A letter from the PRESIDENT AND CEO | 2 A letter from the CHAIRMAN | 4 BOARD OF DIRECTORS | 5 A letter from the BOARD OF DIRECTORS | 6 OPERATING MANAGEMENT Committee | 7 LINES OF BUSINESS Review | 8 FINANCIAL Highlights | 10 SHAREHOLDER Information | 11 2019 ESG Highlights | 12 A letter from the PRESIDENT AND CEO Dear Shareholders, I am pleased to report Webster’s 2019 results. We remain committed to purposeful execution on our strategic priorities: aggressively growing HSA Bank, expanding Commercial Banking and optimizing Community Banking. We continue to focus on building long-term franchise value and maximizing economic profits over time through solid execution, a disciplined approach to capital allocation, prudent risk management and a strong commitment to our customers, employees, shareholders, and the communities we serve. We generated solid economic profit again this year, as our 2019 return on common equity of 12.8% and our return on tangible common equity of 16.0%, were both well in excess of our stated 9.5% cost of capital. Earnings per share (EPS) were 6.5% higher than last year and represented our 10th consecutive year of EPS growth. Webster’s full-year common dividend was 22% higher than a year ago; full-year revenue of $1.2 billion was a record for the Bank, and represented our 10th consecutive year of revenue growth. Pre-provision net revenue grew 8.4%, driven by a 4.3% increase in revenue and a 1.5% increase in expenses, demonstrating positive operating leverage for the year. We continued to report strong organic loan and deposit growth across all lines of business. Loans grew 9%, with commercial loan growth of 10% leading the way. Total deposits grew 7%, led by 12% growth in our differentiated HSA business. We continue to enjoy a favorable loan to deposit ratio of 86%, which provides us significant flexibility going forward. Our capital levels remain strong and well in excess of regulatory minimums. Our focus on enterprise-wide risk management underpins everything we do. Our strategic management framework provides a disciplined approach to managing credit, operational, cyber and reputational risks. Credit quality remained strong in 2019, with many credit metrics near or at cycle lows. We proactively monitor our loan portfolios in order to ensure that we understand credit migration, portfolio concentrations and performance trending. Our information security program recently earned the CSO50 Award for our initiative addressing next-generation security strategies. We are proud of this recognition and remain committed to protecting our customers’ data and the Bank’s assets. Webster continued to make meaningful advancements in our deployment of technology as we deliver mobile and digital products and services, provide technology solutions for our bankers to more efficiently and effectively serve our customers, and ensure that customer information remains secure and safe. This will remain a critical focus. Successful execution in technology will also allow us to significantly reduce our overall cost of delivery for both products and services. I encourage you to read our 2019 Environmental, Social and Governance (ESG) Report, as we are proud of our long history of being a responsible corporate citizen. The Report illustrates our leadership on sustainability, diversity and inclusion, and transparent governance. STRENGTH IN NUMBERS $1.2 10th 56.8% 12.8% 16.0% BILLION CONSECUTIVE EFFICIENCY RETURN RETURN TOTAL ANNUAL FULL YEAR OF EPS AND RATIO ON COMMON ON TANGIBLE REVENUE REVENUE GROWTH EQUITY COMMON EQUITY Webster Financial Corporation 2019 Annual Report | 2 We continued to invest in the expansion of our diversity and inclusion programs, including our Webster Women’s Initiative Network (WeWIN). Webster hosted several WeWIN events during the year, including a panel discussion with our four women Directors, all of whom were recently named “Most Influential Corporate Board Directors” by WomenInc. Throughout Webster’s 85-year history, our engaged bankers have always been our most valuable asset, and we remain committed to providing them with a healthy, fulfilling, diverse and inclusive workplace. We continue to invest in our people, through technical and leadership development, and through the expansion of our early career programs. In the wake of the federal government shutdown in late 2018, the State of Connecticut asked Webster to take the lead in a public-private partnership to assist federal employees in January 2019. Webster created the Connecticut Hardship Assistance Program, an interest-free loan program to assist federal employees who were required to report to work without pay. Webster received many external recognitions of our commitment to excellence this past year. We were ranked seventh most reputable bank in the nation by the Reputation Institute; we were recognized for our Board’s gender diversity by 2020 Women on Boards; and Forbes named us as one of America’s Best Banks. Consistent with our thoughtful leadership succession