Robert D. Oros

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Bob is a transformational executive advisor with over 25 years of experience leading growth, profitability, and large-scale business transformations across financial services, M&A, and technology. As Chairman and CEO of Hightower Advisors - one of the fastest-growing advisory firms in the U.S.- he has overseen 54 acquisitions, driven revenue growth of 337%, boosted EBITDA by 545%, and expanded assets under administration from $57B to $1.8T.

Bob is recognized for his authentic leadership style, grounded in transparency, accountability, and innovation. He has spearheaded cultural and operational initiatives such as “The Hightower Way,” the “HIGHFlex” Model, and leadership development programs that have strengthened engagement and cultivated the next generation of industry leaders.

Prior to Hightower, Bob held senior executive roles at HD Vest Financial Services and Fidelity Investments, where he modernized advisor technology, improved productivity, and led the RIA division to a 31% revenue increase. Beyond financial services, he co-founded Reklis Brewing Company, expanding its market presence and operations.

Bob’s contributions have earned him recognition as a two-time Titan 100 honoree and EY Entrepreneur of the Year Midwest Finalist. He holds an honorary Doctorate in Business Administration from Central Michigan University, is a Fellow in the University of Chicago’s Leadership and Society Initiative, and is a frequent industry speaker and advisor.