Thomas “Tom” Randall Stiling, a cherished husband, father, and grandfather, passed away peacefully at the age of 70 on November 27, 2025, in Naples, Florida. Tom was surrounded by family at the time of his death, leaving behind a legacy of love, laughter, and adventure.
Born in Chicago, Illinois, on September 5, 1955, Tom was the son of the late Thomas O. and Mary K. Stiling. He spent much of his youth in Westford, Massachusetts, where he graduated from Westford Academy in 1973. Following high school, he earned a Bachelor of Science degree from Northeastern University in Boston.
Tom’s commitment to service was evident during his time in the United States Marine Corps. He enlisted in 1974 and served until his honorable discharge in 1979 as a sergeant specializing in manpower planning and special weapons. His military service included deployments to several key locations, such as Parris Island, Camp Pendleton in California, and overseas in Okinawa, Japan, Iwakuni, Japan, Osan, Korea, Subic Bay, and Mindoro in the Philippines, as well as ship duty on the USS Blue Ridge.
After leaving the Marine Corps, Tom transitioned into the burgeoning field of information technology. He began his career at Wang Laboratories as a Human Resources Director and later moved to Greensboro, North Carolina, in 1989. In 1991, he founded his first company, ORCA Technology, in Charlotte, North Carolina, which he ultimately sold to Seer Technology in Cary.
Tom’s entrepreneurial spirit led him to several successful ventures, including serving as Senior Vice President of Global Sales at Bluestone Software, which went public in 1999. He was the CEO of Curl Corporation, an MIT spin-off sold to Sumisho of Japan in 2004, and played pivotal roles in other startups, including SalesMethods LTD in London and Go2Group Inc, which was sold to Adaptavist in 2020. Tom also provided advisory services to CEOs through his company, Tidal Wave Partners, and held the position of Chairman of the Board at Goldfinger Holdings until his retirement in 2024.
In retirement, Tom dedicated his time to his family, particularly his children and grandchildren. He was known for his sports enthusiasm, participating in senior softball, tennis, and pickleball, while also being an avid fan of the New England Patriots, Boston Red Sox, and Boston Celtics. His warmth, kindness, and generosity made him a beloved figure among family and friends.
Tom is survived by his wife, Diana Stiling, and their children: daughters Nicole of Lowell, Massachusetts, and Val of Columbia, South Carolina, as well as son Tim of Cape Coral, Florida. He leaves behind grandchildren Addison, Max, Heidi, and an expected grandson, Henry. His siblings, Sherry, Dave, and Mike, along with their spouses, also survive him, as do many nieces, nephews, and friends. He was preceded in death by his former wife, Lorrie, in 2012.
A celebration of Tom’s life is planned in Massachusetts at a later date. The family requests that, in lieu of flowers, individuals reach out to old friends and embrace their loved ones, reflecting Tom’s belief in the importance of connection. Contributions in his memory can be made to any veteran organization or to his favorite charity, Toys for Tots.
As family and friends bid farewell to Tom, they find comfort in the enduring impact of his spirit, which will remain forever intertwined with the lives he touched. His legacy of love, joy, and adventure continues to resonate in the hearts of those who knew him best. Semper Fi—no one left behind.