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June 23-24, 2025

Live! by Loews Hotel | Ballpark Village
799 Clark Avenue | St. Louis, MO 63102

The Gateway Superintendent Summit fosters collaboration, innovation and leadership as leaders exchange ideas, learn from experts and share best practices with fellow colleagues throughout the region. Connect with superintendents and industry professionals to grow your professional network and build valuable connections. 

Tim Elmore will serve as one of the keynote speakers and will share his expertise on generational diversity in the workplace and how to get the most out of the strengths of each age group on your team while fostering effective communications.  Other keynote speakers are Sara Boucek, J.D. and Dr. Matthew Montgomery.

 

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The Summit registration fee includes an evening at the St. Louis Cardinals game in a Party Suite and overnight accommodations at Live! by Loews hotel (across the street from the stadium) for added convenience. Meals and parking are also included in your registration fee.  

The summit will begin at 11:30 a.m. on Monday, June 23 and conclude by noon on Tuesday, June 24 maximizing your time invested in this valuable professional development event. 

Don’t miss this unique opportunity to be part of the Gateway Superintendent Summit filled with thoughtful presentations, interesting conversations and fun networking with your colleagues.  

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DR. TIM ELMORE | KEYNOTE SPEAKER

Tim Elmore is founder and CEO of Growing Leaders, a non-profit that equips students and young professionals around the world to become life-giving leaders. His work grew out of 20 years of serving alongside Dr. John C. Maxwell. Tim has appeared in The Wall Street Journal, the Washington Post, USA Today, Psychology Today, and he’s been featured on CNN’s Headline News, Fox Business, Newsmax TV and Fox and Friends to talk about leading multiple generations in the marketplace. He has written over 35 books, including Habitudes: Images That Form Leadership Habits and Attitudes, Eight Paradoxes of Great Leadership and A New Kind of Diversity: Making the Different Generations on Your Team a Competitive Advantage. Connect with Tim on Facebook at drtimelmore, Instagram at tim_elmore and X at timelmore.

 

Monday Afternoon Session:
Leading Multiple Generations 
People talk a lot about diversity today—ethnic, gender and income diversity. But there is an elephant in the room. A different kind of diversity exists: the diverse generations that serve on your team. Boomer faculty differs from Gen Z faculty members. Today’s workplace has four to five generations working together and far too often, we collide instead of collaborate. Explore the characteristics of each generation at work today and how to leverage them to be your competitive advantage. Too often we stereotype, taking mental shortcuts with young or old teammates. Gain practical strategies to bring out the best in each generation.

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SARA BOUCEK, J.D. | KEYNOTE SPEAKER
Sara Boucek is known for her direct advice and engaging personality. She started her career representing Boards of Education until being named General Counsel for the Illinois Association of School Administrators. During her years at IASA, Sara negotiated thousands of administrator contracts, advised the association on policies and legislative initiatives, and represented the association on numerous task forces and legislative matters. Sara is a sought-after speaker at state, local and national conferences on School Law, education reforms and administrative employment contracts. 

Tuesday Morning Session:
Legal Landmines & Leadership: What Superintendents Need to Know Now 
Sara will provide legal insight and practical strategies to help superintendents navigate today’s most pressing challenges. From employment law to student rights and board governance, Sara will unpack the most pressing legal and policy issues impacting public education. She will offer timely guidance and real-world strategies to help district leaders navigate risk, avoid legal pitfalls and lead with confidence in today’s complex landscape. 

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DR. MATTHEW MONTGOMERY | KEYNOTE SPEAKER
Dr. Matthew Montgomery has been the Superintendent of Lake Forest Elementary School District 67 and Lake Forest Community High School District 115 since July 2021. Under his leadership, the district passed a $105.7 million referendum in April 2023 to modernize Lake Forest High School's infrastructure and learning spaces. Committed to communication and community engagement, Dr. Montgomery led the development of the "Portrait of a Learner," collaborating with 150 community members to establish a K-12 vision anchored in academic excellence and essential competencies for students' future success. Building on this foundation, he initiated five-year strategic plans for both districts, involving diverse stakeholders to create actionable and measurable roadmaps for the future. Before his tenure in Lake Forest, Dr. Montgomery served as Superintendent of Revere Local School District in Bath, Ohio. He began his educational career as a high school science teacher advancing to principal roles. In July 2013, he was appointed Superintendent of Waterloo Local School District, focusing on enhancing the STEM curriculum. 

Tuesday Morning Session:
Building Strong Board Relations: Strategies for Success 
Gain practical strategies for fostering strong, productive relationships between superintendents and boards of education. Drawing on lessons learned from leading two distinct boards in Lake Forest, Illinois, the presentation offers real-world insights, tested approaches to navigating challenges and a framework for maintaining focus on student-centered outcomes. Through stories, tools and candid reflections, explore how shared vision, trust, communication and distributed leadership can create a foundation for effective governance and sustainable progress.