We Are The Andover Companies

Charles “Chuck” DiGrande has spent the entirety of his 33-year career at The Andover Companies. Directly after graduating from Colby College in 1993, he joined the company’s Personal Lines Underwriting team, starting off as an assistant underwriter. Over the next 22 years, Chuck earned successive promotions to Underwriter, Senior Underwriter, and Personal Lines Underwriting Director. In 2015, Chuck was promoted to Assistant Vice President and product owner responsible for overseeing the Core System Replacement project, a crucial long-term initiative for the company. Chuck was promoted again in 2017, taking on the role of Vice President of Underwriting, which gave him oversight of Personal Lines Underwriting, Commercial Lines Underwriting, Underwriting Product Development, and Reinsurance. In 2020, Chuck was promoted to President of The Andover Companies, and the following year, he was also appointed Chief Executive Officer. In addition to his enterprise leadership role at The Andover Companies, Chuck serves as Vice Chair of the Board of Directors of the Massachusetts FAIR Plan and is a board member of the Mutual Fire Insurance Association of New England. He is also the former chair of the Governing Committee of the Rhode Island Joint Underwriting Association.

Paul Nadeau joined The Andover Companies after graduating from Bowdoin College in 1992. He began his career with the company in the Commercial Underwriting Department, where he held various positions, including senior underwriter. In 2005, Paul transitioned to the role of District Manager with the Marketing team. He was promoted to Regional Vice President of Marketing in 2012. Paul returned to the Underwriting Department as Vice President in 2020 and then, the following year, received a promotion to Executive Vice President. In 2026, Paul was promoted to Senior Executive Vice President and Chief Operating Officer. In this role, he leads enterprise operations, including Underwriting, Claims, Marketing, Innovation, Business Intelligence, Digital Experience & Solutions, Reinsurance, and Information & Technology Services. Paul’s extensive leadership experience and risk management knowledge are valued assets not only to The Andover Companies, but also to other organizations he serves, such as Saint Thomas Aquinas High School in Dover, New Hampshire, where he is an active member of the board of trustees.

Stephen “Steve” Randall began his career in the insurance industry in 1980. Since then, he has held numerous executive-level roles at a wide variety of insurance companies, including GE Financial Assurance, Liberty Mutual, and The Hartford. In 2014, he joined The Andover Companies as Vice President and head of the Claims Department. Steve’s responsibilities were expanded in 2019 to include oversight of the Innovation and IT teams, and in 2021, he was promoted to Senior Vice President. Today, Steve serves as Executive Vice President & Chief Claims Officer. He is a graduate of Niagara University, where he earned a Bachelor of Science in Criminal Justice. He is a board member of the Rhode Island Joint Underwriting Association and a former board member of the Electric Insurance Company, the National Insurance Crime Bureau, and the American Arbitration Association.

Amy DiPerna has worked in The Andover Companies Accounting Department since 2010. Amy was promoted from Assistant Vice President and Assistant Treasurer in 2019 to her current role, overseeing the company’s accounting, finance, and billing functions. Prior to joining The Andover Companies, Amy was a manager at PricewaterhouseCoopers LLP, where she specialized in the insurance industry. Amy earned both a Bachelor of Science and a Master of Science in accountancy from Bentley University. She also holds a certificate of taxation and is a Certified Public Accountant (CPA). Amy’s passion for facts and figures and insurance spills over into her extracurricular activities. She serves as the chair of the Audit Committee for Guaranty Fund Management Services and is a member of the board of trustees for the Insurance Library Association of Boston.

Patrick Duchette joined the organization in 2008 after graduating from Bowdoin College with a Bachelor of Arts in economics and government & legal studies, beginning his career on the Personal Lines Underwriting team. Over the past 18 years, Pat has advanced through roles of increasing responsibility, earning a reputation for underwriting discipline, thoughtful leadership, and a collaborative approach. In 2015, he was promoted to Director of Personal Lines Underwriting, where he served as a trusted territory leader and contributor to the company’s underwriting strategy. In 2023, Pat formally joined the Reinsurance team, further broadening his perspective across underwriting and risk management functions. He has also contributed to numerous task forces and product committees, including the company’s AI Task Force, reflecting his forward-looking mindset and commitment to continuous improvement. Today, as Senior Vice President and Chief Underwriting Officer, Pat oversees Personal and Commercial Lines Underwriting, Underwriting Product Development, and Loss Control. He holds the Chartered Property Casualty Underwriter (CPCU) and Associate in Reinsurance (ARe) designations and is a member of the Boston CPCU Chapter Society.

Justin Libbey began his career at The Andover Companies in 2005 as a Personal Lines underwriter. In 2007, he transitioned to the role of a Commercial Lines underwriter. After spending six years in Underwriting, Justin’s knowledge and experience earned him the opportunity to join the Field Department as a special agent responsible for the Central and Western Massachusetts territory. Then, he transitioned to District Manager of the Eastern Massachusetts territory. In 2020, Justin was promoted to Regional Vice President–New England Marketing. The following year, Justin was named Vice President of Field and Marketing, a role that called on him to utilize all the prior skills and capabilities he had developed. Today, he serves as Senior Vice President & Chief Marketing Officer, overseeing the day-to-day operations of The Andover Companies agency partnerships and leading Field Marketing, Field Marketing Services, and Brand Strategy & Communications. Justin joined the company after graduating from Bowdoin College with a Bachelor of Arts in economics. While working at The Andover Companies, he earned a Master of Science in insurance management from Boston University. He is a member of the Boston CPCU Chapter Society.

Kevin McNamara joined The Andover Companies in 2014 as a technology consultant on the Information and Technology Services team. Over the course of his tenure, he has taken on increasingly broad responsibilities and earned several promotions — including to Assistant Vice President of Technology Services, Technology Transformation Information Security Officer, and Vice President of Information and Technology Services. Today, Kevin leads the IT organization as Senior Vice President & Chief Information Officer. In this role, Kevin is focused on driving the company’s technology strategy with the goal of positioning The Andover Companies as a modern digital carrier — one that can efficiently deliver high-quality solutions and support services, create meaningful business value, and effectively manage risk. Prior to joining Andover, Kevin spent a decade at Keurig Green Mountain, where he served as Senior Director of Information Systems & Technology. Kevin earned a Bachelor of Science in information technology from the University of Massachusetts in 2010 and completed the university’s Graduate Certificate Program in Business Administration in 2016.

Kevin Ouellette joined The Andover Companies in December 2020 as Vice President, Secretary & General Counsel and is currently Senior Vice President, Secretary & Chief Legal Officer. He leads the organization’s Human Resources, Facilities Management, and Administration teams. He advises the board of directors on governance, regulatory, and other matters and provides broad legal and regulatory support to the organization. Kevin oversees the management of the organization’s commercial real estate investment properties and participates in the management of the organization’s investment portfolio. He also oversees The Andover Companies Charitable Foundation. Outside The Andover Companies, he enjoys being a board member and chair of the Grants Committee of the Boston Chapter of the Insurance Industry Charitable Foundation. Prior to joining The Andover Companies, Kevin was senior counsel at Wells Fargo Asset Management; senior counsel at Evergreen Investments; and an associate with Ropes & Gray LLP, where he started his legal career after graduating from New York University School of Law. He earned his undergraduate degree in chemistry from Harvard College.