PROGRESSIVE CORP/OH/

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. )

(Name of Registrant as Specified In Its Charter)

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

The Progressive Corporation (NYSE:PGR) will hold its Annual Meeting of Shareholders on Friday, May 8, 2026, at 10:00 a.m. Eastern Time. The meeting will be held by online audio webcast only and there will be no physical location for the meeting. Accordingly, you will not be able to attend the Annual Meeting in person. You will be able to attend the Annual Meeting, vote, and submit your questions during the meeting via live audio-only webcast by visiting virtualshareholdermeeting.com/PGR2026. To participate in the Annual Meeting, you must have your 16-digit control number that is shown on your Notice of Internet Availability of Proxy Materials or proxy card.

At the Annual Meeting, shareholders will be asked to:

1. Elect as directors the 11 nominees identified in the attached Proxy Statement, each to serve for a term of one year;

2. Cast an advisory vote to approve our executive compensation program;

3. Ratify the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for 2026; and

4. Transact such other business as may properly come before the meeting.

The foregoing items of business are described more fully in the Proxy Statement accompanying this Notice. Only shareholders of record of The Progressive Corporation at the close of business on March 13, 2026, are entitled to receive notice of and to vote at the meeting or any adjournment or postponement of the meeting. On or about March 23, 2026, we mailed a Notice of Internet Availability of Proxy Materials and printed copies of our proxy materials, if requested, to our shareholders. The Notice of Internet Availability of Proxy Materials provides instructions on how to access our proxy materials via the Internet and how you can obtain printed copies of our proxy materials.

Your vote is important. Whether or not you plan to participate in the meeting via the live audio-only webcast, please vote by Internet or telephone (following the instructions on the Notice of Internet Availability of Proxy Materials or the enclosed proxy card, if the Proxy Statement was mailed to you), or by completing and returning the proxy card (in the enclosed postage-paid envelope if you received a printed copy). If you later choose to revoke your proxy or change your vote, you may do so by following the procedures described in the Proxy Statement’s “Questions and Answers about the Annual Meeting and Voting” section.

By Order of the Board of Directors,

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING OF SHAREHOLDERS TO BE HELD ON MAY 8, 2026:

The proxy materials, including the Proxy Statement and the 2025 Annual Report to Shareholders

are available at progressiveproxy.com

A MESSAGE FROM THE BOARD OF DIRECTORS

To Progressive’s shareholders:

It is my pleasure to write to you on behalf of my fellow directors as we look back on another successful year and ahead to a promising future.

Progressive’s success is rooted in its ability to recognize, act on, and create opportunity. Through innovations in products and services, deliberate investments in people and culture, a relentless drive for improvement, and a steadfast commitment to its Core Values, Progressive consistently seeks and finds ways to delight its customers, engage its people, and deliver long-term, sustainable growth. In that spirit, my fellow directors and I were confident that Progressive could build on its remarkable performance in 2024 to deliver another outstanding year in 2025. And so it did.

Progressive’s performance in 2025 was remarkable by every measure. Just a few of the highlights that stand out to me are companywide policies in force growth of 10%, and companywide net premiums written growth of 12%. This growth was profitable across segments, and Progressive ended the year with a strengthened balance sheet and a debt-to-capital ratio of 18.5%, enabling us to return capital to our shareholders through stock purchases and a robust annual-variable dividend. We were just as pleased that Progressive ranked in the 99 th percentile of companies in its annual engagement and culture survey in 2025, a continued testament to strong leadership, outstanding talent management, and exceptional investments in workplace culture.

As I do every year, I encourage you to read the most recent letter from Progressive’s Chief Executive Officer, Tricia Griffith, which accompanies the Annual Report. Tricia has a special knack for bringing business measures to life, sharing not only thoughtful perspective but messages she’s received during the year from customers and employees for whom Progressive made a difference. These accounts humanize the work Progressive does every day. Tricia’s letter also offers a thoughtful reflection on the products, people, operations, and strategies that supported Progressive’s success throughout 2025.

