R. Damon Ollerhead

R. Damon Ollerhead passed away peacefully on March 2, 2026, after a reoccurance of bladder cancer, he was predeceased by his spouse, Diane (Alioto) Ollerhead, who passed on March 15, 2025. They were married for 56 wonderful years. Damon was born October 28, 1939, in Brattleboro, Vermont. Damon spent his childhood in Gardner and Somerset, Ma. He graduated from Somerset High School in 1957, Northeastern University, (9 years evenings,) with a B.A. in 1977, and received his MBA from Babson College, (4 years evenings,) in 1981. This was all accomplished while working full time and bringing up a family with his wife.

His favorite number was 437,982. Damon had a mind for business from the beginning. One of his first jobs was picking strawberries at 7 years old. Damon wasn't making enough money, so he began to put the green strawberries on the bottom of the basket and the ripe berries on top. He was fired. Too ambitious! He looked at all of this as a business opportunity. He had many corporations of his own. He came up the hard way, beginning his career in 1958 at Raytheon Co. in North Dighton, Ma. His career culminated as a turn-around business consultant for NASA and DOD, establishing profitability to many corporations. Damon's management philosophy was simple: give accountability, praise and development advice. He believed that his only job was to provide the necessary resources to those on the front line so they may be successful, as they knew their job better than any manager.

Damon and Diane moved to Cape Cod in 2003 from Needham, MA. The town of Barnstable hired him during his retirement years as a greeter, and ambassador, for the town. He was assigned to the JFK Memorial. Damon sold JFK memorial hats and collected donations for the memorial scholarship fund and youth sailing programs for the last 22 years. Damon's winter position was at the Hyannis Youth and Community Center as a supervisor. He found his passion for writing, later in life. His goal was to become a successful author, which he accomplished. He published two fiction novels, with a pen name of Rolfe Damon.

He was very politically minded; always watching Newsmax and Fox News. Damon was a staunch republican.

Damon leaves behind his daughters Kimberly, and her husband Edward, Courtney and her husband Christopher. He was so proud of his girl's successes! He leaves them with a few final words: "Continue to be creative and unique. Do not be a follower but a leader! oxoxo." He also leaves behind his beloved grandchildren Blake and Brent. Ya-Ba-Doozie guys, love you forever!

He is survived by his brother, Doug and his wife, Gail. Niece, Kristen, and nephew, Jason, and their families. In addition, his brother-in-law, Paul Alioto, his wife sis, and his nieces Allison and Brittany. Also, survived by his brother-in-law, Joseph Alioto.

Damon and Diane are now reunited, "with everlasting love!"

In lieu of flowers, donations can be made to St Jude Children's Hospital in Memphis, TN. in Blake Schroeder's name.

Visitation will be on Tuesday, March 10, 2026, from 4-7 PM at Chapman Funeral & Cremations, John -Lawrence Chapel, 3778 Falmouth Road, Marstons Mills. The Funeral Service will be on Wednesday at 11 AM in the funeral home. Burial will follow at Oak Neck Cemetery.