October 29, 2026 | Hartford Marriott Downtown, Hartford, CT
Insuring The Future
Rewriting Risk in an Era of Uncertainty
ITF 2026 Bios
Panel One: AI in Insurance: Risk vs. Reward
Beth Dwyer
SUPERINTENDENT OF INSURANCE
Rhode Island Department of Business Regulation
Beth Dwyer was appointed Superintendent of Insurance on Jan. 11, 2016, and named Director of Business Regulation in May 2023. Prior to this appointment, she had been employed by the Rhode Island Department of Business Regulation for 15 years as General Counsel and Associate Director. Prior to government service, Director Dwyer was engaged in private law practice in California and Rhode Island.
Director Dwyer is a member of the National Association of Insurance Commissioners (NAIC) and is the current President-Elect of the organization. She has served as chair of the NAIC Property and Casualty (C), Financial Condition (E) and Financial Regulation Standards and Accreditation (F) Committees as well as numerous task forces and working groups. She has served on the Board of Directors of National Insurance Producer Registry (NIPR) and as an Officer of the Interstate Insurance Product Regulation Commissioner (IIPRC). She is the NAIC representative to the Financial Stability Oversight Counsel (FSOC). She is also a member of the Executive Committee of the International Association of Insurance Supervisors (IAIS).
Director Dwyer is a past president of the Rhode Island Women’s Bar Association and was awarded the 2010 Rhode Island Attorney General’s Justice Award for Consumer Protection. She was also the recipient of the 2023 Raymond G. Farmer Award for Exceptional Leadership from the NAIC. She holds the designations of Chartered Property Casualty Underwriter (CPCU), Chartered Life Underwriter (CLU) and Senior Professional in Insurance Regulation (SPIR). She earned a JD from Pepperdine University and a BA from Providence College.
Timothy “Tim” J. Zeilman
GLOBAL HEAD OF PRODUCT OWNERSHIP
HSB
Tim Zeilman is the Global Head of Product Ownership at HSB, a member of Munich Re’s Risk Solutions family since 2009.
In his role as HSB’s Global Head of Product Ownership, Tim is responsible for HSB’s major insurance products including Equipment Breakdown, Service Line, and Cyber. Tim also participates in new product initiatives including the development of insurance product concepts covering emerging artificial intelligence exposure.
Prior to taking his current position, he worked in HSB’s new products group, as an attorney in HSB’s Law Department, and as HSB’s Global Product Owner for Cyber.
Tim holds a Bachelor of Arts degree from Dartmouth College and a Juris Doctor degree from George Washington University.
Jennifer “Jen” Crutchfield
GENERAL COUNSEL AND HEAD OF GOVERNMENT AFFAIRS
Clearcover and Dearborn Labs
Jennifer “Jen” Crutchfield is General Counsel and Head of Government Affairs at Clearcover and Dearborn Labs, where she leads the company’s legal and compliance functions and advises on business strategy, regulatory affairs and corporate governance. She brings more than 15 years of insurance industry experience, spanning large, established carriers and the realities of building and growing an insurtech.
Jen’s work sits at the intersection of insurance, technology and regulation, including the practical challenges of AI governance, product development and bringing new ideas to a highly regulated industry. Before joining Clearcover, she held senior legal and compliance roles in the insurance industry and began her insurance legal career as claim litigation counsel at State Farm.
Jen also helped found the Insurtech Coalition to give insurtech companies a stronger voice in the industry. She likes tackling the messy questions that come with building something new, making complicated issues easier to understand and helping teams get good ideas off the ground.
A native Arizonan, Jen earned her law degree from the University of Arizona.
Craig Weber
HEAD OF INSURANCE STRATEGY
Cognizant
Craig Weber is head of insurance strategy for Cognizant. He leads a team responsible for Cognizant’s insurance offerings, and frequently speaks and publishes on technology topics.
His long-term “passion project” is helping industry players and insurance consumers understand the immense value the industry delivers to society. In support of this goal, Craig has spent his career advocating for holistic modernization approaches that allow the industry to prosper and evolve.
Prior to Cognizant, Craig was CEO of Celent, a well-known analyst firm focused in financial services technology. In that role, he not only led the firm but also served as one of its principal insurance analysts and thought leaders. As an analyst, Craig authored dozens of reports and articles on core systems, modernization, operations, and the evolution of customer experience.
He began his career as a management consultant working for a Boston-based life and annuity carrier. He currently lives in Helotes, TX.
Panel Two: Affordability and Availability: Building Trust in a Changing Risk Landscape
David “D.J.” Bettencourt
COMMISSIONER
New Hampshire Insurance Department
D.J. Bettencourt, formerly the Deputy Commissioner of the New Hampshire Insurance Department, assumed the role of Commissioner after being nominated by Governor Chris T. Sununu and confirmed by the Executive Council in September 2023. He initially joined the department as Deputy Commissioner upon his nomination by the Commissioner in January 2021. Prior to his tenure as Deputy Commissioner, Bettencourt held the position of Governor Sununu's Policy Director for a span of four years, during which he also served as the Governor's liaison to the Insurance Department.
In January of 2026, Commissioner Bettencourt was elected Vice Chair of the National Association of Insurance Commissioners (NAIC) “Northeast Zone”, one of the organization’s four geographic zones. The Northeast Zone is comprised of insurance commissioners from New England and Mid-Atlantic states and serves as a leadership body within the NAIC, coordinating regional regulatory priorities and helping shape national policy initiatives. Commissioner Bettencourt assumed the role of Chairman in February of 2026.
