Real Estate Portfolio Advocacy

Heil & Heil: A Consistent Foundation in Real Estate Since 1885

At Heil & Heil, our legacy is rooted in the technical complexities of real estate insurance. Having originated within the property management industry, our agency possesses an "operator’s perspective" on risk—an advantage that allows us to look beyond the policy and into the daily functional realities of the buildings we protect.

We provide specialized technical advocacy for a wide range of property portfolios, with deep-seated experience in:

  • Common Interest Communities: Condominium Associations, Homeowner Associations (HOA), and Townhome Associations.

  • Multi-Family Residential: Apartment Complexes and high-density housing developments.

  • Commercial & Industrial: Dedicated Commercial Buildings and Mixed-Use properties with varied tenant exposures.

Our approach combines decades of hands-on property experience with the technical precision required to safeguard your most significant assets. We ensure that your investments are protected by a team that understands the nuances of property law, building systems, and investment risk from the ground up.

Below are our specialists who lead these efforts, supported by an agency-wide commitment to the craft of real estate insurance.

Nels Benson

Commercial Specialist

847-733-2675

nbenson@heilandheil.com

Nels began his insurance career in 1986 and has been a cornerstone of Heil & Heil since 1995. His professional focus is centered on the real estate and construction industries, specifically serving investors, property managers, developers, and contractors. Nels recognized early on that these sectors were often underserved, and he has dedicated his career to providing the comprehensive, clear protection they require.

Acting as a long-term partner rather than a broker, Nels prioritizes advocacy and clarity. He monitors emerging trends and coverage shifts to ensure his clients are prepared for industry changes before they happen. As part of a 140-year independent legacy, he takes pride in the agency’s reputation for reliability and its commitment to being a constant resource for the Chicago area.

The multi-generational nature of Heil & Heil is a point of professional pride for Nels, as he works alongside family within the agency. This family-centered approach extends to his clients, many of whom have relied on his guidance for decades.

Outside of the office, Nels has been married for 37 years to his wife, Sonia. He is a proud father and grandfather who finds his greatest inspiration in the outdoors. Whether spending time with his grandkids, AJ and Addie, or his black lab puppy, Muddy, Nels remains deeply rooted in the community he serves.

Alex Romano AAI, CRIS

Vice President of Sales

847-733-2620

aromano@heilandheil.com

Alex focuses on providing risk management and insurance advocacy for the construction and real estate industries. His perspective is deeply informed by his roots; having grown up in the industry and worked in the field prior to his insurance career, he understands the unique operational and safety challenges that contractors and developers face every day.

Alex prioritizes long-term stewardship over individual transactions. He holds both the Construction Risk and Insurance Specialist (CRIS) and Accredited Adviser in Insurance (AAI) designations—credentials that reflect his commitment to providing a technical foundation for his clients and partners. He approaches every relationship as a partner in the boardroom who still understands the reality of the job site.

As part of a 140-year independent agency, Alex values the firm’s reputation for reliability and its commitment to being a constant resource for the Chicago area. He ensures his clients have a direct, responsive advocate in their corner who is focused on protecting their growth and their workforce for the long run.

A resident of Wilmette, Alex is deeply rooted in the local community. Outside of the office, he is a dedicated family man who enjoys exercising, following sports, and spending time with his wife, Brittany, their two children, AJ and Addie, and their dog, Riggins.

Jack Benson, ACLC

Commercial Specialist

847-733-2694

jbenson@heilandheil.com

Jack provides specialized risk management and insurance advocacy for real estate investors, food manufacturers, and the hospitality industry. His focus on these sectors grew from a personal interest in the stories behind Chicago’s buildings and a deep respect for the craft of the city’s chefs and restaurateurs.

As an Accredited Commercial Lines Consultant (ACLC), Jack views insurance as a tool to help a business grow rather than a hurdle to overcome. He prioritizes speed, detail, and clear communication, ensuring that insurance requirements never slow down a client’s momentum. By learning the unique history and future goals of every operation he serves, Jack provides a level of stewardship that is tailored to the individual journey of the business owner.

Being part of a 140-year independent legacy allows Jack to provide the personal, responsive service that busy business owners require. He believes that the most valuable service an advocate can provide is "lightening the load" for his clients, allowing them to stay focused on their own growth and success.

Outside of the office, Jack is an avid supporter of the Chicago White Sox and enjoys exploring the city’s evolving restaurant scene. He values time spent with his family—especially his niece and nephew—and stays active during the winter months skiing.

Michael Levin

Commercial Specialist

847-733-2681

mlevin@heilandheil.com

Michael focuses on providing risk management and insurance advocacy for real estate investors, manufacturers, and contractors. His professional interest in how businesses scale led him to obtain his real estate license early in his career, providing him with a foundational understanding of property and investment exposure.

Michael approaches every client relationship as a partnership. By conducting site visits and focusing on the day-to-day reality of an operation, he helps identify risks before they impact a client’s growth. As part of a 140-year independent legacy, he combines the market reach of a large firm with the accessibility and personal attention of a family office.

Outside of the office, Michael is an avid golfer and racket sports enthusiast, playing both padel and pickleball. He and his wife, Lina, enjoy exploring the outdoors with a goal of visiting two national parks each year, accompanied at home by their French bulldog, Lucci, and their cat, Jaymo.