2025 Ones To Watch - Rising Stars: William Cahillane, Pioneer CRE

“Will combines a deep expertise in real estate with a personable, collaborative demeanor. He brings regulatory insight and leadership to every project. His initial roles as a building inspector and municipal project manager led him to the private construction world, as well as being a licensed real estate agent. Will recently became the Building Commissioner for a Western MA town, and now spearheads Pioneer CRE’s construction advisory division, while also working as a commercial agent. Will’s diverse background, drive to learn, and ability to build strong relationships make him a standout.” - Paul Bongiorni, Owner of Pioneer CRE.

What recent professional milestone or project are you most proud of, and why? I am most proud of a recent retail tenant I represented. Their business has not only thrived in their new space, but it has also spawned a thriving community that surrounds the business. Commercial real estate professionals play a pivotal role in the communities we serve, and sometimes we are fortunate to play a role in building our communities up while bringing them closer together.

What’s one challenge you’ve overcome in your career so far, and what did it teach you? CRE is all about problem solving. A recent client was in the due diligence stage of acquiring a multi family structure that appeared to be riddled with local and state violations. Through meeting with officials and studying almost twenty years of documentation, I was able to put together a plan that lowered the risk profile for my client and brought the property back into compliance with the city. In the end, the structure became safer for the occupants and my client was able to realize a lower risk, value added opportunity. This taught me an important lesson about the due diligence process.

If you could give advice to someone just starting out in your field, what would it be? My advice would be to take one particular property that may be available for sale or lease, and to treat it as a case study. Every property has a different story, but by placing just one property under a microscope, one can observe a lot. I would suggest they look into the property’s current state, then assess the past, and then try to formulate a projection of where the property will be in ten years. Of course, this is important from a financial perspective; however, I would suggest they focus on the history of the property/area and review their projection 12 months to see what became true.

Who has played a pivotal role in your development, and how have they influenced you? Paul Bongiorni played a pivotal role in my development. CRE can sometimes feel like a big corn maze. It can be hard to get inside, and ever more difficult to know which way to turn once you’re in. Paul offered a refreshing perspective on CRE by being open for discussion and to ask questions, I think that’s the exact attitude to have. Paul has taught me that the best way to serve our clients in CRE is transparency, education, and collaboration. I try to take this perspective with me when communicating with clients, prospective newcomers to the industry, and anyone with questions in general.