Meet the Team

How do we describe our Chief Operating Officer, Bryan Sipple? Let’s just say he was born to be a builder! As a 4th generation carpenter, there was never a doubt that he would go on to a successful career in the construction industry. While working with his grandfather and father since age 12, they instilled in him the discipline and drive that he possesses today. Bryan credits his mother for his outgoing personality and charisma.

Bryan’s strong work ethic and commitment to quality is what built Classic Custom Homes. He is not just building the American Dream, he’s living it! Working side by side with his wife Jennie, they have proven that with discipline and hard work, anything is possible.

Bryan has been in the construction field for over four decades. His expertise is in new home construction, multi-family construction, and residential and commercial remodeling. He has worked hands-on in many aspects of construction, and now project manages each and every project himself. This personal hands-on approach and attention to detail is just another thing that separates CCH from the others. With the reputation of Classic Custom Homes on the line, it is important to Bryan that the finest quality products are used and delivered for an affordable price.

Giving back to others in need is very important to Bryan and Classic Custom Homes. Bryan gives generously to the American Cancer Society after losing some dear friends and family members to cancer. He also gives to the Shiners Hospital for Children. Classic Custom Homes also teamed up with Habitat for Humanity for a Frame Up event.

When Bryan is not working, he enjoys spending time at his cabin. A true outdoorsman, his best days are spent with friends and family while snowmobiling, 4-wheeling, or boating.

Jennie has worn many hats over the years at Classic Custom Homes. She has been involved in nearly all aspects of the business and has served in virtually every capacity of the organization. She is currently acting as VP, Controller and Rental Specialist. As a licensed Realtor, she negotiates the best possible land costs for each project.

Jennie’s work experience has been in construction since 2005 when she joined her husband Bryan in Classic Custom Homes. Prior to joining the company, Jennie was a Lean Six Sigma Black Belt focusing on quality and process improvement by identifying inefficiencies and waste. Prior to her Quality Management career, she spent 19 years in the travel industry as a Travel Agent, Travel Agency Manager and Owner, and finally a Corporate Travel Call Center Manager.

Jennie attended the University of Wisconsin-Eau Claire studying Psychology and Marketing. She obtained a degree from Travel Careers School in Milwaukee, WI and later her Lean Six Sigma Black Belt Certification from Six Sigma Academy.

Once again, the American Cancer Society is the charity of choice for Jennie and the Sipple family. She also gives generously to the American Family UW Children’s Hospital, St. Jude’s Children’s Research Hospital, and the Alzheimer’s & Dementia Alliance of Wisconsin. These facilities do life-changing work each day, and Jennie gains much inspiration from their actions. She has also donated time and energy to Habitat for Humanity and Extreme Makeover Home Edition, although I don’t know how much “talent” she brought to the building process!

When Jennie is not working, she enjoys spending time at her cabin with Bryan and friends & family. She enjoys traveling, snowmobiling, 4-wheeling, golfing, and hanging out with her daughter, Bailee. Jennie likes to relax with her dog Poppy, our office greeter.

Brea has led the Interior Design team here at CCH since 2015.  She assists customers with choosing both interior and exterior selections from start to finish – all the way from doors, windows, siding and roofing to paint colors, window coverings, and cabinet hardware.  As an in-house interior designer, she will help to keep you on schedule, on budget, and on top of new trends and products!  She is also responsible for ordering material and cabinet drawings for current clients.

Homegrown here in the Madison area, she worked as an interior designer for a small local business in Central Wisconsin, assisting customers with furniture selections and began her lifelong passion for cabinetry.

Brea enjoys time with her husband, son, daughter, and family, and two precious babies (of the feline variety).  She also enjoys yoga and kayaking.

We love that she has such a big heart – she volunteers at local charity events (AJN Freedom Isn’t Free and the Cow Chip Festival).  She also has volunteered at the food shelter.

Darin started with Classic Custom Homes back in December of 2014.  He is one of our carpenters and works directly with both the construction managers and subcontractors on the project.

Darin has been in the building trades since he was 18.  He was always interested in woodworking and advancing his knowledge in the building trades.

When not working, Darin loves to get out and run/bike triathlons and duathlons.  He lives in Sun Prairie with his wife Michele and two girls, Eve and Ella.

Dave works as part of the ‘Painting Division’ here at Classic Custom Homes.  They work on interior trim painting, exterior painting, and custom wall/ceiling painting for the new construction homes, remodels, and commercial projects.  They also handle the warranty, service calls, and touchups required before and after homeowner’s move in.

