Technology Services and Training Supervisor

Technology Services and Training Supervisor

Job

Job Description

Provides leadership, supervision, and direction for the Technology Services and Training team, including Tier I Technology Services Specialists and Tier II Technology Services and Training Specialists. Oversees proactive user support programs, technology training initiatives, service coordination with schools, and continuous improvement efforts to enhance staff and student technology experiences. Serves as the division-wide point of accountability for frontline support quality, user engagement, communications, and operational readiness.

Works closely with school administrators, department leaders, and IT teams to ensure effective, consistent, and preventative technology support practices across all sites.

• Bachelor's degree in information technology, computer science, instructional technology, or a related field; and three (3) years of progressively responsible technical support experience, including experience providing training, conducting user support, or leading technical teams; or any equivalent combination of training and experience which provides the required skills, knowledge, and abilities.
• Supervisory experience preferred.

• Valid Virginia driver's license and insurability required.
• This position requires routine travel to and from multiple York County School Division locations as part of the regular duties and responsibilities.

• Knowledge of modern instructional and administrative technology systems used in K–12 environments.
• Knowledge of IT service delivery models, including incident management, problem management, and proactive support frameworks.
• Knowledge of end-user training methodologies, adult learning strategies, and user-readiness best practices.
• Ability to supervise and mentor Tier I and Tier II staff, including assigning work, monitoring performance, and providing coaching and feedback.
• Ability to analyze support trends, identify root causes, and develop preventative strategies that reduce ticket volume.
• Ability to collaborate with school administrators, teachers, and staff to understand needs and improve technology adoption.
• Ability to communicate clearly with both technical and non-technical users.
• Ability to create user-friendly training materials, documentation, and communication.
• Ability to maintain effective, professional working relationships with IT staff, school staff, vendors, and leadership.
• Strong customer-service orientation and ability to foster a positive support culture.
• Ability to manage multiple priorities, plan team workflows, and coordinate division-wide technology initiatives.
• Ability to deliver structured training and coaching to users with varying skill levels.
• Skill in identifying and analyzing trends in recurring issues to develop preventative strategies.
• Ability to establish and maintain effective, professional working relationships with IT staff, school staff, and customers.
• Ability to support virtual desktops, remote application access, and Apple devices.
• Ability to communicate technical information clearly to both technical and non-technical users.
• Ability to prepare documentation, training materials, reports, and analysis.
• Ability to stay current with emerging technologies and propose proactive improvements.
• Strong listening skills, customer-centered approach, and the ability to work independently or collaboratively.
• Ability to respond effectively to emergency situations.
• Ability to verbally communicate via telephone.
• Visual acuity and perception required for operating a motor vehicle and working with computer hardware and software.
• Ability to stoop, kneel, bend, and reach when working with electronic equipment, and to lift fifty (50) pounds unassisted.
• Ability to grasp, hold, and manipulate tools and electronic parts.
• Ability to climb a ladder while carrying twenty-five (25) pounds unassisted.

• Provides daily supervision, guidance, and performance management for Tier I and Tier II specialists.
• Oversees scheduling, workload distribution, site coverage, and priority assignments.
• Conducts evaluations, develops staff growth plans, and ensures ongoing professional development.
• Provides coaching, mentoring, and technical guidance to improve team effectiveness.
• Leads the division's proactive support strategy, including routine school visits, staff outreach, and preventative system checks.
• Ensures team members identify and address issues before they become service interruptions.
• Oversees user-readiness initiatives, including new-staff onboarding, technology workshops, and general technology competency programs.
• Coordinates division-wide technology training for staff, including in-person, virtual, group, and one-to-one delivery.
• Oversees development of training materials, user guides, and knowledge-base resources.
• Ensures Tier II staff provide advanced training support and mentorship to Tier I staff.
• Serves as…