Company's Named Executive Officers

30 Overview

31

Executive Compensation

• 31 Human Resources & Compensation Committee Report

• 32 Human Resources & Compensation Committee Governance

• 33 Compensation Discussion & Analysis

• 50 Compensation Tables 2024

• 63 CEO Pay Ratio

• 63 Pay Versus Performance

68

Proposal 3: Vote to Approve the Second Amended and Restated Kemper Corporation 2023 Omnibus Plan

• 68 Overview and Reason for Proposal

• 69 Key Features of the Second A&R Plan

• 69 BuRate, Outstanding Equity Awards, and Overhang & Dilution

• 70 Summary Description of the Second A&R Plan

76

Proposal 4: Advisory Vote to Ratify the Selection of Deloitte & Touche LLP as the Company's Independent Registered Public Accounting Firm

76 Overview

77 Audit Fees and All Other Fees

77 Audit Committee Pre-Approval Policies and Procedures

77

Audit Committee Report

78

Beneficial Ownership of Common Stock

• 78 Security Ownership of Certain Beneficial Owners

• 79 Security Ownership of Directors and Executive Officers

• 79 Delinquent Section 16(a) Reports

80

Frequently Asked Questions about the Annual Meeting and Voting/ Incorporation by Reference

• 80 Proxy and Proxy Statement

• 80 Voting and Record Date

• 83 Shareholder Proposals, Nominations and Communications

• 84 Cost of Proxy Solicitation

• 85 Additional Information about Kemper and Householding Requests

• 85 Incorporation by Reference

86 87 88

Appendix A-1 - Reconciliation of GAAP and Non-GAAP Financial Measures

Appendix A-2 - Performance Metrics

Appendix B - Second Amended and Restated Kemper Corporation 2023 Omnibus Plan

Voting Roadmap

Election of the nominees named in this Proxy Statement to the Board of Directors

Shareholders are being asked to elect 10 directors named in this Proxy Statement.

The Board of Directors recommends that you vote "FOR" the Election of all ten Nominees for Director named in this Proxy Statement.

See Page4

See Page30

See Page68

See Page76

Election of Directors

Overview

Shareholders are being asked to elect the 10 director nominees named in this Proxy Statement. If elected, each nominee will serve for an annual term expiring at our 2026 Annual Meeting of Shareholders ("2026 Annual Meeting") or until the election of their successors, or as otherwise provided under the Company's Amended and Restated Bylaws ("Bylaws"). If any of the director nominees for election to the Board at the Annual Meeting named below ("Nominees")declines or is unable to serve as a director (neither of which is anticipated), the individuals designated as proxies on the proxy card reserve full discretion to vote for any or all other persons who may be nominated. A Nominee will be elected if the number of votes cast "FOR" exceeds the number of votes cast "AGAINST" his or her election.

Required Vote

Under the Company's Bylaws, if a quorum is present, each Nominee will be elected if the votes cast "FOR" such Nominee's election exceed the votes cast "AGAINST" such Nominee's election (i.e., by the affirmative vote of a majority of the votes cast). "Abstentions" and "broker non-votes" are not considered votes cast "FOR" or "AGAINST" the foregoing purpose and will have no effect on the election of Nominees. If a Nominee who is an incumbent director receives a greater number of votes "AGAINST" his or her election than votes "FOR" such election, the Company's Bylaws require that such director must promptly tender his or her resignation to the Board following certification of the vote.

Director Nominees

The following provides summary information about each director nominee.

Name and Primary Occupation

Current Committee MembershipAgeDirector SinceACGCHR&CCICRC

Teresa A. CanidaINDEPENDENTPrincipal and Portfolio Manager, Ceeto Capital Group, LLC

71

2018

C

George N. CochranINDEPENDENTFormer Chairman, Global Financial Institutions Group,

Macquarie Capital

70

2015

C

Jason N. GorevicINDEPENDENTFormer Chief Executive Officer, Teladoc Health, Inc.

53

2022

Lacy M. JohnsonINDEPENDENTPartner, Taft Stettinius & Hollister LLP

72

2016

Joseph P. Lacher, Jr.

President & Chief Executive Officer, Kemper Corporation

55

2015

Gerald LadermanCHAIRMAN, INDEPENDENT

Former Executive Vice President and Chief Financial Officer, United Airlines Holdings, Inc.

