CBIZ Gibraltar Insights And Resources

Do You Know Bill Main? Get to Know Gibraltar

Bill Main has been an integral part of the CBIZ Gibraltar team since the company’s inception in 1998. His focus is on exclusively representing clients across all aspects of tenant advisory services, including strategic planning, lease restructuring, lease negotiation, site selection, acquisitions, benchmarking, and facility disposition.  

As part of our Get to Know Gibraltar series, we sat down with Bill and asked him these questions:

What part of your working day makes you think “This is why I do this job?”

The people! I love having the opportunity to work with so many talented people every day, including our team, clients, leasing agents, attorneys, architects, owners, etc. It’s always interesting working with multiple parties with different viewpoints about how a project should move forward. Helping clients work through challenging complex issues, and finding the best solutions is extremely rewarding. It’s about knowing our clients are satisfied with the outcome — that is what continues to drive and push me to do the best on every project for every client.

The other benefit or rewarding element of my job that we get to work closely with so many different types of organizations, from big to small and across industries. I love seeing news about the success our clients achieve, and it’s a privilege to have helped them with their workplace where great work is coming to life.

What are the most memorable client projects you worked on to date? Why?

There are so many memorable projects, and the more challenging the better! It is impossible to identify the “most” memorable. That said, a few that are top of mind include, the Chicago Title HQ Project, the Elevance HQ requirement, the CBIZ KC projects and the Ariel Investments renewal renegotiation. Needless to say, there are countless others.

How do you want people to feel when they first walk into the office? How should they feel 10 years from now?

When an employee enters a workplace, I want them to feel like they are at home, and that the office fits their culture and embodies who they are and what they do. That is really what we always strive for in our work; the right environment for your business.

After a decade in a space, I want tenants to think, “Wow! The last 10 years flew by.” It seems that time flies when you are in a comfortable setting and things are moving along in a productive environment that is designed to suit the needs of your company, business objectives, and employees.

Alternatively, I want them to be in a very different expanded space due to their business success!

Why do you prefer to work in the physical office environment?

That’s easy, the people. It is all about being around peers and colleagues. When you are around your team, it just creates a much better dynamic that really motivates me.

What advice would you give young real estate professionals and workplace experts?

First, try to find a great team and strong mentors — these are really important in any career.

Next, remember that we are not working in a simple industry or easy career field where results happen overnight. You need to put the work in. If you work hard, apply yourself and are patient, the reward is really special.

Finally, always, always think about the best interest of the clients and other people, and handle yourself with integrity. If you focus and always think with your client’s best interests in mind, it will pay dividends for everyone.

What are some of your favorite buildings or offices spaces in Chicago?

There are hundreds of them for me. If I had to name a few, I’d start with two of the most iconic buildings: Willis Tower and Aon Center. As a kid growing up in Chicago, I remember driving with my dad into the city for a Bears game and being in awe as we approached downtown and saw these buildings.

River Point at 444 W Lake also comes to mind. I have a client in that building and think they did a great job with that property.

Last, 303 W Madison, 1 S Wacker, and 225 W Wacker are also on my list. I have had an amazing experience and great memories working in offices in all three amazing buildings.

What do you like to do when you’re not at work?

Spending time with my family and friends. In our house free time is completely occupied by with baseball and basketball for our two boys, any additional time we try to sneak up to Lake Geneva, which we love! All that said, I am never not at work, and always available.


Bill is a devoted advisor to his clients, which includes a diverse collection of major corporations, entrepreneurial firms, professional service firms, tech, non-profit organizations, higher education, and healthcare. He has a reputation for completing complex real estate transactions for organizations in many markets and including unique property types. He has completed projects with landlords extending throughout the United States, and has completed in excess of 1,000 transactions over his career, in almost every major and 2nd tier market.

CBIZ Gibraltar is comprised of professionals from a variety of backgrounds, spanning a broad range of real estate expertise and experience. We share in a common focus of accountability, integrity and responsiveness.