PROGRESSIVE CORP/OH/

This summary highlights certain information contained in this Proxy Statement. This summary also highlights how we approach our business, contains 2025 business performance highlights, and discusses our approach to environmental and social (sustainability), corporate governance, and human capital management.

The Proxy Statement Summary does not contain all of the information you should consider when voting your shares. Please read the entire Proxy Statement and Annual Report to Shareholders carefully before voting. For additional information about how to vote your shares, including voting options and standards, see “Questions and Answers about the Annual Meeting and Voting” in this Proxy Statement.

VOTING MATTERS AND BOARD RECOMMENDATION

PROGRESSIVE AT A GLANCE

The Progressive insurance organization has been offering insurance to consumers since 1937. We are the second largest private passenger auto insurer in the U.S., the largest writer of motorcycle insurance, the twelfth largest homeowners insurance carrier, and the number one writer of commercial auto insurance, in each case based on 2024 premiums written.

As our name implies, we were founded on the principle of moving forward, taking new risks, and learning and growing together. As we look to the future, we are grounded in our four cornerstones—who we are, why we are here, where we are headed, and how we will get there—which drive our competitive advantage and allow all people associated with us to understand what we expect of ourselves and each other and how we conduct our business.

OUR CORE VALUES: Who we are

Progressive’s Core Values—Integrity, Golden Rule, Objectives, Excellence, and Profit—serve as the foundation for our culture. They represent our values, guide our decisions, and define how we conduct our business and interact with others.

•Integrity: We revere honesty and adhere to high ethical standards to gain the trust and confidence of our customers. We value transparency, encourage disclosing bad news, and welcome disagreement.

•Golden Rule: We value and respect our differences, act with kindness and caring, and treat others as they want to be treated.

•Objectives: We set ambitious goals and evaluate our performance by measuring what we achieve and how we achieve it. We’re committed to an inclusive and equitable workplace where rewards and promotion are based on results and ability.

•Excellence: We strive to meet or exceed the expectations of our teammates, customers, partners, and investors by continuously improving and finding new ways to meet their needs.

•Profit: We have a responsibility to ourselves, our customers, agents, and investors to be a profitable and enduring company by offering products and services consumers value.

OUR PURPOSE: Why we’re here

Progressive exists to help people move forward and live fully.

OUR VISION: Where we’re headed

Our Vision is to become consumers’, agents’, and business owners’ #1 destination for insurance and other financial needs.

OUR STRATEGY: How we’ll get there

We will achieve our Vision through four Strategic Pillars: (1) Ensuring that our people and culture collectively remain our most powerful source of competitive advantage; (2) Meeting the broader needs of our customers throughout their lifetimes; (3) Maintaining a leading brand recognized for innovative offerings and supported by experiences that instill confidence; and (4) Offering competitive prices driven by industry-leading segmentation, claims accuracy, and operational efficiency.

2025 BUSINESS PERFORMANCE HIGHLIGHTS

As a property-casualty insurance company offering products throughout the U.S., we have earnings streams from both underwriting activity and investment activity. During 2025, we wrote $83.2 billion of net premiums written, or $8.8 billion more than the prior year, and ended the year with 38.6 million policies in force, which was an increase of 3.7 million from year-end 2024. Our underwriting profit margin for 2025 was 12.6% (which exceeded our companywide profitability target of at least 4%), or $10.2 billion of pretax underwriting profit, compared to 11.2%, or $8.0 billion, for 2024. Several factors contributed to the increase in underwriting profit margin over the prior year, including lower personal and commercial auto accident frequency, lower weather-related catastrophe losses, and favorable prior accident years development, partially offset by $1.2 billion of policyholder credit expense related to personal auto excess profits earned in Florida.

Our investment portfolio generated $3.6 billion of recurring investment income during 2025, compared to $2.8 billion in 2024. The 27% increase reflected growth in invested assets and an increase in recurring investment book yield. At December 31, 2025, 85% of the total fair value of our portfolio was comprised of fixed-maturity securities. During 2025, the changes in the market value of our fixed-maturity securities, which are a component of comprehensive income, increased $1.5 billion, after tax, due to valuation increases across all fixed-maturity sectors. For the year ended December 31, 2025, our fully taxable equivalent total return on our investment portfolio was 7.3%.

During 2025, we declared aggregate common share dividends of $13.90 per share, which includes both our annual-variable and quarterly common share dividends of $13.50 per share and $0.10 per share, respectively, and repurchased 0.7 million of our outstanding common shares, at an average cost of $237.44 per common share. We ended 2025 with $37.2 billion of total capital and a debt-to-total capital ratio of 18.5%.

Following are a few key performance metrics for 2025:

We encourage you to review our Annual Report to Shareholders for additional information on our 2025 performance and our financial results.

NOMINEES FOR DIRECTOR

The Board has nominated 11 directors, each of whom is a current director, with a broad and complementary set of backgrounds, experiences, perspectives, and skills.