67

2020

C

Suzet M. McKinneyINDEPENDENT

Former Principal & Director of Life Sciences, Sterling Bay Company, LLC

52

2024

Alberto J. ParacchiniINDEPENDENT

Chief Executive Officer, President and Director of Byline Bank

54

2023

C

Stuart B. ParkerINDEPENDENTFormer President and

Chief Executive Officer, USAA

63

2020

Susan D. WhitingINDEPENDENT

Former Vice Chair, Nielsen Holdings plc

68

2017

C

ACAudit Committee

HR&CCHuman Resources and

Compensation CommitteeGCGovernance Committee

• ICInvestment Committee

• RCRisk Committee

Member Chair

Key Characteristics Represented on the Board

The Governance Committee considers and recommends candidates for the Board. Each of the individuals selected as a Nominee meets the standards for Board nominees as described below in theDirector Nomination Processsection beginning on page 12. The Governance Committee and the Board believe each Nominee has demonstrated the significant business achievements, ethical principles and commitment to serve the Company and its shareholders, and that the specific experience, qualifications, attributes and skills of each Nominee add to the collective ability of the Board to perform its duties and discharge its responsibilities with competence, professionalism and expertise.

Board Nominee Snapshot

Director Skills and Experience Matrix

Experience

Insurance Industry
Executive Experience
Risk Management
Investment Management
Accounting/Finance
Consumer-Focused Business
Human Capital
IT/Cyber
Corporate Governance
Corporate Responsibility
Regulatory/Policy
Business Development

Background

Independence
Tenure (years)	7	10	3	9	10	5	1	2	5	8
Age	71	70	53	72	55	67	52	54	63	68

Director Biographies

The following is a summary of the background and public-company directorships held by each Nominee over at least the past five years. Also included are specific factors particular to such Nominee that, combined with the generally applicable factors noted below, led the Board to conclude they should be selected as a Nominee for election to the Board at the Annual Meeting.

Teresa A. Canida

CURRENT ROLE

• •Principal and Portfolio Manager, Ceeto Capital Group, LLC, 2016-Present

• •Director, Kemper Corporation, 2018-Present

BACKGROUND & PAST EXPERIENCE

• •Chairperson, Taplin, Canida & Habacht LLC

• •President, Taplin, Canida & Habacht LLC

• •President, Managing Principal, and Chief Compliance Officer, Taplin, Canida & Habacht LLC

• •Director, Infinity Property and Casualty Corporation ("Infinity") (acquired by Kemper in 2018)

• •Member, Investment Advisory Council of the Florida State Board of Administration

Committees:Audit,

Investment (Chair)

REASONS FOR NOMINATION

Age: 71

Director since: 2018

Skills:

• •Insurance Industry

• •Executive Experience

• •Investment Management

• •Risk Management

• •Corporate Governance

  Ms. Canida is a highly successful leader in the investment management industry. She has extensive experience in portfolio management and has served in senior leadership roles in the industry as co-founder, principal and president of a multi-billion dollar investment advisory firm. Ms. Canida's extensive experience in investments, risk management and executive leadership provides Kemper with valuable insight in these areas. Ms. Canida has been recognized as a leader in the Latino/Hispanic business community and the Board values her extensive knowledge of the Company's Latino/Hispanic consumer base. Additionally, Ms. Canida brings important expertise of the specialty auto insurance business from her tenure on the Infinity Board of Directors.

• •Corporate Responsibility

• •Consumer-Focused Business

Ms. Canida serves as a member of the Investment Advisory Council of the Florida State Board of Administration.

George N. Cochran

CURRENT ROLE

• •Managing Partner, Cochran Booth & Co., 2014-Present

• •Director, Kemper Corporation, 2015-Present

BACKGROUND & PAST EXPERIENCE

• •Chairman, Global Financial Institutions Group, Macquarie Capital

• •Chairman, Fox-Pitt Kelton Cochran Caronia Waller (acquired by Macquarie Capital in 2009)

• •Co-founder, Cochran Caronia Waller

• •Managing Director and Insurance Industry Head, Coopers & Lybrand Securities, LLC

• •Investment Banker, Kidder, Peabody & Co.

