Experience

With over three decades of experience guiding accomplished families and entrepreneurs, John O’Leary is recognized for his ability to bring clarity and leadership to even the most complex financial situations. As Managing Director and founder of the O’Leary Partners team at UBS Private Wealth Management, John leads with the conviction that exceptional outcomes begin with exceptional understanding—of people, purpose, and possibility.

John’s leadership philosophy is rooted in creativity, collaboration, and precision. He acts as the strategic quarterback for his clients, aligning UBS’s world-class capabilities in asset management, lending, capital strategy, and business transitions to serve each client’s unique goals. His team’s approach is deliberately boutique, yet backed by the strength of UBS’s global platform—serving business owners, founders, senior executives, and medical and legal professionals who seek both partnership and perspective.

Beyond UBS, John serves as President of the Key West Art & Historical Society, where his passion for stewardship and community shines through his commitment to preserving the cultural legacy of the Florida Keys. Featured in Forbes and Research Magazine for his insight and innovation in private wealth management, John embodies a leadership style defined by both strategy and service.

John and his wife, Karen, divide their time between the Northeast Tri-State Area and South Florida, where they maintain a multi-acre grove in the Redlands District cultivating exotic fruits—a reflection of John’s lifelong belief that growth, in every sense, is best nurtured with care and intention.

Christopher earned a Bachelor of Arts from Franklin & Marshall College, majoring in Business Administration with a minor in Economics. He holds his Series 7, 66, 9, 10, and insurance licensing. Christopher joined UBS as a Financial Advisor in 2013 after starting his career with Merrill Lynch Wealth Management. Christopher comes to us from the UBS Wealth Advice Center where he was the Head of Training and Financial Advisor Development. Christopher was responsible for the building of many successful training initiatives, committed to the development and growth of Financial Advisors. 

Christopher has held various positions across UBS, resulting in a deeper understanding of the firm’s resources and capabilities and, more importantly, the needs of clients. Christopher specializes in wealth management strategies that include cash management, advisory solutions, alternative investments, legacy planning, equity awards, mutual fund analysis, and portfolio recommendations. Christopher is a Certified Financial Planner with over a decade of industry experience. He collaborates closely with high-net-worth families to create tailored retirement plans that align with their desired goals.   

Chris, his wife, Katie, and their son, Ethan reside in New Canaan, CT. Chris is passionate about cars and enjoys spending his free time playing golf, skiing, attending car meets, and being outdoors.

As the second generation in the O’Leary Partners family practice at UBS, Gabrielle O’Leary combines deep-rooted legacy with forward-thinking strategy. She partners with business owners, founders, senior executives, and legal and medical professionals—as well as multi-generational families—to simplify complex financial lives and help clients build lasting, purpose-driven wealth.

Known for her warm yet strategic approach, Gabrielle helps clients make confident financial decisions in both stable and shifting market environments. Her expertise spans optimizing portfolios for tax efficiency, managing concentrated equity positions, designing bespoke fixed income sleeves, and providing access to private alternative investment opportunities.

Before joining UBS, Gabrielle worked at J.P. Morgan Asset Management and OppenheimerFunds, where she developed a strong foundation in capital markets, portfolio construction, and investment research. She holds the Certified Investment Management Analyst® (CIMA®) designation through the Investments & Wealth Institute and the University of Chicago Booth School of Business, and the Certified Exit Planning Advisor® (CEPA®) designation, allowing her to support business owners in preparing for and navigating life before and after a sale.

Gabrielle is also the host of O’Leary Partners Observations, a fresh and approachable podcast delivering “aha!” moments that connect personal priorities with financial decision-making. She regularly delivers UBS’s Own Your Worth content, helping women break the cycle of financial abdication and step confidently into their roles as wealth decision-makers.

Deeply invested in the Miami community, Gabrielle is an active member of the Rotary Club of Miami and United Way Miami. She lives in Brickell with her husband, Drew, and their spirited Maltipoo, Pearl. Outside of work, she enjoys exploring new restaurants, cheering on her favorite teams, and staying active with HIIT workouts.

Jake is a Wealth Strategy Associate at UBS who delivers a Ritz-Carlton level of service, ensuring every client experience is seamless, personalized, and top-tier. Wearing multiple hats, he blends financial knowledge, strategic problem-solving, and an unwavering commitment to excellence to help clients navigate their wealth with confidence.

Since joining UBS in 2019 after earning his B.S. in Finance with a minor in Information Technology from Monmouth University, Jake has been a key player in client service and operations. Armed with his SIE, Series 7 & 66 Licenses, he thrives in the fast-paced world of wealth management, bringing the same passion, precision, and competitive mindset he honed as a lifelong sports enthusiast.

A proud resident of Hoboken, NJ with his wife Jillian, Jake is a die-hard sports fan who loves catching games, traveling to new destinations, and playing golf. Whether on the course or in the office, he brings the same dedication and strategy—always looking for the next great opportunity.