Navigating strategy, innovation and growth at the Captive Review Conference USA 2026

Senior leaders from across the captive insurance ecosystem will gather in Chicago on June 9–10 for the highly anticipated Captive Review Conference USA 2026.

Held at the Union League Club of Chicago, this flagship event provides a vital platform for executives responsible for risk, finance and insurance strategy to examine the trends, challenges and opportunities shaping the captive insurance market.

The captive insurance sector is at a pivotal juncture. As organisations face increasing volatility, regulatory scrutiny and emerging risks, from cyber and climate to healthcare and supply chain disruption, captives are playing an increasingly strategic role in risk financing. Businesses are rethinking how they structure, capitalise and deploy captives to enhance resilience, unlock value and support long-term growth.

Building on insights from across the industry, Captive Review Conference USA 2026 will deliver two days of in-depth discussion, practical case studies and expert analysis. Attendees will hear from leading practitioners and advisors as they explore how captives can evolve to meet the demands of a rapidly changing risk landscape.

The conference agenda covers a wide range of critical topics, including strategic reviews, capital modelling, tax and regulatory developments, talent and AI, reinsurance optimisation, medical stop-loss, voluntary benefits, cyber risk, parametric solutions and emerging captive use cases.

Across keynote sessions, panel discussions and dual-track streams, participants will gain actionable insights into both foundational and advanced captive strategies, from “Captive 101” guidance on structuring and partner selection to sophisticated approaches in financial optimisation, analytics and innovation.

Delegates will benefit from:

• Exclusive networking with senior captive owners, risk managers and industry advisors.
• A comprehensive agenda covering the most pressing challenges and opportunities in the captive market.
• Insights from across the ecosystem, including regulators, consultants, actuaries and corporate risk leaders.
• Practical case studies and real-world applications to support strategic decision-making.
• A collaborative environment to exchange ideas and build valuable industry connections.
• A prime location in Chicago, a key hub for corporate risk and insurance leadership.

Key speakers include:

• Theresa Severson – Senior Vice President – Insurance & Risk Management, Kite Realty Group
• Nancy Gray – Regional Managing Director – Captive & Insurance Management, Aon
• Mike Meehan – Principal, Milliman
• Anne Marie Towle – CEO - Consulting, Hylant
• Peter Carter – Head of Climate Practice & Head of Captive & Insurance Management Solutions, WTW
• Peter Kranz – Senior Vice President, Director, Alliant Insurance
• Heather McClure – Managing Partner, General Counsel, Helio Risk
• Jim Knutson – Business Development Manager, Employer's Coalition on Health
• Kris Miller – VP, Treasurer, Lithia Motors
• Jack Meskunas – Executive Director – Investments, Oppenheimer & Co Inc.
• Eryn Brasovan – Partner, Womble Bond Dickinson
• Kristen Lawler – Insurance Tax Partner, Crowe

Here’s what some of the industry-leading executives attending the event said:

"One of the biggest challenges will continue to be regulatory and tax scrutiny. As captives become more widely used and more sophisticated, regulators and tax authorities are taking a closer look at structures and ensuring they reflect real insurance and sound risk management." – Kristen Lawler, Insurance Tax Partner, Crowe

"In my view the biggest challenge will be incoming talent. While the industry has made progress in developing education pathways, we are still behind in balancing new talent entering the market with those retiring." – Mikhail Raybshteyn, Insurance and Risk Management Strategic Tax Advisor

"Because the insurance market is often slow to respond to emerging risks, captives present a significant opportunity for organisations to take a more proactive and strategic approach—retaining risk, accessing capacity and even turning insurance into a profit centre." – Braedy Walker, Senior Vice President, Platform Insurance

Alex Hackett, Senior Conference Organiser, Captive Review & Intelligent Insurer, said:

"We are excited to bring together leading voices from across the captive ecosystem at this year’s conference. As captives continue to evolve into a core strategic tool for organisations, this event will provide the insights, connections and practical guidance needed to help risk leaders maximise their captive’s value and prepare for the future."

The event will also explore how organisations can future-proof their captive strategies through better use of data, analytics and actuarial insight, as well as how captives are expanding into new areas such as employee benefits, parametric insurance and emerging risk classes.

Featuring expert-led sessions across two days, the conference combines keynote presentations, panel debates and interactive discussions designed to equip attendees with the tools and knowledge needed to maximise the value of their captive programmes.

Run by Captive Review, a leading source of insight and analysis for the global captive insurance market, the event brings together the industry’s most influential voices to share expertise, challenge thinking and drive innovation.

For more information and to secure your place, visit Captive Review Conference USA 2026

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