Desktop Team Supervisor

Madison Approach Staffing Inc; Town of Ossining (NY); On-site; USD 70,000 - 94,000; Full time

Job summary

Madison Approach Staffing Inc is recruiting for a Desktop Team Supervisor for our client, a mission‑based nonprofit organization. This full‑time, on‑site role requires leading desktop support operations, guiding performance, and acting as the escalation point for complex issues in a Windows and Apple environment.

The ideal candidate has 5+ years of helpdesk experience, 2+ years of supervisory experience, a CompTIA A+ certification, and an Associate degree in IT or equivalent.

Qualifications

• 2+ years of supervisory experience with performance evaluations and disciplinary actions
• 5+ years helpdesk experience
• CompTIA A+ certification
• Associate's degree in IT or equivalent
• Proficiency with Windows and Apple systems, M365, Intune, AD, Azure, and VPN
• Strong communication and problem-solving skills

Responsibilities

• Supervise desktop support team and conduct performance reviews
• Provide direction, coaching, and handle performance issues
• Allocate workload and distribute support tickets
• Hire, train, develop team members and mentoring
• Track incidents and maintain records; liaise with vendors
• Manage equipment inventory

Skills

Supervisory experience

Helpdesk experience

Leadership

Communication skills

Problem-solving

Education

Associate's degree in IT or equivalent

Tools

Windows

Apple macOS

Microsoft 365

Intune

Active Directory

Azure

VPN

Job description

Job Type: Direct Hire (Full-time, Regular)
Salary: $81,900 annually
Location: Northern Westchester, NY | FULL-TIME ON-SITE ONLY (Not Remote, Not Hybrid)
Schedule: Monday-Friday, 8:30am-4:00pm

Job Overview

Madison Approach Staffing is recruiting for a Desktop Team Supervisor for our client, a mission-based nonprofit organization. This full-time, on-site position requires an experienced supervisor to oversee desktop support operations, manage and evaluate team performance, and serve as escalation point for technical issues. The ideal candidate has 5+ years helpdesk experience, proven supervisory background with team management and employee evaluation skills, CompTIA A+ certification, and technical proficiency with Windows and Apple systems.

Key Responsibilities

Team Management & Supervision

• Supervise desktop support team; conduct employee evaluations and performance reviews
• Provide clear direction, coaching, and discipline; address performance issues
• Manage team workload, priorities, and support ticket distribution
• Hire, train, and develop team members; provide technical and professional development guidance
• Foster collaborative and efficient team environment

Technical Support & Problem Resolution

• Respond to user-reported issues and escalated support tickets
• Provide technical support for desktop hardware and software (Windows and Apple systems)
• Troubleshoot complex issues including viruses, diagnostics, file repair, and data encryption
• Administer Microsoft 365, Microsoft Intune, Active Directory, Azure, and VPN environments
• Provide AV setup and support for presentations and Teams meetings

Documentation & Operations

• Track, document, and resolve incidents with clear resolution notes
• Manage projects within desktop team's responsibility
• Maintain accurate records and work with technology vendors
• Manage equipment inventory and assignment

Required Skills & Experience

• Supervisory Experience: Proven 2+ years supervising IT team; demonstrated competency in employee evaluations, performance management, and disciplinary action
• Technical Experience: Minimum 5 years helpdesk experience
• Certifications: CompTIA A+ required
• Education: Associate's degree in IT or equivalent professional experience
• Technical Skills: Proficiency with Windows/Apple systems, Microsoft 365, Intune, Active Directory, Azure, VPN
• Leadership: Ability to mentor, coach, and manage team performance
• Communication: Clear verbal, written, and interpersonal skills
• Problem-Solving: Ability to solve moderate to high complexity technical issues

Preferred Skills & Experience

• CompTIA Network+ or Security+ certification
• Prior team lead/supervisory experience in helpdesk environment
• Device management and mobile device support experience
• Vendor management experience
• On-call support experience

IMPORTANT: Full-time on-site position only. No remote or hybrid options. On-call support and weekend hours as required. W-2 employee role only—no C2C or B2B solicitations.