Gary Philip Singer

LYMAN – Gary Philip Singer passed away on Jan. 25, 2023 at the age of 76 following a brief illness. Gary was born on July 20, 1946, in Boston to Samuel and Helen (Ackerman) Singer.

He grew up in Dorchester and graduated from Boston Latin School in 1964. He received a BA in math from McGill University in Montreal in 1968. During the Vietnam War he served in the US Army Reserves and the Maine National Guard.

He first came to Maine in December 1969 for a job as an actuary with Union Mutual Life Insurance Co. He designed and programmed in Fortran a management information system giving the company extensive information about the experience of their disability income policies. The company became the leader in the industry in this product line. While there, he met his wife Paula (Noyes) Singer when they worked on a computer system together.

Following a move to Norwood, Mass. in 1979, Gary was in charge of computer operations for several major corporations including H.P. Hood, Howard Johnson’s, and Plymouth Rock Assurance Corporation. At Howard Johnson’s he successfully designed and installed two IBM computers, the network and the software associated with the migration of their reservation system in-house, a feat featured in Computer World.

In 1994, Gary joined with his wife Paula (now a tax lawyer) in founding Windstar Technologies, Inc. to provide sophisticated software for dealing with the complex federal tax rules and procedures companies had to follow when making payments to foreign students and scholars. They grew the company to serve more than 450 client sites at colleges, universities, teaching hospitals, research institutes and the Library of Congress.

Gary liked working with tools and had many projects, including building a new deck. He always had many challenging hobbies. He took up snorkeling and then scuba diving, becoming certified on The Wall off Grand Cayman Island. He was an avid ham radio operator, becoming proficient in Morse code at 20 words per minute. For better reception, he had a 50-foot tower installed in the back yard. He became an avid sailor safely piloting their successive sailboats and their trawler through the dangers of Boston Harbor, as well as the coasts of Massachusetts and Maine (in the fog). He took up nature photography, traveling to Lubec to photograph the Puffins on Seal Island, a trip which triggered their retirement to Maine upon the sale of their company to Thomson Reuters in 2011. Gary was also an avid duplicate bridge player and with his partner, Paula, took up bridge again during their retirement after a 30-year hiatus from playing. They won the Maine State Championship in their class in 2016.

He is survived by his mother (now 100 years of age) of Potomac, Md.; his wife of 46 years, Paula; his daughter, Samantha Singer and her husband Kevin Spencer, of Longmont, Colo.; his stepdaughter, Beth Goodrich, her husband, Kevan Whitten, and their twin daughters, Grace and Rose Whitten, of Lyman; his brother, Stephen Singer and his wife,Janet of Merrimack, NH, his brother, Dr. Richard Singer and his wife Miriam of Potomac, Md.; and numerous nieces, nephews, grand-nieces and grand-nephews.

Gary spent the last three months of his life at Avita of Wells. The family will be forever grateful for the loving care he received from their staff and from the hospice staff of Compassus.

A visitation will be held on Sunday, Jan. 29, 2023, from 1 p.m. to 2 p.m. with a celebration of his life from 2 p.m. to 3 p.m. at Bibber Memorial Chapel, 67 Summer Street, Kennebunk, ME 04043. Come casually and bring your stories to share. A private burial with take place at Goodwins Mills Cemetery at a later date.

To leave a message of condolence, please visit Gary’s Book of Memories at

Arrangements are entrusted to Bibber Memorial Chapel, 67 Summer St. Kennebunk.

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