Michael Kessler
Thinkers Facilitator
Michael brings more than 30 years of leadership experience as a founder, CEO, board member, and advisor across the education technology and non-profit sectors. He retired in 2025, hanging
up his CEO boots after building and leading multiple successful software companies, most notably MyVideoSpot, a nationally adopted video platform serving school districts, state education agencies, non-profits and small businesses across the U.S.
Over the course of his career, Michael focused on helping organizations grow, building strong teams, navigating change, and scaling ideas into sustainable, multi-million-dollar businesses. He worked closely with a diverse mix of customers and led initiatives spanning strategy, operations,
finance, governance, and business development.
Michael has also served on a variety of non-profit boards and advisory councils, supporting missions centered on education access, community impact, and workforce development. Now retired from day-to-day operations, he enjoys staying involved in a more hands-on way by
mentoring and helping tomorrow’s leaders build clear strategies and think thoughtfully about what’s next.
Outside of work, Michael enjoys traveling with his wife of 40 years, running a travel blog focused on cruising, and unwinding in his workshop welding, fixing, and tinkering with projects of all kinds.
Michael’s Facilitator Strengths:
Michael’s Facilitator Strengths:
Strategic Perspective – Helps leaders zoom out, connect the dots, and draw conclusions with both short-term execution and long-term vision in mind.
Growth-Minded – Experienced in scaling organizations and navigating change, while keeping people and culture at the center.
Collaborative Connector – Brings people together, encourages peer learning, and leverages the collective experience in the room.
Practical & Grounded – Focused on real-world application, accountability, and actionable takeaways—not theory for theory’s sake.
Michael’s Professional Highlights
1. Founder and CEO of multiple education technology companies with national and international adoption
2. Built and led several multi-million-dollar organizations over a 30+ year career
3. Board member and advisor to nonprofit, education, and civic organizations
4. Extensive experience in corporate governance, fundraising, workforce development, and community engagement