A graduate of the University of Wisconsin – Steven’s Point, Dave holds a Bachelor’s of Science degree.

He has been married for over 25 years and has four children, ages 15-22.  He currently lives in Reedsburg.  After college, Dave worked for the State of Wisconsin for nearly twenty years and returned to painting with his father-in-law before he retired from his business of over forty years (whom he worked for during the summers in high school).

Dave likes to bow hunt, make walking sticks, and referee hockey games in the winter.

He makes frequent donations to the Sacred Heart Catholic Church.

Sherry is a member of the Interior Design team, and Service Coordinator. Her journey with Classic Custom Homes began as a client, and her passion for design ultimately led her to become a part of the staff. She is committed to supporting you through every step of the selection process, as well as addressing any warranty or service needs that arise after your home is completed.

Prior to her joining our team, Sherry attended Northern Illinois University where she studied Analytical Chemistry. After conducting research and development in the pharmaceutical industry for 30 years she decided to pursue her passion for interior design and started her own business in 2015. Sherry’s dedication to our clients makes her a valuable asset to the Classic Custom Homes team.

Outside of work, she enjoys spending time with her husband and their combined six children and ten grandchildren. She loves cooking, exploring new places, swimming, and spending time outdoors. Sherry and her husband live on a beautiful 40-acre wooded property in Fall River, with their beloved hunting dog, Jackson, who ironically is afraid of guns.

Sherry also generously gives to St. Jude Children’s Hospital and the Alzheimer’s Association.

At Classic Custom Homes, Jenn takes on multiple roles, including serving as a Designer within the Interior Design team and overseeing Marketing efforts. She is responsible for creating design components, such as cabinetry drawings, tile design drawings, amongst other key design elements.

With over 10 years of experience in kitchen and bath design, Jenn brings a wealth of knowledge and expertise to the team. She graduated in 2013 with an Associate Degree in Interior Design from Madison College and is currently pursuing her degree in Architectural Technology.

Outside of work, Jenn lives in the Milton area and enjoys spending time with her significant other and children. On weekends she can be found cheering on her son during hockey games or her daughter at softball games. Jenn is also actively involved with the local 4-H Chapter as a board member, and project leader for dairy goats and horticulture. She can often be found in the garden, working on craft projects, or spending time in the barn with their animals.

As the Accounting professional at Classic Custom Homes Jalika is responsible for ensuring that all financial aspects of the business are accurately managed, and her wealth of knowledge and expertise in the field make her a valuable asset to the team.

Jalika graduated from Texas A&M University in 2020 with a degree in Accounting. Soon after graduating she made the move to Wisconsin and then joined the Classic Custom Homes team. She is deeply passionate about accounting and is always looking to expand her knowledge in the field.

When she’s not working, Jalika loves spending time surrounded by nature. Whether it’s taking long walks, going on hikes, biking, or just exploring the great outdoors. With her dedication to the industry and her love for the outdoors, Jalika is an important member of the Classic Custom Homes team.

Ron is the Lead Draftsman at Classic Custom Homes he is responsible for overseeing the accurate and efficient production of all drawings. With 20 years of experience in the architectural industry he is a true asset to the team at Classic Custom Homes.

Ron was born and raised in the St. Croix River Valley in Wisconsin. After earning his degree in Architectural Design, he made the move to Texas, where he honed his drafting skills. Recently, Ron decided to make the move back to Wisconsin to be closer to his family.

Outside of work Ron enjoys spending time in the great outdoors. He loves camping, and fishing.

As the Construction Operations Coordinator at Classic Custom Homes, Kristi handles a wide range of responsibilities from scheduling jobs to bidding on current and prospective projects.

Kristi is a seasoned project coordinator with 20 years of experience in the construction industry. The last 10 years she has focused on residential single-family homes, where she has honed her skills as a project manager. We are pleased to have her attention to detail, and construction knowledge on our Classic Custom Homes team.

Born and raised in Seattle, Washington, Kristi made the move to the Spring Green area over 15 years ago. Today, she lives on a farm with her husband, son, daughter, and a menagerie of animals, including 7 dogs, horses, and cows. Off the farm Kristi enjoys spending time with her family, and watching her children play sports.

Poppy is the office greeter!

When she isn’t greeting you at the door, she can be found basking in a sunny spot or curled up in front of her very own heater!