The Story of the Three Generations

Don’s family began roofing in Detroit, Michigan, in 1940 when Don’s grandfather, Henry “Hank” Oesterwind, opened the doors to Hank’s Roofing Company. Hank built a reputable company with his son Jim working along-side him. Jim (Don’s father) started his own company in Michigan but decided to move his growing family and business to Northern California in 1987 where he established Jim’s Roofing Company.

Don grew up roofing in the Bay Area in some capacity or the other. He started working on the job site with his father Jim when he was eight years old — a time when he was not allowed on the ladder or the roof. But that didn’t deter Don. He did the job site clean-up picking up the torn off roof, nails, and miscellaneous items that fall to the ground during roof installation. Today he describes this time of his life as “Golden. I was so happy I was working with my dad!” Don would purposefully find a way to get roofing tar on himself, so he would feel even more like a part of the roofing crew.

By 12 years old, Don was working with his dad and big brothers Jim Jr. and Dean after school, on weekends, and summers. By this time, he was allowed to work tearing off roofs and learning how to felt a roof. By age 13, he was laying shingles and absorbing all the knowledge he could from his father and brothers. Clients have always described Don’s father as honest and affectionately “obsessed” with installing an attractive roof that does not leak. Don admits he too is not happy if a job is not perfect.

At 16 years old, Don was installing entire roofs. Over the next two years, Don honed his technical and project management skills. When Dean, the foreman of the team at the time, decided to pursue a different path, Don became the foreman of his Dad’s company – pretty impressive given he had another older brother in the family business. Being a foreman requires the desire and skill to lead the team, direct the work, and effectively communicate with clients. Don held this position for 10 years. By then it was time to explore other roofing companies. Don joined Old Country Roofing (OCR) in 1999 as head of the warranty division (OCR is now a part of PetersenDean). OCR installed tile roofs on new construction projects all over California. At that time, one in three Bay area homes had a tile roof, so the knowledge and skill Don gained in repairing tile roofs is unmatched in the industry even today.

After several years working for OCR, the desire to run his own crew and business was calling loudly. Even though he liked working for OCR and they offered him a promotion into quality control it was time to follow his entrepreneurial spirit; time to follow in his beloved father’s footsteps. Roofing is what Don enjoys and is great at, so having his own roofing business was a natural transition.

In 2003 Don opened his business, Eastwind Roofing (a mash-up of the family name and the East San Francisco Bay service area), to serve the I-680 and Hwy 24 corridors. Further entrenching the his family as THE PROVIDER of quality roofing services for the entire East Bay and establishing the third generation of family roofing companies.

Don’s father has just recently retired, and Don has proudly welcomed and absorbed Jim’s clients, the northeastern Bay service area of Richmond, Pinole, and surrounding communities. Additionally, his brothers, Dean, John, and Mike who worked closely with their father until his retirement have now joined Eastwind Roofing.


Don’s brothers each bring expertise, a strong work ethic, and a commitment to quality to the company:

With over 30 years of experience, Dean (3rd on the left) brings multi-faceted knowledge of roofing systems. He’s a problem-solver which, coupled with his deep technical skills and natural abilities, make him a great foreman for Eastwind Roofing. Just as he was many years ago in his father’s business! Dean is known for quality workmanship and his clients really appreciate the skill he brings to every job.

John (right) is the hardest worker you will ever meet. He has a real compassion for people and in simply doing the right thing. He specializes in gutter repair and replacement and excels at customer service. He also brings 30 years of quality roofing experience to the company.

Younger brother Mike (second on the left) has been roofing for 10 years. The family describes Mike as a roofer from in the womb. He’s been in roofing in one way or another since he came into this world. He loves doing it, has excellent technical skills, and is dedicated to delivering a quality product for his customers.