Meet The Team
Devin Bilello
CEO & Owner I HVAC Professional
With more than 15 years of experience in the heating and cooling industry, Devin Bilello brings hands-on HVAC expertise, leadership, and a strong commitment to serving local customers to DRB Services.
Devin began his career as an HVAC technician and worked his way into leading jobs, managing a team of six full-time employees, and taking on the many responsibilities that come with running an HVAC operation. His experience includes residential and commercial heating and cooling, refrigeration, boiler systems, service, and installation. He holds a refrigeration license and studied Heating & Cooling at Gateway Technical College.
Beyond his HVAC knowledge, Devin is a talented craftsman with a broad understanding of the many trades that go into building and improving a home. He has a particular talent for designing and installing HVAC systems, combining technical expertise with an eye for detail. He takes tremendous pride in his work, ensuring every installation is clean, precise, and thoughtfully executed. To Devin, a well-designed system is more than just functional; it should look as good as it works.
Before founding DRB Services, Devin spent 12 years working alongside his father, Ross Bilello, at Air Systems. Since 1990, Ross had built a respected HVAC business and a strong reputation throughout the local community for quality workmanship and dependable service. Devin learned firsthand from his father, gaining extensive experience in service while helping carry on the family's HVAC tradition. When Ross retired in 2024, he left behind a legacy of trusted service and craftsmanship that Devin is proud to continue.
In 2025, Devin took the next step in his career and founded DRB Services with his wife, Jackie, combining his in-field and business experience with their shared goal of building a local, family-owned heating and cooling company customers can trust. Today, Devin is putting that experience and family legacy into building his own business, DRB Services, and is doing an incredible job carrying that tradition forward while creating something of his own.
Oscar Delgado
Lead Technician I HVAC Professional
With more than 7 years of experience in the HVAC industry, Oscar Delgado brings a strong background in heating and cooling service, installation, troubleshooting, and repair to the DRB Services team.
Oscar is experienced in all aspects of HVAC work, from installations and routine maintenance to diagnosing and repairing heating and cooling systems. His hands-on knowledge and attention to detail make him a valuable part of the DRB team, whether he’s working on a new installation or helping a customer get their system back up and running.
After completing tech school, Oscar worked at Air Systems, where he continued to develop his skills and gain hands-on experience in the HVAC trade before joining DRB Services.
Beyond his technical expertise, Oscar is known for being friendly, dependable, and easy to work with. He takes pride in doing quality work while making sure customers feel comfortable and taken care of.
Jackie Bilello
Co-Owner I Business Operations & Marketing
With more than 10 years of professional experience in marketing, communications, graphic design, and business operations, Jackie Bilello brings a creative and organized approach to the day-to-day operations of DRB Services. Her responsibilities include office administration, bookkeeping, invoicing, payroll, customer communication, marketing, social media, website management.
Jackie co-founded DRB Services in 2025 with her husband, Devin. She brings more than seven years of marketing experience from the University of Wisconsin-Whitewater, where she advanced through multiple marketing roles before becoming a Marketing Assistant Director. During her time at the university bookstore, she led marketing efforts for a $3 million business, overseeing marketing strategy and execution while gaining extensive experience in management, team leadership, and cross-functional collaboration. She also worked with Air Systems as their marketing manager from 2021 - 2023.
Jackie holds a Bachelor of Arts in Graphic Design and Advertising and enjoys bringing her background in marketing and design together with the business and customer-service side of DRB.
Otis Bilello
Chief Happiness Officer
Otis is DRB Services’ resident shop dog and official morale manager.
He’s always ready to greet the team, supervise the office, and make sure there’s plenty of happiness around the shop. While he may not know much about HVAC, he’s an expert in being a good boy and he takes that job very seriously.
Why Choose DRB Services?
At DRB Services, heating and cooling is more than a business. It’s part of our family. The Bilello family has been in the HVAC industry for more than 40 years, and we’re proud to carry that tradition forward as a family-owned and operated heating and cooling company serving our local community.
Devin brings more than 14 years of hands-on HVAC experience and spent 12 years working alongside his dad, Ross Bilello, who built and operated a respected HVAC company for his entire career before retiring in 2024. Devin learned the trade, work ethic, and importance of taking care of customers from his dad and is proud to continue that family legacy through DRB Services.
Today, that tradition continues with our growing team. Oscar Delgado, our lead technician, brings 7 years of experience in the HVAC trade and shares our commitment to quality workmanship and taking care of customers.
Jackie brings a background in marketing, management, and business operations, helping lead the business behind the scenes and making sure every part of the customer experience reflects what DRB stands for. Together, we’ve built DRB Services around something we both value: working hard, helping people, and treating our customers like neighbors.
In August 2026, we welcomed our first baby, making this business even more personal to us. We’re excited to grow DRB Services, connect with more families in our community, and build something we can be proud of for years to come.
Whether you need heating repair, air conditioning service, HVAC maintenance, or help keeping your home comfortable year-round, we’re here to help.
DRB Services: Your Local Heating & Cooling Experts
Proudly serving Walworth County and surrounding Southeastern Wisconsin.
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