Winged Keel Group (“Winged Keel”) is proud to announce the addition of Christopher “Chris” Cooley, CFP® as a Senior Director and Client Relationship Manager. Based in Nashville, Tennessee, Chris will play a key role in advancing Winged Keel’s strategic expansion in the Southeast and deepen the firm’s ability to partner with institutions and advisors in the region.
Chris joins the firm with more than 30 years of experience in insurance and estate planning. Over his career, he has advised affluent families, business owners, and leading financial institutions, with senior roles at MetLife, TPG Financial, and most recently as the founder of Prosperity Life Advisory Group. Chris is recognized for his expertise in estate planning, business succession, and wealth transfer, as well as his collaborative work with financial institutions to design sophisticated planning solutions. Chris graduated cum laude with a bachelor’s degree in Business Administration and Economics from Berry College in Mount Berry, Georgia.
Joining Chris will be his longtime colleague, Trey Davis, who will join as an Associate Director, Case Design. Trey has two decades of experience preparing tailored insurance and estate planning presentations for wealth advisors and their clients nationwide. A Nashville native and Western Kentucky University alum, Trey’s focus is on insurance solutions for high-net-worth families, senior executives, and entrepreneurs.
“Chris and Trey have worked together for 18 years, and together bring deep expertise, strong relationships, and a genuine commitment to client outcomes that perfectly align with Winged Keel’s values and vision,” said Donna Litke, Managing Director. “Their addition enhances our ability to expand thoughtfully into the Southeast while continuing to deliver sophisticated solutions for institutions nationwide.”
“I’m excited to join Winged Keel’s industry-defining team,” said Cooley. “Winged Keel has set the standard for sophisticated planning, seamless advisor partnerships, and innovative solutions. This platform enables me to bring three decades of experience advising families and institutions into an environment built for scale and precision. I look forward to leveraging my experience to build lasting partnerships and deliver tailored strategies that meet the evolving needs of our clients.”
The addition of Chris and Trey underscores Winged Keel’s continued momentum following its 2025 investment partnership with GTCR, reinforcing the firm’s commitment to scaling its platform, expanding into new markets, and delivering world-class solutions to clients and partners.
About Winged Keel Group
Winged Keel Group is the premier national platform for the structuring, implementation and administration of high-end life insurance solutions. With ten offices nationally, the firm specializes in Traditional Life Insurance, Business Continuation Insurance, Private Placement Life Insurance and Annuities, and Corporate-Owned Life Insurance portfolios. For more information on Winged Keel Group, please visit www.wingedkeel.com.
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Contacts
Barbara Novak
Principal
Winged Keel Group
212.527.8000