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November 9-10, 2021
W Chicago City Center

Ken Masters
Principal at Winged Keel


As a Principal of Winged Keel Group, Ken Masters works closely with a client’s team of advisors to design, model, and implement sophisticated life insurance and Private Placement portfolio strategies. With the technical background required to build dynamic, advanced planning models, and an understanding of the transfer tax system, Ken enjoys being able to communicate complicated concepts and analysis in an understandable way. Prior to joining Winged Keel Group in 2018, Ken served as the Director of Life Insurance Design & Development at Pinnacle Financial Group for eight years. Before that, he held roles directing R&D and advanced case design with two life insurance advisory companies and delivered advanced market consulting services to Sun Life Financial.

Ken is a member of the Boston Estate Planning Council (BEPC), Finseca (formerly the Association for Advanced Life Underwriting), and CFA Society Boston. He has spoken on advanced estate planning techniques at national insurance conferences and has been a guest lecturer for Boston University’s Graduate Tax Law Program. His articles have appeared in National Underwriter magazine, Private Wealth magazine, Estate Planning magazine, the online journal of Trusts & Estates magazine, and LinkedIn’s Pulse, and he has been quoted in various industry publications.

Majoring in Finance, Ken graduated with a Bachelor of Commerce from McGill University’s Desautels Faculty of Management. He is also a CFA® Charterholder, Chartered Life Underwriter®, Chartered Financial Consultant®, and Accredited Estate Planner®, and holds FINRA Series 7, 24, and 66 securities licenses.
Ken and his family live in Medfield, Massachusetts. In addition to spending time with his family, Ken enjoys playing golf, practicing martial arts, and studying history.

Agenda Sessions

  • Modernizing estate planning with PPLI

  • Roundtable discussions