Jon Krawczyk

Agent & Vice President

Jon Krawczyk is an experienced Employee Benefits Consultant based in Milwaukee, Wisconsin, advising employers across Southeast Wisconsin, Illinois, and multi-state organizations. He brings more than two decades of insurance and employee benefits expertise, helping small and mid-sized companies design, manage, and optimize benefits programs that balance cost control, compliance, and employee engagement.

Jon began his insurance career in 2002 after earning a Bachelor’s degree in Business Administration from UW–Oshkosh. He spent over 15 years with a leading global insurance firm, culminating in his broker role as a Senior Employee Benefits Consultant, where he guided employers on benefits strategy, plan design, and long term healthcare cost management. He later worked on the medical carrier side, gaining firsthand insight into underwriting, pricing, and risk evaluation, experience that strengthens his ability to advocate for clients during negotiations and renewals.

Since 2018, Jon has served as an Agent and Vice President at Robertson Ryan, partnering with business owners, CFOs, and HR leaders as a strategic advisor. His work extends beyond brokering coverage to include compliance guidance, employee education, carrier advocacy, and aligning benefits programs with broader business goals. Known for his direct, practical communication style, Jon helps employers navigate complex benefits decisions with clarity and confidence.

Outside of work, Jon enjoys spending time with his family and friends. His interests include travel, motorcycling, fishing, and Wisconsin sports.