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Rudy Massimo, BA, MA.


In his role as president and founder of Rudy Massimo and Associates, Rudy brings over thirty years of experience working as a senior executive in business, education and non-profit sectors. Rudy has a a BA from Concordia University, and an Executive MA In Leadership from the University of Guelph. Rudy has exceptional strengths in external relations, leadership, philanthropy, and educational administration. Rudy leads by example, combining professional knowledge and skill with a vivid sense of fun and adventure. With a wealth of international experience, Rudy will help support you and your team in developing your own strong network of international relations. Rudy is a passionate advocate for authentic, team-and value-based leadership - and he is ready to lead you down your own path of success.

Rudy Massimo: Team

Rudy's Story

Rudy was born and raised in New York City and later moved to Montreal with his family. As a teenager, Rudy burned off his endless energy by immersing himself in a variety of competitive sports. He continued playing varsity sports in university, but he soon realized it was no longer fulfilling him, and turned his attention to outdoor adventures. When he turned 20, he took a mountaineering course with the National Outdoor Leadership School, which he says, changed his life. The combination of being in the outdoors and learning about leadership was a catalyst for how he continues to live his life.

Soon after being married, Rudy got his dream job. He became the Executive Director of Camp Kawartha, and within a year of arriving, he turned a summer operation into a year round Outdoor Education Centre. Today, Camp Kawartha is an award-winning, year-round facility dedicated to inspiring environmental awareness and stewardship. Rudy continues to support the organization as a volunteer. During his time at Camp Kawartha, he also founded Peak Adventures Inc, a company providing international adventure expeditions for students, adults and corporate groups.

After ten years of leading Camp Kawartha and Peak Adventure Inc, Rudy became the CEO of Outward Bound Canada and led the organization through significant restructuring and re-positioning, resulting in achieving its highest enrollment ever, and becoming one of the most successful and innovative outdoor experiential learning organizations in Canada. Rudy continues to serve as an advisor with Outward Bound International.

Rudy transitioned to independent schools after leaving Outward Bound, and made his mark as an external relations professional when he was the Director of Advancement and Chief Operating Officer at Lakefield College School. He was responsible for advancing the school through communications, public relations and fund raising. During his time at Lakefield, his team raised over $30 million for financial assistance and capital projects. It is also during this period that Rudy’s competitive drive kicked back in. Instead of team sports, he focused on long distance running and cycling. Over a few years, Rudy competed in countless marathons in North America, including the Boston Marathon on multiple occasions, and competing in several Ironman competitions. He says, “The long training runs or rides gave me time to think and process my thoughts, but more importantly, the time alone nourished my mind, body and soul.”

Rudy also spent eight years at Shawnigan Lake School, the largest boarding school in Canada, as the Director of External Relations and Advancement. As part of their recent $50 Million Centennial campaign, he facilitated one of the largest gifts given to a Canadian independent school. During his tenure at Shawnigan, Rudy was also able to find time for another one of his passions…working with students, in a coaching and advising capacity. He used his leadership role to develop and lead initiatives aimed at improving student success, either through academics, arts, service initiatives or athletics. 

Rudy is a dynamic leader with over 30 years of experience working in business, education and the non-profit sector. He has exceptional strengths in external relations, leadership development and charitable sector/educational administration. He is a passionate advocate for authentic, team based, inspirational and values based leadership.

He is an energized and innovative leader, excelling in fast-paced working environments. Rudy is also an accomplished public speaker, consultant and community advocate, described by colleagues as “committed, caring, skilled, enthusiastic and inspirational,” noting that his energy and enthusiasm are contagious. 

During his career, Rudy has received recognition by many organizations around the world for his outstanding leadership and volunteer service work. When Rudy is not working, you are likely to find him hiking on the local trails, cycling around Peterborough County or at home making his famous pizza for friends and family. 

Rudy Massimo: About
Rudy Massimo: Blog2 Custom Feed
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