Gary Woolman is the Founder of Woolman Financial Group and a Retirement Income Specialist with WestPoint Financial Group. With more than four decades of experience in the financial services industry, Gary has built a practice rooted in analytical insight, hard work, and a deep commitment to faith and community.
Gary began his career in the late seventies, transitioning from banking into insurance after being encouraged to explore the industry. Since then, he has grown his practice into a trusted resource for business owners, corporate executives, and families. His approach emphasizes helping clients understand their full financial picture and developing strategies tailored to their unique goals and circumstances.
Beyond his professional work, Gary is actively involved in his community and his church. Over the years, he has served in various leadership and ministry roles, including elder, choir member, and worship team singer, and he currently helps lead the Legacy Adult Bible Fellowship at Headwaters Church. He also served on the board of the Discipleship Walk ministry. His professional involvement includes serving as past president of NAIFA-Fort Wayne and NAIFA-Indiana, and in 2025 he was honored with NAIFA-Indiana’s Jack Peckinpaugh Award*, the organization’s highest recognition. He is also a graduate of Leadership Fort Wayne and a member of FINSECA, a national association dedicated to financial security.
Outside of work, Gary enjoys traveling with his wife, Becky, and spending time with their children and six grandchildren. Their shared faith continues to be central to their lives and to their service within their community.
* The Jack Peckinpaugh Award is presented by NAIFA-Indiana to recognize outstanding service and leadership within the association and the community. It is not based on investment performance or client experience and should not be considered a guarantee of future results.
