Strategic Insight for Oklahoma’s Visionary Leaders
For Oklahoma’s visionary leaders, the challenge is scaling with intention while navigating a complex economic landscape. The Signature Speaker Series to bring together a thoughtfully assembled group owners and executives to explore the real financial and operational pressures of 2026 and beyond.
The Series provides both the expertise and the forum for meaningful discussion. These quarterly sessions offer space for strategic clarity and relationship‑driven dialogue among peers facing similar responsibilities. Each experience reflects the Watermark standard—intentional, considered, and designed for those carrying meaningful responsibility.
Captive Town Hall: Risk Ownership & Captive Insurance Strategy
Moderated by Jason Willeford, Dillingham Insurance with panelists Chad Dillingham, Dillingham Insurance; Blake Kerr, Helio Risk; Steven Kinion, Oklahoma Insurance Department
August 25, 2026 | 9:00 to 10:30 a.m.
The Lively | Oklahoma City
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This panel will focus on three core questions. Why are sophisticated companies increasingly choosing to retain and finance their own risk rather than transfer it through traditional insurance. What does it actually take, operationally and financially, to become a strong candidate for a captive. And what is Oklahoma's role as a leading, well-regulated domicile for this strategy.
The conversation will consider captive insurance as both a risk management tool and a financial planning strategy for owners and executives managing complex operations, with particular attention to what the path to implementation looks like in practice and what conditions make a business a genuine candidate.
For questions regarding the Signature Series, please contact marketing@watermark.bank.
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