Meet The Team

Michael has been in roofing and construction since 1972. He was formally trained as a cabinet maker and a finish carpenter at Blue Hills Regional Technical School. He is certified as a CertainTeed SELECT ShingleMaster, Master Shingle Applicator, GAF Master Elite Roofing Contractor, and Owens Corning Platinum Preferred Contractor.

Michael created O’LYN Roofing in 1974, and from the very beginning, his reputation for quality work was and remains the company’s most valuable asset. O’LYN Roofing quickly earned the nickname “The Victorian Specialist” because of his attention to detail, old-world carpentry skills, and knowledge of and expertise with traditional and historic roofing materials and techniques. His most famous quote is, “I love a challenge. The more challenging a project is, the more I enjoy my work.”

Michael particularly enjoys selling, working with managers, and attending conferences to improve the company and the roofing industry.

When he’s not hard at work, Michael loves to spend time with his family, especially his grandkids. He also loves boating, lobstering and traveling, especially when he can do it with family and friends.

Linda helped her husband, Michael Olen, start O’LYN Roofing in 1974. As the President she enjoys growing the company and providing employment opportunities.

In her spare time, Linda loves spending time with her grandchildren and boating.

Todd has been in the service industry for over 30 years and a manager in construction and home improvement since 2006. He holds a Construction Supervisor’s License (CSL) and is OSHA and lead safety certified. Todd served as O’LYN’s Production Manager from 2011 through 2017. In January 2018, He was promoted to General Manager. His daily routine involves overseeing all day to day operations of the company. What Todd likes most about his job is the challenge to be a great coach and strong leader of the great team of employees at O’LYN.

When he’s not working, Todd enjoys spending time with his family, playing golf, cooking outdoors, and working on DIY projects of his own.

As the Production Manager, Jacqie has held previous roles at O’LYN, including production assistant and was a member of the customer service team. Prior to joining O’LYN, she was a paralegal.

She loves working here because of the positive atmosphere and the core values. She is organized, detail-oriented and a team player.

In Jacqie’s spare time, she likes to hike and spend time with her family.

Dennis has over 30 years of accounting experience and is a former QuickBooks Professional Advisor. He specializes in streamlining accounting policies and procedures. Over the years his experience spans across several industries from contemporary high-end retail to the oil industry.

Dennis’ attraction to O’LYN, as he states, was that the job description was a perfect match and his desire to be a part of a team that is committed to working together and moving in the same direction. His attention to detail and organizational skills assists us to make informed decisions and his experience in efficiencies are truly an asset to the O’LYN Team.

You will find Dennis in his spare time walking on a beach or in the gym many times throughout the week. He is also fond of hanging out with his family and loves to eat. Although Dennis resides in Weymouth now, he once lived in a refugee camp for one year on a remote island in the Philippines teaching English to Vietnamese refugees. He also played in the Philippine Professional Basketball league and won MVP.

Tucker loves watching the construction process, particularly seeing a home transformed by a new roof with architectural style. He also enjoys finding new ways to engage with homeowners and the opportunities new technology can bring.

Outside of work, Tucker enjoys skiing, hiking, working out, and chilling with the family husky. Anytime there’s a beautiful day he’s tempted to take a joy ride with the windows and sunroof open.

Shawn’s background provides the right mix of experience, skills, and empathy. As a former aviation mechanic, he knows firsthand how very important it is to get it right the first time. In aviation, there are no second chances. “Doing the right thing and getting it right the first time really isn’t that difficult.” Not with the right experience and integrity. “I’m just not happy until I have a definitive solution to the problem.”

Having obtained the highest certifications from Owens Corning, CertainTeed, and Air Vent, Shawn will provide a thoughtful and lasting solution to every problem.

Shawn’s day-to-day outlook is to provide homeowners with peace of mind. Peace of mind comes from working together toward what is best for the house and owner. “I’m lucky. I get to meet a lot of interesting people and help them.”

After hours, Shawn can usually be found at home with his daughter, Peyton, and two dogs, Abby and Greta. If time allows, he might be in the garage working on his old BMW.

Bob’s background started in Hospitality Management, managing high-volume restaurants in the Boston area for a national restaurant chain. He spent 23 years as a Sales Manager with manufacturers in the consumer food and packaging industry.

Starting in the Home Improvement industry in 2005, managing Wholesale Club Sales for a Boston Home Improvement Company, he then transitioned to O’LYN Roofing in 2011 and enjoys the consultative approach and value that O’LYN Roofing brings to the industry.

He realized that building envelope science was a fascinating field, so much more goes into a roofing system than just the shingles, so he earned the highest certifications with the industry’s top manufacturers and believes that a “total roofing system” is imperative with the ever-changing building and energy codes.

Bob has two sons and a fiancé and, enjoys sports, the outdoors, music, and is a hacker on the golf course.

Jim was introduced to the roofing business when he was 20 years old and then served as a foreman in the roofing union for 25 years. His passion for the roofing industry is undeniable and working at O’LYN is truly a match.

Jim enjoys working for O’LYN for many reasons. He says he likes the fact that the company treats their customers and employees professionally and, most of all, the charitable donations to several important causes.

When Jim is at home, he’s still learning new ways of tackling projects around the house. In his downtime, he enjoys playing and coaching sports with his kids. In the summer, you’ll find him relaxing on the beach or grilling.

Joe is a United States Army Veteran and has over 45 years of professional home improvement experience. He likes that O’LYN is a family-owned business and has been around for 50 years with great products, high Google customer ratings, in-house service plus value pricing. Joe is also a proud father of 4 children and a grandfather of 13 kids. When he is not at work, he is a drummer in two bands (one of which is famous).

