Drew Osborne, CEO of Windward, is passionate about problem-solving and guiding families toward lasting legacies. With years of income tax experience, he integrates tax minimization into every plan, helping clients make smart, simple decisions that support long-term goals. Drew believes in clarity over complexity, preferring straightforward strategies that avoid costly mistakes. His greatest satisfaction comes from helping clients align their money with what matters most. Family is his deepest motivation—whether spending time with his wife and kids or planning memory-making vacations, he values experiences far above possessions. Drew is also active in his community through Young Life and Jacob’s Well Church. At Windward, he leads with vision, teamwork, and a focus on clients’ futures. Energized by the firm’s growth and innovation, Drew looks forward to building Windward’s impact for generations to come. For him, every plan is about more than numbers, it’s about family, purpose, and legacy.