Diversity

Skills and Experiences

CORPORATE GOVERNANCE HIGHLIGHTS

Corporate Governance Practices

We are committed to meeting high standards of ethical behavior, corporate governance, and business conduct. Some of our corporate governance practices include:

Board Risk Oversight

The Board is ultimately responsible for overseeing our risk profile and risk management processes. To facilitate these responsibilities, the Board assigns certain risk oversight responsibilities to each of its main committees through each committee’s charter. The committees continue to undertake the increasingly detailed oversight work for which they are responsible, to interact with and oversee management, and to report back significant matters to the full Board. See the “Board Risk Oversight” section of this Proxy Statement for a more detailed discussion.

SUSTAINABILITY HIGHLIGHTS

Sustainability matters and corporate governance initiatives have been an integral part of our business. Our Core Values are a cornerstone of our business and, as such, are the tenets of these initiatives and have evolved naturally as we work to not only grow our business, but also to support our customers, community, and employees.

The Board’s Approach

The Board and its committees oversee the assessment and management of various sustainability and corporate governance matters. In their oversight role, our directors ask questions, probe our thinking, provide strategic input, and give guidance informed by their diverse backgrounds, experiences, perspectives, and skills. The following chart highlights some of our Board’s involvement with these matters.

Our Sustainability Efforts

At Progressive, we aim to take a forward-looking approach to everything we do, from the products we offer to the way we interact with the world around us. We work to drive sustainable change for our shareholders, employees, independent agents, communities, and the millions of customers who trust us to protect what is important to them.

Our most recent Corporate Sustainability Report was prepared with guidance from the Nominating and Governance Committee, our executive leadership, and various subject matter experts. The report was informed by elements from various reporting frameworks, namely the Sustainability Accounting Standards Board (SASB) and the Task Force on Climate-Related Financial Disclosure (TCFD), and includes indices to each of these reporting frameworks. The report is intended to connect our sustainability-related investments in our operations, people, and culture, with our commitment to driving sustained, long-term business value for shareholders. The report provides information regarding our philosophy and practices on a number of topics, including:

To review our most recent Corporate Sustainability Report, including the limited assurance report by an independent third party of our Scope 1 and Scope 2 location-based and market-based greenhouse gas emissions reporting, please visit progressive.com/sustainability. The report and any other information on the sustainability site are not incorporated by reference in, and do not form part of, this Proxy Statement or any other Securities and Exchange Commission (SEC) filing.

HUMAN CAPITAL MANAGEMENT

We believe that our people and our culture remain our most significant competitive advantage, and that having the right people working together in the right way is critical to driving our results, building our enduring business, and creating long-term shareholder value. Our culture is deeply rooted in our Core Values and is the foundation for our human capital management strategies to attract, hire, engage, and retain highly qualified employees.

Our People

We believe that our culture and continued success has enabled us to create a workplace composed of highly talented people across diverse markets and with a broad range of backgrounds and experiences. They create innovative products and services, serve our customers, and work hard to help us achieve our Vision.

Attract and Hire We employ extensive recruiting practices with a goal of developing qualified and deep candidate pools and attracting candidates from both established and new sources. We believe that our recruitment efforts generally have enabled us to present pools of high-potential job candidates to our hiring managers. In turn, we train our hiring managers to identify and avoid unconscious biases they may have during the interview and selection process. We also train our hiring managers on the importance of employing individuals with different kinds of backgrounds, experiences, perspectives, and skills. We believe these strategies collectively enhance our ability to hire the best candidate for each of our openings and contribute to our continued success.

Engage and Retain We appreciate that engaged employees are more productive, provide better service to our customers, and are more likely to stay with Progressive. Each year, we survey our people to measure their engagement. We use the results, along with other information, to evaluate our human capital strategies and the health of our culture.

Employee retention is an important part of our strategy. Promoting from within also is a key part of our strategy. Many of our leaders, including all executive team members, joined Progressive in a more junior position and advanced to significant leadership positions within the organization. As of December 31, 2025, we had over 70,000 employees. We disclose our consolidated EEO-1 data on our website.

Supporting our People and Culture

We strive to support our employees by providing challenging work experiences, career opportunities, and a culture of learning. We aim to provide a work environment that enables employees to present innovative ideas, share differing viewpoints, and constructively challenge assumptions.

We believe this approach has helped the company expand and grow our businesses and create additional career opportunities for our employees.

Training and Development We are focused on coaching and development, which we believe promotes greater engagement in our business and improves individual performance. We actively foster a learning culture and offer several leadership development programs, including a program open to employees with a focus on leading inclusively. Moreover, we endeavor to provide employees with the tools and support to excel in their roles and build long-term careers at the company. Our professional development resource, “Career Central,” encourages employees to take control of their careers through career exploration guides, video insights, sample career journeys, discovery questionnaires to guide employees to roles that match their skills, and more. Available to new and tenured employees, our learning solutions are tailored to both individual contributors and leaders and cover a broad swath of skills and competencies.

