Our Leaders

Steve Gregory

President of Employee Benefits | Executive Partner

Steve Gregory serves as the President of Employee Benefits and leads Shepherd’s  Benefits division. He is called upon for his expertise in financial evaluation, benefit design and implementation of risk management strategies for employer-sponsored health and wellness plans. Additionally, he performs insurance contract analysis, vendor assessment, claims analysis and overall plan reviews.


With over 26 years of experience in the insurance industry, Steve is engaged as a public speaker on issues relating to healthcare reform, alternate funding strategies and the employee benefits landscape. In addition to his time at Shepherd, Steve serves on the Board of Directors for Prevail, Inc.


Steve is a graduate of Indiana University and is married with two daughters. During his free time, he loves being with his family, skiing, and competing in triathlons.

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