We Are The Andover Companies

Charles “Chuck” DiGrande has spent the entirety of his 31-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 CEO. 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 this role, he oversees the Personal Lines Underwriting and Commercial Lines Underwriting teams and is responsible for directing the company’s reinsurance, business intelligence, and loss control strategies. 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. Steve 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 as vice president and treasurer, 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.

Kevin Ouellette joined The Andover Companies in December 2020 as vice president, providing strong leadership to the company’s Human Resources, Facilities Management, and all administrative teams. Kevin also serves as The Andover Companies general counsel and secretary, with broad responsibilities that include supporting and advising the board of directors on governance and regulatory matters, as well as contract reviews and negotiations. Additionally, Kevin oversees the management of the company’s commercial real estate investment properties and The Andover Companies Charitable Foundation. Kevin also enjoys being a board member of the Insurance Industry Charitable Foundation Boston Chapter. 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 career after graduating from New York University School of Law. He earned his undergraduate degree in chemistry from Harvard College.

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 calls on him to utilize all the prior skills and capabilities he has developed. One of Justin’s most critical duties as vice president is to oversee the day-to-day operations of The Andover Companies agency partnerships. In addition, he is responsible for field support, strategy and business development, and marketing. 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 for the Information and Technology Services team. Since then, his responsibilities have continued to expand and he has earned several promotions, including to assistant vice president of Technology Services and technology transformation information security officer. Today, Kevin leads the IT team as vice president of Information and Technology Services. He is primarily focused on driving the company’s technology strategy, which aims to ensure that The Andover Companies is a modern digital carrier that can efficiently deliver high-quality solutions and support services, create business value, and manage risk. Kevin’s previous work experience includes a 10-year stint at Keurig Green Mountain, where he served as senior director of Information Systems & Technology. Kevin is an AWS Certified Associate Architect and AWS Certified Cloud Practitioner. He graduated from the University of Massachusetts with a bachelor of science in information technology in 2010 and completed the school’s graduate certificate program in business administration in 2016.