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 9, 2025, 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/PGR2025. To participate in the Annual Meeting, you must have your 16-digit control number that is shown on your 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 2025; 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 14, 2025, are entitled to receive notice of and to vote at the meeting or any adjournment or postponement of the meeting.

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 enclosed proxy card), or by completing and returning the proxy card in the enclosed postage-paid envelope. 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,

The Proxy Statement and the 2024 Annual Report to Shareholders

are also available at progressiveproxy.com

A MESSAGE FROM THE BOARD OF DIRECTORS

To Progressive’s shareholders:

After navigating several years of challenging business conditions, we welcomed 2024 with cautious optimism. We believed Progressive’s deft response to volatility and profitability concerns in 2023 positioned it well for profitable growth in 2024. Our optimism proved well-grounded: The company delivered an appealing mix of product offerings and customer-focused service, yielding a year of profitable growth.

The numbers tell a lot of the story. Year over year, Progressive grew countrywide policies in force and net written premiums by 18% and 21%, respectively. This follows strong growth in 2023, marking exceptional sustained performance. Moreover, both our Personal Lines and Commercial Lines businesses were profitable—no small feat in highly competitive markets and uncertain risk environments. The results are a testament to Progressive’s unwavering commitment to growing as fast as possible while delivering outstanding customer service and earning at least a four percent profit margin.

While my fellow Directors and I were delighted with the company’s results, 2024 was about more than numbers. In a decade filled with change and challenge, obstacles and opportunities, we believe Progressive’s performance has been rooted in the team’s clarity of vision, excellence in execution, and sincerity of culture. We’re confident these strengths, amplified through over 66,300 Progressive employees, will continue to support an enduring, thriving business. It is a joy to watch the Progressive team work together with shared purpose and cultivated resilience.

I encourage you to read more about Progressive’s outstanding performance in 2024 in the most recent letter from Progressive’s Chief Executive Officer, Tricia Griffith, which accompanies our 2024 Annual Report. As always, Tricia’s letter provides a view into Progressive’s unique culture, gives context to its commitments to its stakeholders, and shares details about Progressive’s accomplishments, strategies, and goals.

With regard to stakeholders, the Board recognizes the special role Progressive plays for its customers

and employees during times of need. We saw this firsthand at our October 2024 Board meeting, which commenced the morning after Hurricane Milton made landfall in Florida. Immediately, the Progressive team pivoted to focus on the storm. We received real-time updates as plans were made to mobilize thousands of employees to contact customers and address claims—and to reach out to employees in the storm’s path to check on their safety and offer assistance to those needing help. We saw the urgency of the moment, the concern for everyone’s welfare, and the desire to be there for both customers and employees in need. Ultimately, customers were served, employees were supported, and the company played its perennially vital role in the process of repairing and rebuilding. This is just one example of how Progressive lives up to its brand purpose – coming together as a team to help our customers move forward and live fully.

I could fill pages with commentary on the company’s efforts for other stakeholder groups. For more on that, I invite you to read Progressive’s Corporate Sustainability Report, published this past September. In those pages, you’ll find data and stories that illustrate the driving force of culture at Progressive. The team strives to understand each other’s needs, its customers’ needs, and the overarching need to deliver when it counts, always in the right way.

As a Board, we are ever mindful of the critical role we play in providing oversight and input. To that end, we continue to engage with management regularly on overall business strategy, risk management, and issues relating to people and culture, among many other matters. This includes overseeing both “here and now” risks and strategies and longer-term challenges and opportunities. Each year, we meet with Progressive leaders across various business functions to take deep dives into key company initiatives and to stay informed of business operations, the competitive landscape, and company plans. We so enjoy engaging not only with Progressive’s most senior leaders, but with emerging talent across the organization. We do this both as a full Board and through our committees.

We’re also mindful that strong corporate governance starts with us. My fellow Directors and I ensure we remain committed to strong corporate governance practices, and we engage with the Progressive team through that lens. We ask questions, offer perspectives, and exercise oversight with an eye fixed on long-term shareholder value. In doing so, we find that our varied backgrounds, experiences, and perspectives serve us well and enrich our oversight. It truly is a team made stronger by our differences, which we focus collaboratively on our shared commitment to service to Progressive’s shareholders. We note with sadness the passing of our former colleague and friend, U.S. Navy Rear Admiral (Retired) Danelle Barrett. We miss her insights and her dedicated participation in our work.

Our Annual Meeting this year will be held virtually on May 9, 2025. We encourage you to attend. Even if you don’t plan to attend the meeting, we hope you will review our proxy statement and vote your shares.

On behalf of the Board of Directors, I thank all of Progressive’s over 66,300 employees for their incredible work and commitment during 2024, and I thank you for your ongoing investment in The Progressive Corporation.

/s/ Lawton W. Fitt

Lawton W. Fitt

Chairperson of the Board

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