Gary Milwit
About Gary Milwit
Gary Milwit is the Executive Director of Learning & Organizational Development and Talent Acquisition at J.G. Wentworth, with a notable career in sales and organizational leadership. He has held various leadership roles, including President and COO at Stone Street Capital, and has extensive experience in building high-performing sales teams.
Current Role at JG Wentworth
Gary Milwit serves as the Executive Director of Learning & Organizational Development and Talent Acquisition at J.G. Wentworth. He has held this position since 2019, contributing to the Washington D.C. Metro Area. In this role, he focuses on enhancing organizational capabilities and talent management strategies.
Previous Experience at Stone Street Capital
Milwit worked at Stone Street Capital for a total of 13 years. He served as President and Chief Operating Officer from 2016 to 2019, and prior to that, he was the Senior Vice President of Sales and Business Development from 2006 to 2016. His time at Stone Street Capital was marked by leadership in sales and operational strategies.
Background in Education
Milwit studied at the University of Maryland, where he earned a Bachelor of Science degree in Management and Consumer Studies from 1985 to 1989. He also pursued studies in Industrial Technology at the same university from 1990 to 1992. Additionally, he completed a certification in Educational Leadership and Administration at Johns Hopkins University.
Experience in Education Sector
Before transitioning to the corporate sector, Milwit worked in education for a decade at Montgomery County Public Schools. He held roles as an Athletic Director, Coach, and Teacher from 1990 to 2000, contributing to student development and athletic programs.
Sales Leadership and Team Building Expertise
Milwit has extensive experience in building high-performing sales teams across various sectors, including proprietary hardware, SaaS, and high-margin services. He is recognized as a multi-award-winning executive leader and has a strong background in both inbound and outbound sales strategies.