In this episode, Jason Epstein, TLIS, from the Berkshire School unpacks the evolving, around-the-clock responsibilities of technology leadership in a boarding school setting. Listen in to learn practical strategies for cross-training small IT teams, managing third-party vendor risks, and maintaining work-life balance amid relentless operational demands.

Jason on LinkedIn

Berkshire School — The independent boarding school located in Massachusetts where guest Jason Epstein currently serves as the director of technology.

ISTE — The International Society for Technology in Education, an organization Epstein has been involved with since his early days in education.

MassCUE — The Massachusetts organization for computer-using educators, mentioned as a key regional networking group for technology professionals.

Veracross — The student information system utilized at the Berkshire School and managed day-to-day by their registrar.

Naviance — A college counseling platform managed independently by the school's college counseling office.

Canvas — A learning management system cited during a discussion about the importance of evaluating third-party cybersecurity vulnerabilities.

Angela Mackenzie, Director of Innovation and Learning Technologies at Saint Margaret's Episcopal School, discusses unifying library services, educational technology, and computer science. She shares insights on managing AI adoption, maintaining data privacy during vibe coding experimentation, building faculty trust, and launching student-led innovation programs for emerging technologies.

Saint Margaret's Episcopal School — Independent preschool through grade 12 school located in San Juan Capistrano, California.

Google Gemini — Enterprise AI platform utilized by the school to protect data privacy during staff operations.

School AI — AI tool designed for safe educational interaction in elementary grade levels.

Claude by Anthropic — AI assistant used by Mackenzie’s faculty for advanced text processing and vibe coding experimentation.

Google NotebookLM — AI research and note-taking platform

Otter.ai — Speech-to-text audio transcription service

April Mardock, Chief Information Security Officer at WASIPC, joins the podcast to analyze the primary entry points targeted in K-12 ransomware incidents. The discussion offers actionable guidance on multi-factor authentication, vendor risk management, data retention policies, and using gamified tabletop exercises to prepare school leadership for cyber incidents.

• April’s LinkedIn profile and email address
• Cybersecurity tabletop simulation game (Gemini Gem), step into the hot seat of a live cyber attack and lead your team to safety
• I Asked 24 Ransomed School Districts How the Attackers Got In - There Were Only Three Answers, LinkedIn article that April authored
• K-12 SIX (K-12 Security Information Sharing and Analysis Center), threat intelligence community providing free K-12 cybersecurity guidance, checklist guides, and standards
• WISPC, public, non-profit agency in Washington state that provides technology solutions, data management, and cooperative purchasing services to K-12 schools
• Cyberforce|Q service from WISPC, building and implementing cybersecurity programs for organizations of all sizes
• Bluum service from WISPC, helping educators leverage technology to create a more effective and engaging student experience
• Cybersecurity & Infrastructure Security Agency (CISA), from the U.S. Department of Homeland Security; as the national coordinator for critical infrastructure security and resilience, CISA works with partners at every level to identify and manage risk to the cyber and physical infrastructure that Americans rely on every hour of every day. CISA works with partners to defend against today’s threats and collaborate to build a more secure and resilient infrastructure for the future.
• Secure Cloud Business Application (SCuBA), CISA project providing tailored cloud solutions guidance and secure configuration baselines (SCBs) for Microsoft 365 and Google Workspace applications. SCuBA’s guidance aims to protect information that organizations create, access, share, or store in cloud environments.
• Backdoors and Breaches, incident response card game