Robert Shestack, CVBS, CF2, WBC, HWC is a respected healthcare executive, industry builder, and servant leader with more than four decades of experience shaping the healthcare, insurance, and voluntary benefits landscape. He currently serves as President & Chief Enterprise Actuary of NIH, where he leads financial, actuarial, and strategic initiatives designed to strengthen operational performance and fuel long-term relationships and growth.
In addition, Mr. Shestack serves as Chairman, Chief Executive Officer, and Publisher of the Healthcare & Voluntary Benefits Association (HVBA), an organization he has helped grow into a trusted national platform since 2008, where meaningful relationships are built, innovation is advanced, and business gets done.
Mr. Shestack earned degrees in Actuarial Science, Risk Management, and Business Law from Temple University’s Fox School of Business. His academic foundation, combined with decades of hands-on leadership, has shaped his disciplined yet people-first approach to business. Mr. Shestack is a Certified Financial Fiduciary (CF2), an accredited member of the National Ethics Bureau, and is listed in Madison’s Who’s Who.
Throughout his career, Mr. Shestack has been widely recognized for his impact and integrity. His honors include induction into the International Workplace Benefits Association Hall of Fame and the Health & Voluntary Benefits Association Hall of Fame, the Inaugural Benefits Advisor of the Year, Workplace Benefits Rockstar, and the H. Wayne Snider Distinguished Alumni Award from Temple University’s Fox School of Business. He also holds over 50 professional licenses and certifications and, in 2024, was appointed to the Board of Directors of the National Workplace Violence Safety Association. He is the only industry professional to achieve what is often referred to as the industry’s “trifecta”, two Insurance Halls of Fame while receiving the Benefits Advisor of the Year award.
Public service has always been central to Mr. Shestack’s life. First elected in 1999, he has also served as President of the New Jersey State Association, Board Member of the New Jersey State EMS Council, and Vice Chairman of the First Responder New Jersey Joint Insurance Fund. For more than 25 years of distinguished service, he was formally recognized by the New Jersey State Joint Legislature as the most experienced Fire Commissioner in the history of the Mt. Laurel Fire Department.
Mr. Shestack’s executive leadership experience includes CRO of Juice Financial, Managing Director at Marsh/Mercer, EVP for The AmWINS Group and Co-Founder and President of AmeriFlex, the first third-party administrator to utilize FSA debit card technology for instant claims reimbursement. His areas of expertise span ERISA, IRS, DOL, COBRA, HIPAA, ACA, CAA, OBBBA, FMLA, and IRC Sections 105, 125 and 213(d).
At the heart of Mr. Shestack’s leadership philosophy is an unwavering belief that people come first. He is widely known for building organizations where employees are treated like family—valued, respected, and empowered to grow both professionally and personally. This commitment is reflected in the remarkable tenure of his teams, with many colleagues choosing to work alongside him for 15+ years. Mr. Shestack leads with accountability, trust, and care, fostering a culture where loyalty is earned, voices are heard, and excellence is a shared standard. His ability to balance high performance with genuine compassion has made him not only an exemplary leader, but also a mentor and steward to those who work with him.
