As Executive Vice President and Insurance Specialist, Miles Fleming supports Lumena’s operational success while helping clients navigate Medicare, healthcare coverage, and retirement-related insurance decisions.
Miles joined Lumena Financial Strategies in 2015 after retiring from a thirty-year career as an executive in the technology industry. The move was a deliberate one. After decades in corporate leadership, he wanted a role that would let him have a more personal and meaningful impact on the people he served.
As Executive Vice President, he oversees Lumena’s back-office operations including payroll and vendor relationships while also providing technical support for our team.
Miles’ personal experience with aging parents and disabled loved ones led to his passion for helping clients navigate the confusing landscape of health benefits. After discovering the difficulty in establishing care, filling out all the right forms, and interacting with social workers, he decided that he could help families by providing education and resources.
In his role as the firm’s Insurance Specialist, he focuses particularly on healthcare for seniors. Both individually and as a featured speaker in our webinar series, he educates clients about managing healthcare expenses in retirement, Medicare eligibility and enrollment, and the various private insurance options that work alongside Medicare. Healthcare is deeply personal, whether a client is managing a serious illness, adjusting to the loss of a trusted doctor, or planning for long-term care. He takes the time to understand each client’s specific needs and align them with the appropriate coverage.
Beyond his work at the firm, he has served on the boards of the San Diego Council on Aging, which advocates for quality of life for seniors, and Arts for Learning San Diego, which provides arts education to schools with limited public funding. He is an active member of Rotary, a Paul Harris Fellow, and a volunteer with Hope without Boundaries outreach in Mexico.
He holds a bachelor’s degree in music from UCLA.
His personal experiences as a caregiver continue to shape the way he works with clients, combining practical knowledge with a genuine desire to help families navigate important healthcare and insurance decisions.