Broadening the horizon to the past five years, I’m delighted that Progressive’s longer-term results reflect the same disciplined execution anchored in clear strategic vision that informed the year just ended. During this five-year period, Progressive:

•delivered annualized rates of return on net income and comprehensive income of 26.0% and 25.2%, respectively;

•outpaced the S&P 500 by 1.6x and exceeded its peer group by 1.2x for total shareholder return;

•achieved annualized growth in net premiums written by 15%;

•maintained underwriting profitability aligned with its long-term 96 combined ratio target; and

•responsibly increased policies in force at a 9% annualized growth rate.

These achievements underscore the strength of our long‑term mindset and our commitment to building an enduring business. And on an industry-wide basis, Progressive’s five-year annualized underwriting margin of 8.3% and net premiums written growth of 15%, exceeded the industry’s underwriting margin of (0.4)% and net premiums written growth of 7%, in each case based on 2024 U.S. private passenger auto premiums written.

As Progressive grows, its opportunity to impact others grows in step. Progressive’s Purpose is to help people move forward and live fully. This weighty goal reflects the essential role that insurance plays in enabling people, businesses, and communities to pursue their own opportunities with confidence that Progressive will be there for them when needed. Last year I shared the Board’s observations of Progressive’s response to damaging hurricanes in 2024. While many communities were fortunate that the past year’s hurricane season was not as damaging, there were nonetheless many lives, families and businesses impacted by insured events, and Progressive’s people once again leapt into action wherever and whenever needed.

For a deeper look at how various initiatives support our business operations, financial performance, and Core Values, I invite you to read Progressive’s Corporate Sustainability Report, published this past September, which includes examples of teams striving to support one another, meet customer needs, and rise to the moment when it matters most. I’m confident you’ll appreciate the company’s commitment to culture, to ethical business practices, and to long-term sustainability.

My fellow directors and I believe opportunity expands through a purposeful long-term strategy and steadfast adherence to Progressive’s Core Values. These principles guide our oversight and reinforce our responsibility as stewards of your investment. We work closely with management throughout the year to evaluate competitive positioning, capital deployment, operational capabilities, and long‑term priorities, among other things. We enjoy bringing our varied backgrounds, experiences, perspectives, and skills to bear on these strategic discussions with management, which we invariably leave with confidence and enthusiasm.

We remain closely involved in overseeing key risks, working with management throughout the year to review and assess strategic, operational, and emerging risks. In recent years, we’ve dedicated focused attention to cybersecurity, to responsible use of artificial intelligence, and to fostering strong leadership and a healthy, inclusive culture. We recognize that Progressive’s people, the technologies they use, and their facility with emerging tools—and awareness of evolving customer, community, and employee preferences and expectations—are central to Progressive’s long-term success. Through both committee work and full Board oversight, we aim to support Progressive’s enduring strength and ensure the company continues to thrive for years to come. As with our engagement on opportunities, our engagement on risks is all the richer for the variety of experiences and knowledge we bring to these discussions.

In keeping with past years, the Board engaged at length with Progressive people throughout 2025. This is its own form of opportunity—for us and for Progressive’s people—and is incredibly meaningful to us. We connected not only in the boardroom and in committee meetings, but through mentoring, employee resource group events, and broader leadership programs. We met with employees across levels and functions and gained firsthand insight into the many ways Progressive’s Core Values guide their everyday work. These interactions reaffirm for us the distinctive strength of Progressive’s people and culture.

As we enter 2026, we are optimistic about the opportunities ahead. Progressive’s identity is rooted in moving forward—innovating, adapting, and striving to be better. With a strong strategy, disciplined execution, robust corporate governance processes, and a culture that attracts and retains exceptional people, the Board believes that Progressive is well positioned to continue creating long-term value for our customers, employees, independent agents, communities, and shareholders.

Our Annual Meeting this year will be held virtually on May 8, 2026. We encourage you to join. Even if you do not plan to attend, we hope you will review our proxy statement and vote your shares.

On behalf of the Board of Directors, I want to thank our 70,000 Progressive employees for everything you accomplished in 2025—your hard work and dedication truly made a difference. And to our shareholders, I want to thank you for your confidence and continued investment in The Progressive Corporation.

Sincerely,

/s/ Lawton W. Fitt

Lawton W. Fitt

Chairperson of the Board

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