Thomas Randall Stiling's Obituary
Thomas “Tom” Randall Stiling, 70, a beloved husband, father, grandfather, family patriarch and friend, passed away peacefully at 4:16pm in Naples, FL on November 27th, 2025 surrounded by the love of his family.
Born in Chicago, IL on September 5th, 1955, he was the son of late Thomas O. and Mary K. Stiling. Tom grew up primarily in Westford, MA, graduated from Westford Academy in 1973 and received his Bachelor of Science degree from Northeastern University in Boston. Tom was a veteran of the United States Marine Corps, serving proudly from 1974 and honorably discharged in 1979 as a sergeant in manpower planning and special weapons expert with deployments to Parris Island, Camp Pendleton CA, 1stMAW Okinawa Japan, Iwakuni Japan, Osan Korea, Subic Bay & Mindoro Philippines, ship duty on the USS Blue Ridge, and finally MCRD San Diego.
After discharge from the USMC, Tom joined the early transformative days of information technology with Wang Laboratories as a Human Resources Director. Tom was soon relocated by Wang to Greensboro, North Carolina in 1989. After leaving Wang in 1991, Tom started his first company ORCA Technology in Charlotte, NC and eventually sold his company to Seer Technology in Cary, NC. After ORCA, Tom started on a series of successful startups including Bluestone Software (IPO’d in 1999) as SVP Global Sales, Curl Corporation as CEO (MIT spin-up sold to Sumisho of Japan in 2004), SalesMethods LTD of London, and Go2Group Inc as CEO (sold to Adaptavist of England in 2020). He also was a CEO Advisor with Gartner. Tom then formed his own software CEO Advisory company Tidal Wave Partners which led to the founding of Goldfinger Holdings as Chairman of the Board, eventually retiring in 2024 after his final M&A transaction selling ConnectALL LLC to Broadcom Inc.
While devoting his retirement stage to his children and grandchildren, Tom was always a sports fanatic - with his passion for playing sports to include senior softball, tennis, pickleball, and trivia along with watching his beloved Patriots, Red Sox, and Celtics. Tom was a kind, caring, fun-loving person who deeply loved his family and friends. He was a gracious and generous host to all, and was known for his laughter and warm, welcoming heart. Above all, Tom adored his wife, children, and grandchildren, who were the light of his life. He took great pride in his role as “Big Papi.”
Tom is survived by his cherished wife Diana in Estero, Florida; daughters Nicole (Lowell, MA) and Val (Columbia, SC), son Tim (Cape Coral, FL), and son / daughters in law Donna, Johnny, and Ellen; adoring grandchildren Addison, Max, Heidi; expected grandson Henry; siblings Sherry, Dave, and Mike with their spouses Bob, Cindy, and Nancy; his Boston Terrier dog Gronk; along with many nieces and nephews, and countless friends. He was preceded in death by his former wife Lorrie (2012).
A celebration of Tom’s life will be held in Massachusetts at a later date.
In lieu of flowers, it is Tom’s wish that you reach out to call an old friend and hug your loved ones often. If you wish, contributions may be made in Tom’s memory to any veteran organization or his favorite annual charity Toys for Tots (https://secure.toysfortots.org/).
As we say goodbye to our beloved Tom, we take comfort in knowing his spirit will forever be intertwined with the children and grandchildren he loved so much and the memories he created with all of us. His legacy of love, laughter, joy, humor, and adventure will always blossom in our hearts. Semper Fi, no one left behind!
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