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Confidence * Focus * Commitment

Leadership Development

Rudy Massimo & Associates is an international consulting firm dedicated to the enhancement of personal and organizational effectiveness. We specialize in leadership development and fundraising consulting.

We are proud of the commitment and care we offer our clients. Each of our associates is a dynamic professional offering a wealth of experience and expertise. We are passionate about wanting to make a difference and thrive on being able to encourage and inspire individuals and organizations to reach their goals. As a team of associates we take pride in having the resources, knowledge and tools available to strategically lead during this unprecedented period of change.

Rudy Massimo & Associates understands what it takes to successfully achieve results, from raising millions of dollars for charity to climbing mountains. New levels of commitment, innovation and teamwork will be required if organizations want to continually improve and build upon their goals. We offer a proactive and challenging approach to learning what it takes to lead, as well as aligning and collaborating one's talent to a common purpose and vision. At Rudy Massimo & Associates our approach is simple and results oriented. We focus on building positive and healthy relationships.


  Rudy Massimo, BA, MA

Rudy has accumulated over 30 years of international experience working with businesses, educational oganizations, and the not-for-profit-sector providing leadership training, strategic planning, motivational speaking, and adventure-based programming. In July 2008, he launched Rudy Massimo & Associates, a firm specializing in leadership development, major gifts fundraising and executive coaching.

Rudy has demonstrated exceptional strengths in change management and leadership development. As the Director of Advancement at Lakefield College School (2002-2008) Rudy and his team raised over $30M for bursaries and capital projects. While CEO and Executive Director/Head of School at Outward Bound Canada (1997-2003), Rudy led the organization through significant restructuring and re-positioning, achieving the organization's highest student enrollment ever, and becoming one of the most successful and innovative outdoor experiential schools in Canada.

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

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