John Tracy

The Montgomery Academy

Lead daily technology operations and long-range planning for a two-campus organization spanning 13 buildings, approximately 650 students, 130 employees, and an extended user community of 1000+.

• Lead a three-person department and serve as the primary technology advisor to senior leadership and trustees, balancing strategic planning, operational continuity, institutional risk, and hands-on technical execution.
• Own a diverse portfolio of enterprise and SaaS platforms, including identity, messaging, productivity, student and business systems, integrations, communications, security, and user-facing services; translate specialized workflows into durable organization-wide solutions.
• Administer approximately 1,100 Google Workspace accounts, groups, messaging, SSO, application integrations, access changes, and two-step verification; also support Microsoft 365 identity and MFA.
• Own a mission-critical information system (PowerSchool) serving approximately 750 active users across three operating divisions, including custom SQL and reports, integrations, scheduling, records, workflow configuration, family access, and data integrity; migrated the platform from on-premises hosting and reduced downtime to nearly zero.
• Manage approximately 900 Apple devices and migrated the fleet between MDM platforms; centralized policies and automation allow a three-person department to support a reliable, secure 1:1 environment.
• Direct network, Wi-Fi, internet, VPN, server, endpoint, telephony, web, and communications operations across two campuses; personally troubleshoot complex cross-system issues and coordinate vendors when escalation is required.
• Provide transparent, responsive service through a ticketing and knowledge-base platform handling 1,000 requests annually.
• Develop annual, three-year, and five-year roadmaps and allocate approximately $250K–$500K annually; lead procurement, vendor evaluation, contract negotiation, implementation partners, renewals, and hardware and system lifecycles.
• Established organization-wide two-step verification and stronger MFA across services, blocking unauthorized access following phishing attempts and supporting annual cyber-insurance requirements.
• Led a $348K, three-phase access-control and physical-security program across multiple facilities, coordinating requirements, vendors, phased implementation, communications, and adoption; reduced incidental theft from weekly occurrences to virtually none.
• Communicate outages, incidents, changes, risks, and required actions in plain language; develop documentation and deliver practical training for employees, students, families, and leadership.

The Montgomery Academy

Led the modernization and unification of technology across two campuses while partnering closely with administrators, faculty, and operational teams.

• Designed the organization’s first comprehensive wireless network and unified both campuses under shared standards, centralized dashboards, VPN-connected services, and seamless connectivity.
• Initiated the migration from on-premises email to cloud productivity services and moved device management from ad hoc processes to centrally governed MDM.
• Originated a 1:1 device program and authored its cost model, policies, lifecycle, management approach, procurement strategy, and phased implementation for iPads and MacBooks.
• Chaired a cross-divisional enterprise-platform evaluation that replaced fragmented tools with one consistent system; led stakeholder discovery, product evaluation, decision-making, rollout, training, and change management.
• Saved an estimated $50K+ in network licensing fees over six years by selecting sustainable infrastructure without perpetual licensing and eliminating duplicated systems.
• Led technology training and user education, building confidence and adoption across groups with widely varying technical comfort and needs.