Registration and Continental Breakfast

Chesapeake Prefunction and Chesapeake Salon A

Opening Remarks

Chesapeake Salon B

Brian Cohen, Vice President, Center for Digital Education

Generative AI in K-12 — Risks and Opportunities

Chesapeake Salon B

This opening session frames the day by exploring both the promise and perils of Generative AI in K-12 education. We will look at how AI can streamline operations, personalize learning, and support teachers—while also surfacing the challenges of data privacy, ethics, and equity. Superintendents and leadership teams will leave motivated to consider how AI strategy fits into their district’s vision.

Key Takeaways:

Moderator: Tom Ryan, Senior Fellow Center for Digital Education

Networking Break

Chesapeake Salon A

Maryland’s AI Assessment: Implementation Guidance and Next Steps

Chesapeake Salon B

Join MSDE as we unveil our AI Implementation Guidance framework designed to support safe and effective AI Guidance. This interactive session brings together community stakeholders and LEA leaders to examine real-world applications and challenges while shaping Maryland’s path forward. Your expertise and feedback are essential as we work together to refine our statewide approach and ensure it meets the diverse needs of Maryland’s students and educators. Together, we’ll review the framework that positions Maryland as a national leader in the responsible implementation of AI in education.

Key Takeaways:

Moderator: Brian Cohen, Vice President, Center for Digital Education

Shawn Fritz-Rushing, Assistant State Superintendent, Maryland State Department of Education (MSDE)

Richard W. Kincaid, Assistant State Superintendent, Division of College and Career Pathways, Maryland State Department of Education (MSDE)

Chris Russo, National Director of SLED, Arctic Wolf

Erin E. Senior, Director of the Digital Learning Experience, Division of College and Career Pathways, Maryland State Department of Education (MSDE)

From the Field: Lessons Learned from AI Missteps

Chesapeake Salon B

No leader wants to reinvent already made elsewhere. This session draws on candid stories from districts that stumbled — whether through vendor overpromises, staff resistance, privacy pitfalls, or failed pilots. The emphasis is on what leaders would do differently next time and how to build safeguards that prevent missteps.

Key Takeaways:

Moderator: Brian Cohen, Vice President, Center for Digital Education

Peter Kaplan, SLED Capture Director – Government, Fortinet

Lunch

Please enter the buffet line in Chesapeake Prefunction and return to Chesapeake Salon B for seating.

Using the AI Maturity Tool to Drive Districtwide Readiness - Part 1: Understanding the AI Maturity Tool

(Leadership Track)

Chesapeake Salon B

Artificial Intelligence is rapidly reshaping the K-12 landscape—impacting classrooms, operations, and governance. Districts that wait risk being caught unprepared by vendor promises, legislative mandates, or community pressure. This session introduces superintendents and leadership teams to the CoSN/CGCS AI Maturity Tool, a framework designed to help districts assess their readiness and build an actionable AI strategy.

The tool spans **seven domains—leadership, technical infrastructure, security, operations, AI literacy, and data—**offering a comprehensive roadmap for district AI planning. Superintendents will see how the tool can anchor conversations with boards, staff, and community stakeholders, ensuring that AI adoption advances district goals responsibly and strategically.

Key Takeaways:

Co-Moderators:

Brian Cohen, Vice President, Center for Digital Education

Tom Ryan, Senior Fellow Center for Digital Education

Using the AI Maturity Tool to Drive Districtwide Readiness - Part 2: Building a Cross-Functional AI Leadership Team

(Leadership Track)

Chesapeake Salon B

Strategy without structure stalls. Using Domain 1: Leadership from the AI Maturity Tool, this session equips superintendents to build a cross-functional district AI leadership team. The team’s charge: to establish policies, standards, and implementation plans that harness AI’s power while safeguarding equity, security, and instructional quality.

Participants will explore critical leadership focus areas—including executive readiness, policy development, legislative alignment, and equity—and learn how to identify the right mix of instructional and operational voices at the table. Leaders will also sharpen their ability to become discerning AI customers, ensuring vendors deliver on promises without exposing the district to unnecessary risk.

Key Takeaways:

Co-Moderators:

Brian Cohen, Vice President, Center for Digital Education

Tom Ryan, Senior Fellow Center for Digital Education

Short Break

The Next 12 Months with AI: Urgent Priorities for Maryland Superintendents

Chesapeake Salon B

Generative AI is not on the horizon — it is already embedded in the platforms Maryland students and staff use daily, from Microsoft Copilot to Google Gemini. Over the next 12 months, these tools will transform instruction, operations, and district security whether leadership is ready or not.

This session provides Maryland superintendents with a focused view of the four most urgent disruption areas:

Participants will analyze real-world use cases, engage in superintendent-level scenario discussions, and leave with a practical Maryland-specific checklist of immediate steps. These actions align with MSDE’s AI needs assessment, procurement standards, and equity commitments. The message is clear: Maryland superintendents must act now to reduce risk, protect students, and position their districts to lead responsibly.

Key Takeaways:

Co-Moderators:

Brian Cohen, Vice President, Center for Digital Education

Tom Ryan, Senior Fellow Center for Digital Education

Panelists:

Kara Keller, Account Executive, MagicSchool

From Insights to Action: Turning AI Learning into District Leadership Priorities

Chesapeake Salon B

The real test of a professional learning day is not what you learned — but what you will do tomorrow. This highly interactive closing session ensures superintendents leave with clarity and commitment.

Participants will first reflect on the day’s sessions, capturing 3–10 takeaways that matter most for their district. Using a simple Impact vs. Effort framework, they will evaluate and prioritize these insights, surfacing the actions that will deliver the greatest value with the least complexity.

The session concludes with a superintendent report-out, where several leaders share their top priorities aloud. This creates peer learning, accountability, and momentum for statewide action.

Key Takeaways:

Co-Moderators:

Brian Cohen, Vice President, Center for Digital Education

Tom Ryan, Senior Fellow Center for Digital Education

End of Conference

Conference times, agenda, and speakers are subject to change.