.png?sfvrsn=a1439f00_1 "Bob Nicholson")
The Will J. Hancock Unsung Hero Award is given to business officers who have made extraordinary contributions to their schools and exemplify exceptional integrity, knowledge and motivation. At the end of each school year, new Unsung Heroes receive their award from their head of school, often at a significant school occasion such as a board meeting or an all-school ceremony. What makes these Unsung Heroes so special? The highlights below come straight from their colleagues' nominations.
Stay tuned throughout the summer for additional profiles. See the full list of 2026 recipients.
Title: Chief Operating Officer
School: Holy Trinity School, Richmond Hill, ON
Years at School: 10
Superpower: Innovation Catalyst: Bob Nicholson played a pivotal role in creating the Global Online School, an innovative virtual high school program for students in Grades 9–12. Launched in September 2023, the program offers flexible online learning combined with personalized mentorship. As the first program of its kind in Canada, the Global Online School has expanded Holy Trinity’s reach and created significant opportunities for new revenue growth.
Paperless Pro: Head of School Amanda Kennedy attributes Nicholson as the driving force and visionary behind the school’s transition to a paperless business office in 2022–23. By implementing an automated, real-time financial management system, he improved efficiency, increased financial transparency, and equipped budget managers with self-service access to budget data, enabling more informed planning and decision-making.
He is a servant leader, who models the school values and sense of community, always selfless and humble.
Endowment Steward: As a member of the school’s finance and operational risk committee and investment committee, Nicholson has been instrumental in growing the school’s investment portfolio by 50% and the school’s endowment by 60%.
Servant Leader: Nicholson “is a servant leader, who models the school values and sense of community, always selfless and humble,” said Kennedy. “You would never know that he had a glamorous career in professional sports management ... What you see is a COO who loves getting down on one knee to greet lower school students out front every morning and dressing up for Halloween as the purple 'fear' character from the movie ‘Inside Out.’”
He inspires great loyalty, both through his leadership and to the institution. He is not just a COO, but a leader, mentor and role model.
Home Run Career: Prior to Holy Trinity School, Nicholson served as the executive vice-president and COO of the Toronto Blue Jays for 18 years; as CFO of the Montreal Expos and Washington Nationals for five years; and as president and CEO of the Toronto Argonauts, in the Canadian Football League, for three years. At Holy Trinity, Nicholson delayed his retirement by a couple years to build an effective succession plan that ensures a smooth transition both for the new head of school, and to allow for a thorough search for his successor.
Legacy Leader: “The vast majority of Bob’s team have been at the school for a decade or more,” noted Kennedy. “He inspires great loyalty, both through his leadership and to the institution. He is not just a COO, but a leader, mentor and role model.”