Before his time in the Governor's Office, Commissioner Bettencourt had a distinguished eight-year career (2004-2012) in the New Hampshire House of Representatives, including a two-year term as Majority Leader. Throughout his legislative service, he played a pivotal role in shaping policies that had a significant impact on the insurance industry.
Bettencourt holds a Juris Doctor (J.D.) degree from the University of New Hampshire School of Law, along with a Bachelor of Arts in Political Science and Communications from the University of New Hampshire.
Kim Bishop
ECONOMIC DEVELOPMENT COORDINATOR
CRCOG
Kim Bishop is the Economic Development Coordinator at CRCOG. Prior to joining CRCOG, she supported regional economic development as Chief Talent Officer at the MetroHartford Alliance. Passionate about strengthening communities, Kim brings more than a decade of experience working with municipalities, workforce partners, talent, and businesses to foster a thriving and equitable regional economy.
Kim earned a degree in Human Development and Family Studies from the University of Connecticut. Outside of work, she enjoys spending time with her husband and two sons, reading, and attending live music events.
Representative TBA
TBA
Travelers
TBA
Francis Bouchard
MANAGING DIRECTOR, CLIMATE RISK & RESILIENCE
Marsh McLennan
Francis Bouchard serves as Managing Director for Climate for Marsh Agency’s Private Client Services unit where he with the unit business leaders to craft and deliver climate related solutions for clients, communities and other stakeholders. An active voice on insurance and resilience topics, Bouchard recently served as the 2024 Climate Leader in Residence at Duke University’s Nicholas Institute for Energy, Environment and Sustainability, and serves on APCO Worldwide’s International Advisory Council.
Prior to joining Marsh McLennan, Francis spent 20+ years in a variety of external facing roles with Zurich Insurance Group, most recently as the Group Head of Public Affairs & Sustainability, where he focused on aligning the Group’s government affairs, sustainability and Foundation activities around impactful public affairs and social impact campaigns.
He also formerly chaired the Board of Directors for the national resilience non-profit SBP (now known as StrongWard), serves on the Advisory Board of the climate-focused insurtech incubator InnSure, and is a member of the Advisory Council of the Syracuse University Dynamic Sustainability Lab. He is a graduate of Syracuse University and the George Mason School of Law.
Panel Three: Healthy, Wealthy, and Wise: Adapting to Evolving Consumer Needs
Tom Buckingham
PRESIDENT, INSURANCE
Nassau Financial Group
TBA
Michael T. Caljouw
COMMISSIONER
Massachusetts Insurance Department
Michael T. Caljouw is the Massachusetts Commissioner of Insurance, appointed by Governor Healey. As Commissioner, he oversees the Massachusetts insurance market, an approximately $80 billion industry that ranks near the top ten largest markets in the country and 27th globally.
Commissioner Caljouw is deeply committed to ensuring stable, affordable, and transparent insurance markets and safeguarding consumer interests. He is Vice Chair of the National Association of Insurance Commissioners Financial Condition (E) Committee, the forum for solvency and financial analysis. Commissioner Caljouw also serves on the Financial Regulation Standards and Accreditation (F) Committee, is Secretary of the Northeast Zone and Secretary/Treasurer of the National Insurance Producer Registry. He is a Commissioner on the Massachusetts Health Policy Commission, serves on the Board of the Massachusetts Health Connector and leads the Payment and Pricing Committee of the Affordability Working Group.
Commissioner Caljouw brings over three decades of public and private experience to his current role, including overseeing the policy, regulatory, contracts, and implementation divisions of Massachusetts’ largest health insurance company. In his prior government service, he oversaw several state agencies, developing detailed policy solutions to emerging problems, including solvency and cost containment issues.
Raised in Boston, Commissioner Caljouw graduated from Boston Latin School, Williams College and Suffolk University Law School, serving on the Law Review and earning his Juris Doctorate cum laude. He has taught at Boston University School of Law and is a frequent lecturer on insurance and policy issues. He is the Chair of the Rappaport Center for Law and Public Policy’s Board of Advisors. He is an active mentor to future leaders interested in public policy.
Commissioner Caljouw has received the Better Government Award, Suffolk University Law School’s Outstanding Alumni Service Award and the Arthritis Foundation’s Community Warrior Award. He and his wife Ann-Margaret reside in Boston.
What is Insuring the Future?
Connecticut Insurance & Financial Services (CT IFS) and the Connecticut Insurance Department (CID) are co-hosting the third annual Insuring the Future summit. Insuring the Future convenes insurance executives, regulators, and thought leaders as the industry addresses artificial intelligence, affordability pressures, evolving health trends, and other emerging global challenges reshaping the risk landscape.
Hosted in Hartford, Connecticut, the Insurance Capital of the World, this annual summit provides insider access to forward-looking risk mitigation strategies, responsible innovation, and collaborative regulatory approaches that are defining the future of insurance.
This year’s program expands the conversation around today’s landscape of uncertainty, exploring how the insurance industry is responding to an increasingly interconnected set of challenges, including artificial intelligence, cybersecurity, shifting health trends, market volatility, and evolving consumer expectations.
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