Our Legacy

A Foundation Since 1885

Heil & Heil was established over 140 years ago as a cornerstone of the Illinois business community. While the world of insurance has changed since our founding, our presence in the North Shore has remained a constant, a permanent home for the risks and legacies of the families we serve.

1972: The Modern Era Begins

The modern history of our agency began in 1972 under the leadership of Jim Flanagan. Jim was a visionary who understood that the strength of an independent agency lies in its ability to merge local knowledge with specialized service. He spent decades building the culture of integrity and technical focus that still defines us today.

2007: Preserving the Culture

Following Jim’s unexpected passing, the future of the agency rested on a pivotal choice: to be absorbed into a large corporate entity or to fight for its independence. Bob Landers, Jim’s long-time right-hand man and CFO, chose the latter. He purchased the firm from the estate specifically to protect the "people-first" culture Jim had built, ensuring that our clients would never be treated as mere account numbers.

2008: A New Generation

In 2008, Jessica Jankowiak officially joined the firm, beginning her career by learning every facet of the business from the ground up. Over nearly two decades of mentorship and growth, she helped refine the agency’s focus toward specialized advocacy for complex industries.

2025: Continuing the Stewardship

In 2025, Jessica purchased the agency from her father, marking a new chapter of family leadership. Today, as Principal, she continues the work Jim and Bob started, preserving the firm's independence and ensuring that Heil & Heil remains a boutique sanctuary of specialized knowledge in an increasingly consolidated industry.