Committees:HR&CC,

Risk (Chair)

REASONS FOR NOMINATION

Age: 70

Director since: 2015

Skills:

• •Insurance Industry

• •Executive Experience

• •Investment Management

  Mr. Cochran is an experienced financial and investment professional, serving in senior leadership positions at several investment banking and securities firms. His knowledge of the insurance industry, corporate transactions, and corporate finance is a significant benefit to the Board. With this experience and expertise, Mr. Cochran provides the Board with valuable insight on executive development, corporate transactions, risk management, corporate governance, and operational and strategic matters. Mr. Cochran's wide industry experience makes him a particularly effective leader of the Company's Risk Committee.

• •Risk Management

• •Corporate Governance

• •Business Development

The Board also values Mr. Cochran's commitment to boardroom excellence. He is a National Association of Corporate Directors ("NACD") Governance Fellow and Board Leadership Fellow, and has completed NACD's comprehensive program of study for directors and corporate governance professionals.

Jason N. Gorevic

CURRENT ROLE

• •Director, Kemper Corporation, 2022-Present

BACKGROUND & PAST EXPERIENCE

• •Chief Executive Officer and Director, Teladoc Health, Inc. (NYSE: TDOC) ("Teladoc"), 2009-͏2024

• •Various management roles, Elevance Health, Inc. (formerly known as Anthem, Inc. and WellPoint, Inc.), including as President, Empire BlueCross BlueShield

• •Leadership roles at Oxford Health Plans, Inc., Mail.com, and Gemfinity

REASONS FOR NOMINATION

Age: 53

Director since: 2022

Skills:

• •Executive Experience

  Mr. Gorevic is an experienced leader in the health care industry. From 2009 to 2024, he served as the chief executive officer of Teladoc, a global leader in virtual medical care. His knowledge and experience gained as a corporate leader and entrepreneur is of great value to the Kemper Board. He has executive experience in risk management, strategic planning, and corporate transactions.

• •Accounting / Finance

• •Risk Management

• •Regulatory / Policy

  The Board believes his significant first-hand knowledge of leading and operating a technology-focused, consumer-facing business in a regulated industry is of great benefit to Kemper and its businesses.

• •Corporate Governance

• •Consumer-Focused Business

• •Business Development

• •IT / Cyber

Lacy M. Johnson

CURRENT ROLE

• •Partner-in-charge, Public Affairs Strategies Group, Taft Stettinius & Hollister LLP, 2021-Present

• •Director, Kemper Corporation, 2016-Present

• •Director, Griffon Corporation (NYSE: GFF), 2019-Present

BACKGROUND & PAST EXPERIENCE

• •Partner, Ice Miller LLP

• •Attorney, Governmental Relations Services, Sagamore-Bainbridge, Inc.

• •Director of Security, Indiana State Lottery (liaison with the Indiana General Assembly)

Committees:

Governance, HR&CC

REASONS FOR NOMINATION

Age: 72

Director since: 2016

Skills:

• •Insurance Industry

• •Regulatory / Policy

  Mr. Johnson is a senior attorney and public servant with wide experience in governmental and regulatory affairs. His knowledge of these matters, gained over his 30 years in legal practice, provides the Board with important insight on government relations at the state and federal levels. In addition, Mr. Johnson has provided focused insight on Kemper's "act like an owner" culture, its corporate responsibility practices, diversity considerations, and other human capital priorities.

• •Human Capital

• •Corporate Governance

• •Corporate Responsibility

• •IT / Cyber

The Board also values Mr. Johnson's distinguished public service and leadership. He is a trusted advisor to many leaders and members of the Congressional Black Caucus and is a Democratic National Committeeman. Mr. Johnson's public service includes participation on the governing bodies of many civic and educational institutions, including roles with the Indiana University Foundation and the Krannert School of Management at Purdue University. He also served as a Lieutenant Commander in the United States Naval Intelligence Reserves and as a Lieutenant Colonel and Deputy Superintendent for Support Services of the Indiana State Police.

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Disclaimer

Kemper Corporation published this content on March 26, 2025, and is solely responsible for the information contained therein. Distributed by Public, unedited and unaltered, on March 26, 2025 at 15:35:21.270.