Help Desk Technician Tier II

Mainstay Technologies; Manchester (NH); On-site; USD 65,000 - 90,000; Full time

Job summary

Mainstay Technologies is seeking a Tier II Help Desk Technician in the United States to provide advanced IT support for a diverse client base. You will own issues end-to-end from triage to resolution, focusing on Microsoft 365, Active Directory, Windows, and networking across desktop, apps, and basic infrastructure.

You’ll work in a collaborative service-delivery environment, maintain thorough documentation, and mentor Tier I staff while coordinating with vendors on more complex problems.

Qualifications

• 2–4+ years of experience in IT support within a managed services or similar environment.
• Proven ability to troubleshoot and resolve intermediate technical issues across workstation, application, and basic network layers.
• Experience supporting Microsoft 365, Active Directory, and Windows environments.
• Strong understanding of networking fundamentals (TCP/IP, DNS, DHCP, VPN).
• Experience working within a ticketing system (ConnectWise preferred).
• CompTIA A+, Network+, or equivalent certifications; Microsoft certifications preferred.

Responsibilities

• Take ownership of client issues from initial triage through resolution, ensuring a high-quality and consistent support experience.
• Resolve intermediate to advanced technical issues across workstation, application, and basic infrastructure layers.
• Assist with Microsoft 365 administration (user management, mailbox issues, licensing) and Google Workspace administration.
• Troubleshoot network connectivity issues (VPN, wireless) and coordiante with vendors as needed.
• Maintain accurate tickets with clear documentation and ensure proper categorization and prioritization.
• Collaborate with Systems Administrators, CTMs, and Engineering on complex issues and initiatives.
• Provide mentorship to Tier I technicians and contribute to process improvements.

Skills

Troubleshooting

Microsoft 365 administration

Active Directory

Windows environments

Networking fundamentals

VPN

ConnectWise

MacOS support

Root cause analysis

Documentation

Vendor coordination

Education

CompTIA A+

CompTIA Network+

Microsoft certifications

Tools

ConnectWise

Google Workspace

Microsoft 365 Admin

Job description

The Help Desk Tier II Technician is a mid-level technical role responsible for resolving more complex end-user and system issues, supporting the team’s client base, and serving as a key escalation point for Help Desk Tier I.

This role is focused on deeper technical troubleshooting, ownership of client environments, and delivering consistent, high-quality support across a wide range of technologies. The Help Desk Tier II Technician operates with a higher level of autonomy, judgment, and technical capability, ensuring issues are resolved efficiently while maintaining strong communication with clients and internal teams.

Tier II Technicians are not primarily responsible for live answer phone support; however, they may assist as needed during periods of high volume or team coverage gaps. Their primary focus remains on ticket-based work, escalations, and reactive engagement with the team’s client base to ensure stability and a strong overall service experience.

What You Will Do

Client Ownership & Service Delivery

• Serve as a reactive technical resource for the Service Team’s client base, building familiarity with client environments, users, and business needs through shared documentation and team collaboration

• Take ownership of client issues from initial triage through resolution, ensuring a high-quality and consistent support experience

• Build and maintain strong working relationships with client stakeholders, end users, and vendors

• Identify recurring issues, trends, or risks and communicate them to the appropriate internal stakeholders

Tier II Troubleshooting & Technical Resolution

• Resolve intermediate to advanced technical issues across workstation, application, and basic infrastructure layers, including:

• Operating system issues and performance troubleshooting

• Microsoft 365 administration (user management, mailbox issues, licensing)

• Google Workspace administration (user management, Gmail issues, shared drive and permissions troubleshooting)

• Active Directory and Entra ID administration (user accounts, group policies, permissions)

• Network connectivity and device troubleshooting (VPN, wireless, basic firewall concepts)

• Line of Business application troubleshooting and vendor coordination

• Hardware troubleshooting and coordination for repair or replacement

• macOS and MacBook troubleshooting and support, reflecting the growing share of Apple devices across client environments

• Analyze issues more deeply than Tier I, using structured troubleshooting methods to identify root cause and implement long-term solutions

• Escalate complex or high-risk issues to Tier III or Engineering with clear documentation and context

Ticket Management & Workflow

• Manage assigned ticket queues with a focus on prioritization, ownership, and timely resolution

• Handle escalations from Tier I, ensuring proper follow-through and communication

• Maintain clear, detailed, and accurate documentation within all tickets

• Ensure tickets are categorized, prioritized, and updated in alignment with company standards

Service Team Support Model

• Support the Service Team’s full client base as a reactive technical resource, providing consistent and knowledgeable technical support

• Operate within a Service Delivery Team structure, leveraging the broader team for collaboration, support, and escalation while sharing ownership of client work across the team

• Manage workload across the team’s client base, balancing reactive requests with proactive follow-up

• Collaborate with other service roles to ensure alignment on client priorities and environment health

Documentation & Continuous Improvement

• Maintain and improve client documentation, including system configurations, environment details, and support procedures

• Identify gaps in documentation and take ownership of updating or creating new content, ensuring changes are communicated and aligned with the appropriate internal stakeholders responsible for overall documentation ownership

• Contribute to process improvements by identifying inefficiencies, recurring issues, and opportunities for standardization

Cross-Team Collaboration

• Work closely with Help Desk Tier I to support escalations and provide guidance on troubleshooting approaches

• Collaborate with Systems Administrators, CTMs, and Engineering on more complex issues or initiatives

• Participate in team huddles, training sessions, and feedback loops to improve service delivery

Time Management & Accountability

• Maintain accurate time entries aligned with company standards

• Effectively prioritize workload based on urgency, impact, and client expectations

• Meet defined service level objectives and response expectations

Your Background

Required Experience and Skills

• 2–4+ years of experience in IT support within a managed services or similar environment

• Proven ability to troubleshoot and resolve intermediate technical issues across workstation, application, and basic network layers

• Experience supporting Microsoft 365, Active Directory, and Windows environments

• Strong understanding of networking fundamentals (TCP/IP, DNS, DHCP, VPN)

• Experience working within a ticketing system (ConnectWise preferred)

Preferred Certifications and Education

• CompTIA A+, Network+, or equivalent certifications

• Microsoft certifications (or equivalent experience) preferred

• Experience working in an MSP environment strongly preferred

Skills for Success

• Strong problem-solving skills with the ability to independently work through complex issues

• High level of ownership and accountability for client outcomes

• Ability to communicate technical information clearly to non-technical users

• Strong attention to detail in documentation and ticket management

• Ability to balance multiple priorities in a fast-paced environment

• Collaborative mindset with a willingness to support and mentor Tier I technicians

• Continuous learning mindset with a desire to grow into more advanced technical roles

Physical Requirements:

• Prolonged periods of sitting at a desk and working on a computer

• Must be able to lift 15 pounds at times