October 29, 2026 | Hartford Marriott Downtown, Hartford, CT
Rewriting Risk in an Era of Uncertainty
ITF 2026 Bios
Prem Sagar Sundaram
CLIENT PARTNER
Cognizant
Prem is a Client Partner supporting a leading insurance client. He has driven large-scale business transformation initiatives across the insurance value chain, with a strong focus on Engineering, AI, Automation, and Strategy. Passionate about turning business vision into meaningful outcomes through innovation and people leadership, he operates at the intersection of what he calls “The Man, the Machine and the Digital Mind.” Outside of work, Prem is an avid runner and recently achieved a personal best of 1:57 minutes at the Hartford Half Marathon.
Panel One: AI in Insurance: Risk vs. Reward
Josh Hershman
COMMISSIONER
Connecticut Insurance Department
Josh Hershman was nominated by Governor Ned Lamont to serve as Connecticut’s 34th Insurance Commissioner, leading a department with regulatory oversight of one of the largest and most complex insurance markets in the nation.
Hershman brings a combination of regulatory leadership, carrier-building experience, and data-driven policy expertise to the role. He previously served as Chief Executive Officer of the Immigrant Life Insurance Company of America, a Connecticut-domiciled and wholly owned subsidiary of IDT Corporation, where he helped build an admitted-market life insurance carrier designed to close coverage gaps for immigrant families.
Hershman also served as Executive Director of openIDL, a Linux Foundation project focused on modernizing insurance data exchange through the development of open data standards. In that role, he worked closely with regulators, insurers, and technology organizations to advance secure, transparent, and efficient regulatory data infrastructure. He has additionally advised organizations across the insurance sector on regulatory compliance, legal risk, and operational strategy, and has been invited to speak nationally on the intersection of insurance and artificial intelligence.
From 2019 to 2022, Hershman served as Deputy Commissioner and Chief Operating Officer of the Connecticut Insurance Department, where he led efforts to modernize internal operations, strengthen regulatory processes, and support responsible innovation within the insurance market. His work during this period focused on improving execution discipline, expanding the Department’s analytical capabilities, and positioning the agency to supervise increasingly complex insurance products and business models.
Earlier in his career, Hershman practiced law with a focus on complex business planning and litigation, advising clients operating in highly regulated environments.
Hershman is a long-serving member of the Guilford Fire Commission. He lives in Guilford with his wife and their three daughters.
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.
Brian Zachry, Ph.D
SENIOR DIRECTOR, CATASTROPHE RISK MANAGEMENT
Travelers
Brian Zachry, Ph.D., is a Senior Director in Catastrophe Risk Management for Travelers. This enterprise team is responsible for the evaluation of risk and partners with business units to develop pricing and underwriting strategies related to catastrophes. Dr. Zachry is the enterprise Lead for the Flood Peril and has more than 15 years of catastrophe modeling, hurricane forecasting, and risk evaluation experience.
Dr. Zachry joined Travelers 5 years ago from NOAA, where he held various positions of increasing responsibility at the National Hurricane Center (NHC) in Miami, Florida. His most recent role was Chief of the Technology and Science Branch. In addition to Public Service, Dr. Zachry was a Principal Scientist at Berkshire Hathaway Specialty Insurance and Atmospheric Scientist for Verisk Catastrophe Risk Solutions.
Dr. Zachry holds a doctoral degree in Wind Science and Engineering from Texas Tech University and a Bachelor of Science degree in Atmospheric Science from Florida Institute of Technology.
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
Tisa Rabun-Marshall
HEAD OF MARKETING
Nassau Financial Group
Tisa Rabun-Marshall is a native of Seattle, WA, and now calls Glastonbury, CT home, where she lives with her daughter. As Head of Marketing at Nassau Financial Group, she leads with vision and creativity, driving the brand, shaping marketing strategy, and strengthening agent engagement — all core to accelerating Nassau’s growth. Since joining the company in 2004, she’s navigated a wide range of roles — from Corporate Communications and Community Relations to New Business, Life and Annuity Distribution, and even Dev Ops — making her a rare blend of strategist, storyteller, and operator-proving there’s nothing she can’t do.
Outside of work, she channels that same energy into the Hartford community. Her leadership and time have supported organizations like Leadership Greater Hartford, Hartford’s Camp Courant, United Way – Women United, The Amistad Center for Art & Culture, Hartford Public Library, Girls for Technology and others— all aligned with her deep commitment to youth, the arts, and financial access.
When she’s not elevating brands or creating impact, she enjoys traveling, experimenting in the kitchen, hosting unforgettable gatherings, spending time with family and friends and being a proud mom.
A double alumna of Hampton University, she holds both a Bachelor of Science and an MBA, and is an active member of Alpha Kappa Alpha Sorority, Inc. and the Greater Hartford Chapter of Jack and Jill of America, Inc.
Michael T. Caljouw
COMMISSIONER
Massachusetts Division of Insurance
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.
Mark Meador
PRESIDENT
ConnectiCare
Mark Meador serves as President of ConnectiCare, one of Connecticut's leading health plans, where he leads the organization's mission to make Connecticut a healthier place to live. Since assuming the role in 2023, he has guided ConnectiCare's strategic focus on delivering high-quality, affordable healthcare for the communities it serves.
Before becoming President, Mark served as ConnectiCare's General Counsel from 2019. He is an experienced business leader with extensive expertise across the health, life, and disability insurance sectors, both in Connecticut and nationally.
Mark is actively involved in advancing the health and well-being of Connecticut residents through his service on several nonprofit and business boards. He serves on the boards of the MetroHartford Alliance and The Governor's Prevention Partnership and is Chair of CT IFS.
A graduate of Emory University, Mark earned a Bachelor of Arts in Economics and later received his Juris Doctor from the Emory University School of Law. He and his wife, Christina, live in Avon, Connecticut, with their three children.
Susan Winkler
EXECUTIVE DIRECTOR AND VICE PRESIDENT
Connecticut Insurance and Financial Services (CT IFS) and MetroHartford Alliance
Ms. Winkler represents the workforce and business interests of 23 national and global insurance and financial services [IFS] companies in Connecticut, including P&C, life/retirement, and health insurers, financial services companies and service providers. Ms. Winkler provides strategic direction to a Board of Directors including public-private, high-priority projects of workforce development and business recruitment to bring net new jobs to the Insurance Capital of the U.S. Her work recently led to an international partnership between Connecticut and the U.K. to build insurtech solutions for the insurance industry.
Ms. Winkler resides on numerous Boards and acts as an advisor for many local academic institutions. She is especially fond of her work as the co-founder and current Board member of Northside Institutions Neighborhood Alliance (NINA) in Hartford, CT. For 20 years, this non-profit has renovated blighted properties in Hartford’s historic Asylum Hill neighborhood providing beautifully restored Victoria-era homes and homeownership opportunities to many Hartford residents.
Ms. Winkler received her B.A. from Central Connecticut State University and has a Business Masters Certificate from the UConn’s School of Business.
Most importantly, Susan is active in faith and considers herself blessed in life. She has been married 40 years to her best friend, has three children and four grandchildren.
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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