John advanced from our Customer Service team to become a member of our Roof System Specialists. He has a background in enterprise technology sales and absorbs knowledge and adapts fast. He is quickly becoming an expert in the roofing field. “I’m fortunate to be with a company that is proud of its reputation and quality of work. I have so many colleagues with a wealth of knowledge in the industry. There is no better place to learn than O’LYN Roofing,” said John.

When asked what he likes about working at O’LYN, John states that “the familiarity and closeness of the entire company is incredible, which leads to a caring team that is always happy to help each other.”

John is passionate about organic farming, cooking, and baking. He enjoys watching sports and practicing jiu jitsu in his spare time. When he is relaxing, John loves yoga and meditation. You will find John often volunteering at local organizations and community events.

Born and raised in historic Quincy, Massachusetts — the “City of Presidents” — Bill now lives in Whitman, famously known as the birthplace of the Nestlé Toll House cookie. With a background in home improvement sales specializing in windows and flooring, Bill brings a strong foundation of industry knowledge and a customer-first mindset to the O’LYN team.

Integrity and honesty are the cornerstones of Bill’s approach, making him a trusted asset both to the team and the homeowners he serves. Drawn to O’LYN because of its family-owned values and genuine care for the customer experience, he takes pride in being part of a company that puts people first.

Looking ahead, he is excited about the opportunity to continue helping people while providing for his own family — a balance that fuels his drive and dedication every day.

Outside of work, you’ll likely find him in the garden or enjoying time with his family. His favorite role in life? Being a husband and a father — nothing compares.

Guy started works as a service technician for O’LYN in 2018, but he has over 23 years of roofing experience under him. Today he is working for O’LYN doing various types of jobs including slate roofing, cedar shake roofing, metal roofing, and flat roofing.

During his free time, Guy enjoys raising chickens, goats, ducks and turkeys on his small farm.

Dan is the ideal Roofing Supervisor. He has been in the trade since 1992 and his experience spans across the entire home improvement industry. Over the years he has maintained his professionalism and is often noted for his courtesy by homeowners.

What Dan likes most about working for O’LYN is the security of a well-established company that will be around for the long term.

You might notice Dan in several O’LYN TV commercials as he has appeared in several over a 10-year span. In his spare time, he enjoys keeping in shape by body building and power lifting.

John has been a carpenter since 1976, framing roofs, installing siding, and doing finish and trim work, and running his own business doing it for 26 years.

He has been with O’LYN since 2011 and specializes in wood work involved in roof projects along with general roof repair. This includes things such as Victorian gingerbread details, wood gutters, as well as composite (Azek) wood replacement. He particularly enjoys the challenges that each different job presents.

When he’s not working, John enjoys camping and skiing with family and friends most of all.

Richard has previous experience working as a solar panel technician. He enjoys O’LYN’s work environment and great co-workers. In his spare time, Richard likes to spend time with his family and watch sports.

Steven has over 13 years of experience working with shingle and rubber roof systems. He enjoys working with a team who is very professional and respectful. In his spare time, Steven likes to spend time with his family and play basketball.

Scott is a veteran of the United States Marine Corps. His extreme attention to detail and extensive critical thinking in an active steady environment is an asset he brings to the O’LYN team. Now that Scott has recently returned to his hometown of five generations, he is looking forward to enjoying more time on woodworking and carpentry projects.

Scott brings his contagious laughter and his sense of humor to the O’LYN team. In fact, his laughter will make you laugh harder! When he thinks about working at O’LYN, Scott likes the “friendly and comfortable atmosphere coupled with the abundance of help from the crew.”

When he is not at work, Scott looks forward to taking day trips with his family, spending time with his vast array of animals, fishing, and golfing.

Daren brings his professional experience of recruiting, hiring, and training employees as well as managing people and processes to O’LYN Roofing. He credits his ability to guide individuals toward their goals and foster collaboration because of his former teaching experience.

He genuinely enjoys helping candidates find the right opportunity and supporting team members in their growth. Daren says he was drawn to work for O’LYN because of the company’s commitment to excellence and values teamwork and trust.

Daren likes the outdoors. His favorite ways to unwind are fishing, hiking, hunting, and a great round of golf. To recharge, he loves having fun with his family! On the weekends you can find this former music teacher playing his bass at local gigs with his bandmates.

Stacey has experience working with customers to provide a positive experience. She also works as a server and bartender. Stacey enjoys working at O’LYN not only with her co-workers but feels O’LYN makes a true effort to go above and beyond with knowledge, product, professionalism, and customer service.

In her spare time, Stacey likes to spend it with her family.

Owain has over 7 years of customer service experience and is dedicated to assisting others. He enjoys working daily with such a tight-knit group and feels O’LYN is a place where hard work is truly valued.

You can catch Owain when he isn’t working, watching the Celtics game, or playing his favorite video games.

Originally from Boston, MA—home of the infamous Great Molasses Flood—Destiny Brooks now lives in Quincy, bringing with her years of experience in customer service and call centers. With a natural ability to connect with people and a warm, upbeat personality, Destiny is a standout member of the O’LYN Roofing team.

Her passion for helping others and her exceptional attitude make her a key asset in creating a positive experience for every homeowner who contacts O’LYN. Destiny was drawn to the company’s strong reputation and supportive culture—and appreciated that during the hiring process, the Recruiting Coordinator recognized her strong communication skills and natural customer-first mindset—qualities that continue to shine in her role today.

Looking ahead, Destiny values the tight-knit, collaborative atmosphere at O’LYN’s call center, where every team member plays a crucial role and there’s always room for a few good laughs along the way.

Outside of work, you’ll find Destiny enjoying nature, hiking, beach days, and quality time with her family. She’s also a creative spirit—crocheting, making candles and soaps, and embracing all things DIY.