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About the Role
Proactive Technology Group is seeking a technically strong, client-focused Technical Team Lead/Manager to manage a team of 4-6 help desk technicians, serve as the primary technical point of contact for clients, and assist with project work. This role requires advanced troubleshooting skills, strong leadership, and a commitment to delivering VIP-level client service.
Responsibilities
- Lead, mentor, and support a team of 4–6 help desk technicians.
- Oversee ticket queues, prioritize workloads, and ensure SLAs and service quality standards are met.
- Serve as the escalation point for the help desk team, providing technical guidance and coaching.
- Review documentation and ticket notes for accuracy and completeness.
- Identify recurring issues and drive process improvements across the team.
- Act as the main technical contact for assigned clients.
- Provide VIP-level support to executives and key client stakeholders.
- Build strong, trusted relationships with client contacts and understand their business needs.
- Clearly communicate progress, risks, and technical recommendations to clients and internal teams.
- Provide Level 2/3 support, onsite and remote, for issues involving workstations, laptops, peripherals, Microsoft 365, Entra ID, user account management, Windows Server, line-of-business applications, and network connectivity.
- Escalate complex issues to senior engineers or project resources when appropriate.
- Assist with project tasks such as network equipment installations and replacements, firewall and switch swaps, wireless deployments, endpoint deployments and refreshes, server and infrastructure upgrades, and office IT moves.
- Document work, technical findings, and client environment details in IT Glue.
- Use Halo PSA for ticket management, time entry, and work tracking.
- Use Ninja RMM for remote access, monitoring, and endpoint support.
Requirements
- Proven experience leading or mentoring technical staff.
- Deliver exceptional customer service and remain professional under pressure.
- Communicate clearly with executives, end users, and technical teams.
- Strong troubleshooting skills and ability to resolve complex issues independently.
- Organized, reliable, and able to balance team management with hands-on work.
- Adapt quickly to different client environments and technologies.
- Flexible with scheduling, as some after-hours or early-morning work may be required.
- 3–5+ years in a managed services or IT support role, including Level 2/3 support.
- Prior experience in a team lead, supervisory, or senior technician role.
- Experience supporting Microsoft 365, Windows 10/11, Windows Server, Azure and Entra ID environments, and network infrastructure including switches, firewalls, and wireless.
- Familiarity with technologies such as SonicWall, Meraki, UniFi, and Ruckus.
- Experience with IT documentation platforms and PSA/ticketing systems.
- Valid driver’s license and ability to travel to client locations as needed.
Skills
- Advanced troubleshooting
- Leadership
- Client service
- Microsoft 365
- Entra ID
- Windows Server
- Network connectivity
- Wireless
- Switching
- Firewalls
- IT Glue
- Halo PSA
- Ninja RMM
- SonicWall
- Meraki
- UniFi
- Ruckus
Location
- Greenvale, NY
- Manhattan
- Queens
- Brooklyn
- Long Island
Work Type
- Onsite
- Full-time
- Hybrid
Experience Level
- 3-5+ years in managed services or IT support
- Team lead/supervisory/senior technician experience
Salary/Compensations
- 80k-95k
Benefits
- 401(k)
- 401(k) matching
- Dental insurance
- Health insurance
- Life insurance
- Paid time off
- Parental leave
- Professional development assistance
- Referral program
- Vision insurance
About the Company
- Proactive Technology Group is an $8M+ managed IT services company serving mid-market businesses across the New York metro area.
- We are a growth-stage IT services platform with active expansion into cybersecurity compliance, AI consulting, and strategic acquisitions.
- Our team of 35 operates with an ownership mentality, powered by EOS and a culture that rewards initiative over tenure.
- We are actively acquiring, launching new service lines, and expanding our footprint.
- Operator culture: We run on EOS. Roles are clear. Accountability is real.
- Supportive team: 35 people who show up, do the work, and have each other's backs. Leadership is accessible. Wins are recognized. Development is funded.