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

Barbara Cohen, Chief Information and Innovation Officer at Brandeis Marin, joins the podcast to discuss independent school technology department staffing and leadership. Cohen shares strategies for modular job design, aligning technology initiatives directly with school mission, and facilitating constructive parent dialogues regarding student device usage and social health.

Brandeis Marin — An independent K–8 Jewish day school in San Rafael, California, where Barbara Cohen serves as Chief Information and Innovation Officer.

The Anxious Generation — Book by Jonathan Haidt utilized by Brandeis Marin for community-wide reading and dialogue on youth technology use and supervision.

The Six Types of Working Genius — Team assessment framework by Patrick Lencioni referenced for identifying individual natural talents and balancing organizational team dynamics.

DISC Profile — Workplace behavior assessment tool used by technology leaders to analyze team communication preferences and working styles.

Prizmah: Center for Jewish Day Schools — Network supporting Jewish day schools through peer cohorts, leadership development, and educational technology collaboration.

Dr. Tim Tillman, founder of Allied Cyber Academy, joins the pod to discuss bridging the gap between school technology leaders and governing boards. The conversation examines framing cybersecurity risk, defining digital duty, establishing disaster recovery plans, and managing emerging challenges like AI and vibe coding.

Allied Cyber Academy — Organization founded by Dr. Tim Tillman to train ed tech leaders, school boards, and superintendents on cybersecurity governance and risk management.

K12 SIX — Threat intelligence sharing community focused on preventing cyber incidents in K–12 schools.

Virginia Department of Education — State education agency where Dr. Tim Tillman previously served as Chief Information Security Officer.

In this episode, technology leaders discuss the integration of artificial intelligence in K-12 education with educator Douglas Kiang. The conversation examines essential skills for the AI era—including design thinking, close reading, and version control via GitHub—alongside data privacy considerations, the concept of distant writing, and evolving academic assessment models.

Douglas Kiang's Official Blog — The speaker's primary digital publication repository covering classroom workflows, design thinking, and the "AI Forward" series.

AP Computer Science Principles (College Board) — The advanced secondary curriculum framework for which Douglas Kiang served as a materials developer and independent project assessment architect.

GitHub — A software repository and version control platform integrated into the Menlo School curriculum to manage student multi-branching project workflows.

Google Workspace for Education — A secure productivity environment leveraged by school technology departments to keep user data in-house and isolated from external AI training datasets.

Perplexity AI — An information discovery and conversational search engine provided to high school students to enable multi-engine comparative analysis.

Google NotebookLM — A personalized AI research assistant noted for its widespread popularity among students evaluating internal course source documents.

ResearchGate: Distant Writing Paper — The scholarly publication by Professor Luciano Floridi of Yale University detailing the transition of authors into design directors.

Live from the ATLIS 2026 Annual Conference, the hosting team is joined by Alex Inman and Tom Wildman to analyze the evolving role of Managed Service Providers (MSPs) in independent schools. The conversation addresses the rise of fractional staffing, shifting IT reporting structures under CFOs, and the absolute necessity of cultural alignment when outsourcing school technology services.

• Knowing Technologies
• Educational Collaborators

Evan Harris of Pathos Consulting Group addresses the escalating risks of AI-generated deepfakes and companions within school communities. The discussion highlights the psychological tactics scammers use to bypass critical thinking, the limitations of technical detection tools, and the urgent need for schools to update policies and student safety protocols.

• Pathos Consulting Group - The organization founded by Evan Harris focused on deepfake safety and crisis readiness for schools.
• Reality Defender - A digital forensics tool mentioned for its use in identifying AI-generated content.
• KnowBe4 - A cybersecurity awareness platform discussed in the context of phishing and deepfake training.
• "Fake" by Perry Carpenter - A recommended resource for understanding the science of deception and human nature.
• Presidium - An organization cited for its data on the rise of youth-to-youth abuse within independent schools.
• Adaptive Security - A company providing cybersecurity training for high-stakes organizations.