ERGs Our first Employee Resource Groups (ERG) were created in 2007 to help build communities for our employees and drive business impact. We believe our ERGs, which are each open to all employees at the company, provide spaces for networking, understanding differences, and sharing experiences. In addition to enhancing our work environment, we believe our ERGs give the company valuable insights to better serve our customers. Additionally, we believe that ERG members are more engaged and more likely to stay with the company. Nearly 44% of Progressive people belong to at least one of the following ERGs as of December 31, 2025:

•Asian American Network

•Disabilities Awareness Network

•LGBTQ+ Network

•Military Network

•Network for Empowering Women

•Parent Connection

•Progressive’s African American Network

•Progressive’s Latin American NETworking Association

•Young Professionals Network

Compensation and Benefits As part of employee compensation, nearly all Progressive people participate in our annual cash incentive program, named Gainshare, which measures the growth and profitability of our insurance businesses. We believe Gainshare contributes to the cooperative and collaborative way we work together and, in part, defines our culture. We also monitor overall pay equity among employees with similar performance, experience, and job responsibilities, and publish the results annually on our website.

Additionally, our employee benefits are intended to be competitive and to support the needs of our people and their families. We invest in the health and wellbeing of Progressive people by providing a broad range of benefits.

Supporting An Inclusive Workplace

We believe that in order to be consumers’, agents’, and business owners’ number one destination for insurance and other financial needs, we need to anticipate and understand the needs of our customers. Therefore, we aspire to take full advantage of the rich diversity of our employees’ unique backgrounds, experiences, perspectives, skills, and talents. Our work environment and talent management efforts are overseen by our Compensation and Talent Committee on behalf of the entire Board.

We challenge ourselves to reach far and wide to attract highly qualified and deep applicant pools when recruiting opportunities arise, and to invest broadly in developing our internal talent.

We’re committed to creating an environment where all our people feel welcomed, valued, and respected, and we integrate this commitment into our workplace. This includes hosting regular IQ Inclusion Quarterly® events which feature a series of speakers, discussion groups, and storytelling focused on themes such as embracing vulnerability and increasing collaboration.

Moreover, we support efforts to contribute to our communities, through our Keys to Progress® program (which provides vehicles to veterans and veteran-related organizations), and by supporting programs which furnish homes for individuals emerging from homelessness, our various education and engagement efforts, and our financial contributions to various community organizations.

For over 20 years, we also have contributed to The Progressive Insurance Foundation (Foundation). Through the Name Your Cause® program, each employee can recommend an eligible charity to receive a fixed amount of the Foundation’s charitable giving without requiring the employee make an out-of-pocket donation. This is the Foundation’s way of supporting causes and reaching communities across the country where our people and our customers live and work. Since 2020, Progressive has also contributed, either directly or through the Foundation, to national charitable organizations identified by our ERGs.

See “Compensation Discussion and Analysis – Elements of Compensation – The Role of Supporting An Inclusive Workplace” for more information.

EXECUTIVE COMPENSATION HIGHLIGHTS

We believe that our executive compensation program has been a critical component of our strong operating results and, in turn, shareholder returns in recent years. We generally provide our executives with base salaries near or below the market median and a significant percentage of total compensation in the form of performance-based equity awards. The performance-based equity awards provide upside potential when we outperform challenging pre-established and objective measures that we believe correlate to shareholder value. In furtherance of our long-standing goal to grow as fast as we can at a 96 or better combined ratio while continuing to deliver high-quality customer service, we use the combined ratio as a performance measure in several compensation elements.

We believe that the overall structure of our executive compensation program supports a strong pay-for-performance linkage and aligns the interests of our executives with those of our shareholders. For example, during the past five years:

•we grew faster than the markets of the insurance business lines we measure, resulting in the related vesting of the performance-based restricted stock unit awards above target;

•we achieved long-term fixed-income portfolio returns in line with our benchmark, resulting in the vesting of the performance-based restricted stock unit awards that reflect our investment results near or above target; and

•our annual Gainshare program payout has ranged from 86% to 199% of target, with an average of 161% of target, based on the growth in average policies in force and profitability of our insurance businesses (for 2025, it paid out at 199% of target).

Our executive compensation program is overseen by the Compensation and Talent Committee of the Board. The committee’s decisions are made after considering third-party compensation data for comparable companies, internal analyses, and recommendations presented by management. The executive compensation decisions for executive officers generally represent the culmination of extensive analysis and discussion, which typically take place over the course of multiple committee meetings and in meetings between the committee and management, including our Chief Executive Officer (CEO), our Chief Human Resources Officer, members of our compensation and legal groups, and sometimes compensation consultants.

Our executive compensation program has a number of important structural features and guiding policies. Below are the executive compensation practices we follow:

STAKEHOLDER ENGAGEMENT

We seek to provide transparency into our business, our performance, our strategic priorities, our governance practices, and how our Core Values guide our decisions and support our culture. We share information with our stakeholders in a variety of ways, including monthly earnings releases, quarterly investor calls, annual shareholder meetings, quarterly letters from our CEO, and annual letters from our Chairperson of the Board.

We recognize the value in maintaining open lines of communication with our stakeholders and engage with our stakeholders throughout the year to:

•provide visibility and transparency into our business, our performance, and our corporate governance, sustainability, and compensation practices;

•discuss with our investors the issues that are important to them, hear their expectations for us, and share our views; and

•assess emerging issues that may affect our business, inform our decision making, and enhance our corporate disclosures.