With over five decades in the insurance industry, John R. Smalley brings unmatched expertise in surplus lines and wholesale insurance brokerage. His career began in 1969 and has included leadership roles at firms such as Swett & Crawford, Aris Insurance Services, and Tradewinds Insurance Brokerage. Currently a Wholesale Broker at R.E. Chaix & Associates, John has successfully built and managed offices, handled underwriting for large MGA programs, and worked with hundreds of agents and carriers across the U.S. His hands-on experience in program development, property, general liability, environmental, trucking, and professional lines sets him apart as a trusted industry veteran.

John’s approach is rooted in accountability, strategic growth, and long-term relationships. Whether he’s underwriting complex risks or leading teams, he focuses on creating value through consistent performance, clear communication, and strong carrier partnerships. Over the years, he’s built a reputation for integrity, reliability, and an unwavering commitment to getting the job done right. His passion for mentoring and developing operations has played a key role in the growth of multiple firms throughout his career.

Outside the office, John enjoys spending quality time with family and reflecting on a career full of stories from the ever-evolving world of insurance. With a deep appreciation for history and industry evolution, he brings a sense of humor and perspective that colleagues admire. His legacy includes not just decades of insurance excellence, but also the mentorship and professional development of countless peers in the field.