process, Chairman Jim Smith announced that he will be retiring from Webster’s Board of Directors effective at our Annual Shareholders Meeting in April 2020. Webster’s Board has elected me to succeed Jim, and I’m honored to have the Board’s confidence. I also appreciate their support and engagement as we move forward with our clearly defined strategies. On behalf of all Webster bankers, I’d like to recognize Jim’s dedication and commitment to Webster and its stakeholders over the course of his distinguished career. He has shaped the Webster Bank legacy, and he is nationally recognized as a leader in the banking industry. I’d also like to thank Jim personally for his guidance and friendship, particularly during the period of transition. He is truly a remarkable person. As I write this letter to shareholders, events such as the emergence of COVID-19 and other global pressures have created uncertainty and volatility in our daily lives, as well as in the capital markets and the macroeconomic outlook. This will make 2020 more challenging for all of us, but the safety of our bankers and customers remains a top priority. Webster is prepared to meet the challenges that may arise, and we will continue to deliver value for all of our stakeholders. As always, I would like to acknowledge our 3,400 values-based bankers for their outstanding contributions and their unwavering commitment to our customers, our communities, and to each other. Working together, Webster will achieve our vision of becoming the highest performing mid-sized bank in the country. Thank you for your continued confidence in Webster. Sincerely, John R. Ciulla President and Chief Executive Officer $ $4.06 20.0 $3.81 Webster’s 2019 ESG Report illustrates our leadership $2.67 $18.5 on sustainability, diversity and inclusion, and $17.5 transparent governance. See highlights on page 12 2017 2018 2019 2017 2018 2019 EARNINGS PER SHARE LOANS $ in Billions Webster Financial Corporation 2019 Annual Report | 3 A letter from the CHAIRMAN Dear Shareholders, In January, I announced my retirement as Chairman effective at the 2020 Annual Meeting, at which time President and Chief Executive Officer John Ciulla will assume the additional responsibilities of Chairman. As I write to you for the final time as Webster’s Chairman, our leadership transition now complete, I feel a sense of professional fulfillment. Among a leader’s highest responsibilities is to develop future leadership. I retired as CEO two years ago because John Ciulla was ready to take the reins of ongoing transformation at Webster. John has exceeded our expectations, moving the Company smartly forward, guided by a strong sense of purpose and supported by a stable, highly committed management team and 3,400 Webster bankers who make a difference in the lives of their customers and communities they serve. Webster’s Board and I believe that this Company’s leader should serve as both CEO and Chairman, as I did for 22 years. Assuming these roles sequentially has allowed John valuable time for acclimation as CEO before also becoming Chairman. This dual role is supported by our Board’s attentive oversight of governance and risk matters, as well as the active engagement of our Lead Independent Director, now Bill Atwell, following John Crawford’s exemplary service. Webster’s diverse and caring Board will be a continuing source of strength to John and our shareholders. I know from your feedback that shareholders have been pleased with the way we’ve handled the CEO and now Chairman successions. I know that my father, Webster’s founder Harold Webster Smith, would be pleased, too. My sense of fulfillment derives in large part from knowing that Webster is stronger than ever before, as measured by our differentiated strategies, financial performance, capital strength, quality of risk management and organizational stability. Our culture brings us together and sets us apart in the marketplace… it’s the context in which we compete. I’m proud to say that Webster has operated as a purpose-driven company for 85 years. In today’s highly competitive, fast-changing world, we maximize value for shareholders by excelling in service to all of our stakeholders. We invest considerable time, talent and financial resources in the communities we are privileged to serve. When I joined Webster in 1975, we were a small thrift institution with five offices, about 50 bankers and a great leader, my father, serving greater Waterbury, Connecticut. Today we’re a $30 billion commercial bank operating under a national charter, listed on the NYSE, and the largest bank administrator of health savings accounts. Over the years our mission has evolved and our vision has expanded. The one constant has been our enduring values of responsibility, respect, trustworthiness, citizenship and teamwork (The Webster Way). I will always be grateful to our Webster bankers who have lived up to our customers and communities for generations, including their amazingly compassionate actions during the Great Recession.