Name: Chelsea Maeda
Firm: Winged Keel Group
Location: New York, NY
Total Value of Policies: $105 Billion
Background: Chelsea Maeda was born and raised in Hawaii, the youngest of three children. After attending Columbia University, where she studied statistics and music, she interned at Winged Keel and joined the firm full-time in 2008. “I never expected to end up on the sales side,” she says. “But I saw the impact we were having and wanted to stay.” She rotated through analytics and design roles before moving into a client-facing position in 2012. In 2020, she became a principal and joined the firm’s executive management committee.
Building Relationships: Maeda works with high-net-worth clients, focusing on business continuity planning and private placement life insurance. “We help protect key executives whose absence could materially impact their company,” she says. In the private placement space, she helps clients use life insurance as a tool for tax-efficient investing. Much of her role now involves partnering with financial advisors at institutions and wirehouses to help them integrate life insurance products into broader client strategies.
Competitive Edge: Maeda credits her team and firmwide infrastructure as key differentiators. “Life insurance is often one of the longest-held assets a client owns,” she says. “We’ve built a platform that can service those policies far into the future.” She also points to the meaning behind the firm’s name. “A winged keel stabilizes a sailboat from below,” she says. “That’s how we see our role—providing strength behind the scenes.”
Investment Philosophy/Strategy: “Education is central to everything we do,” says Maeda. “There are long conversations—often with multiple deep dives—to help clients understand how these products work.” She says her background in statistics helps her explain the pricing and structure of insurance products in a transparent way. “I walk clients through every fee and charge,” she says. “It’s about making the product understandable and aligned to their specific goals.”
Best Advice: “Character, competence, and commitment,” she says. “Do what’s right even when no one is looking.” And to clients who ask how much insurance they need? “Enough that you can sleep at night knowing your family is protected—not more than you’re comfortable with,” says Maeda. “That’s the right number.”
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