Robert S. Shestack

Robert S. Shestack

Chairman & CEO

Voluntary Benefits Association

Rob Shestack is the Chairman and CEO and Hall of Fame member of the Voluntary Benefits Association, the first national non-profit trade association focused on Voluntary Benefits for employer groups and affinity groups. Our goal is to promote the education, implementation, product development, technology and enrollment of Voluntary Benefits in the workplace. 

Mr. Shestack was the former EVP and National Practice Leader for The AmWINS Group, the largest insurance wholesaler in the United States, placing over $12 billion in annual premium. In his role he was responsible for all carrier relations, enrollment & implementation activity and communications, as well as the execution of the 5-year strategic business plan. Prior to joining AmWINS, Mr. Shestack was Managing Director and National Sales Leader of Corporate Benefits at Marsh & McLennan. Mr. Shestack’s experience working with voluntary benefits includes product development, insurer relations, strategic innovation, communication & enrollment strategies.

Mr. Shestack has been responsible for managing and developing high level sales talent and establishing client and partner relationships in the employer benefits arena. A 30+ year industry veteran, Mr. Shestack holds a Workplace Benefits Consultant certification, a Certified Voluntary Benefits Specialist designation as well as a degree in Actuarial Science. Also, he is certified in Health & Welfare and Cafeteria Plan Fundamentals through the American Academy of Actuaries. He is a Risk Management Capstone Course student advisor at Temple University’s Fox School of Business, his alma mater, where he and his wife have a $10,000 scholarship program for the Fox School of Business and Temple University.

In addition to his responsibilities at the VBA, Rob was also inducted into the Workplace Benefits Hall of Fame in July 2010, joining an elite group of voluntary benefit industry leaders. An accomplished author published in over 100 articles and white papers as well as an accomplished speaker, he wrote a chapter on critical illness in the 2008 book “Workplace Marketing — A Promise to Deliver” and is working on his next 2 books.

Mr. Shestack was featured as the cover story for Benefits Selling magazine in 2007 and he received the inagural Voluntary Benefits Adviser of the Year award in 2011. The award recognizes outstanding service to group benefit plan sponsors by brokers and advisers, as well as overall contributions to the profession. In April 2013, he was honored with the prestigious H. Wayne Snider Distinguished Alumni Award from Temple University’s Fox School of Business recognizing Rob as someone who has distinguished himself or herself for at least 20 years in the field of Insurance, Risk Management and Actuarial Science.