Insurance Operator
Turned Specialist.
Ryan Headley brings over two decades of hands-on insurance industry experience to every engagement — not as a distant consultant, but as someone who has lived every side of the operation.
A graduate of Sierra Academy of Aeronautics (with studies at San Jose State University), Ryan began his career as Director of Flight Operations at Sierra Academy — a role that demanded rigorous systems thinking and operational precision. That foundation proved invaluable when he transitioned into the insurance industry in 2003.
Early in his insurance career, Ryan honed his skills on the sales side — developing a producer's instinct for client needs and relationship-building that would inform every operational decision he made as a leader.
As a Partner at Stratton Agency in San Carlos, CA, Ryan helped build and lead an independent insurance agency — navigating the daily realities of client relationships, staff management, carrier negotiations, and the technology that holds it all together. When the agency was sold to PCF Insurance in 2018, it was a testament to what the team built together.
Following the sale, Ryan moved into specialized consulting, focusing on the Applied Epic management system — the platform most agencies rely on and few fully leverage. That expertise eventually led to founding Epic Optimizer as a dedicated practice built around one discipline done exceptionally well.