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Expanding horizons.

Our Focus

Rudy Massimo & Associates delivers leadershipphilanthropic and educational consulting services. Our mission is to share our industry knowledge with enthusiasm, authenticity and a forward-thinking mindset. We appreciate that growth is a continual process and we are committed to helping you perpetuate that growth into undiscovered horizons. Whether you are a small not-for-profit, a local business, a large corporation or an educational institution, we can help you reach new levels of success.


Philanthropic Consulting

We offer philanthropic consulting in a variety of charitable sectors.  We have a deep understanding of fundraising, in combination with relevant international experience, all while working collaboratively with industry leaders to support you. We approach fundraising in a unique, and value-based manner to help ensure the success of your organization.

Leadership Development

We offer leadership development for both professional and personal growth. We believe that a commitment to, and an investment in leadership development will have a significant positive impact on the effectiveness of your organization. Working with our leadership consultants and certified executive coaches, we can provide specialized coaching and mentoring with a focus on the leadership competencies that are required to be successful. We have extensive experience working with senior leaders and their teams, and can deliver tailored programs based on assessment, one day workshops and multi-day retreats.

Similing Team
Outdoors Meeting

Educational Services

We offer consulting services to educational institutions around the world. Some of these consulting services include; accreditation and inspection preparation, mentoring and coaching for educational leaders, and assistance with the start up of new schools. In addition, we also work with students and their families to address individual educational goals and create personalized plans for continued success as students progress through their academic careers.

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“Ultimately, leadership is not about glorious crowning acts. It’s about keeping your team focused on a goal and motivated to do their best to achieve it, especially when the stakes are high and the consequences really matter. It is about laying the groundwork for others’ success, and then standing back and letting them shine.”

Chris Hadfield, Astronaut and Former Commander of the ISS

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Meet Rudy

President and Founder


Rudy has made his mark as an industry leader in philanthropy, leadership development and educational consulting. Rudy has an innate ability to revitalize an organization's foundational leadership and foster lasting relationships both internally and externally. Rudy can help transform and diversify your team; build on existing competencies and develop a sustainable plan for growth. In his former roles as Chief Executive Officer, Chief Advancement Officer, Director of Advancement, and Head of External Relations, Rudy has facilitated more than $100 million in Major Gifts. Currently, Rudy is the volunteer Chair of the Principal Gifts Cabinet for JDRF's '$100 million Campaign to Accelerate', their largest fundraising initiative to date. 


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