Help Desk Technician Tier II

The Help Desk Tier II Technician at Mainstay Technologies, Inc. is a mid-level technical role focused on resolving more complex end-user and system issues. Working onsite in Manchester, NH, you will take ownership of tickets from triage through resolution, act as a key escalation point for Tier I, and apply structured troubleshooting to deliver consistent service across client environments.

Responsibilities

• Serve as a reactive technical resource for the Service Team’s client base by building familiarity with client environments, users, and business needs through shared documentation and team collaboration
• Own client issues from initial triage through resolution, maintaining a high-quality and consistent support experience
• 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
• Resolve intermediate to advanced technical issues across workstation, application, and basic infrastructure layers, including operating system issues and performance troubleshooting
• Provide Microsoft 365 administration support, including user management, mailbox issues, and licensing
• Provide Google Workspace administration support, including user management, Gmail issues, and shared drive and permissions troubleshooting
• Handle Active Directory and Entra ID administration, including user accounts, group policies, and permissions
• Troubleshoot network connectivity and devices, including VPN, wireless, and basic firewall concepts
• Support Line of Business application troubleshooting and coordinate with vendors when needed
• Perform hardware troubleshooting and coordinate repair or replacement
• Support macOS and MacBook troubleshooting and end-user support
• Analyze issues beyond Tier I by using structured troubleshooting methods to identify root cause and drive long-term solutions
• Escalate complex or high-risk cases to Tier III or Engineering with clear documentation and context
• Manage assigned ticket queues with emphasis on prioritization, ownership, and timely resolution
• Handle escalations from Tier I with appropriate follow-through and communication
• Maintain clear, detailed, and accurate documentation within tickets
• Ensure tickets are categorized, prioritized, and updated in alignment with company standards
• 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, collaborating with the broader team while sharing ownership of client work
• Manage workload across the team’s client base, balancing reactive requests with proactive follow-up
• Collaborate with other service roles to support alignment on client priorities and environment health
• Maintain and improve client documentation, including system configurations, environment details, and support procedures
• Identify gaps in documentation and take ownership of updating or creating content, ensuring changes are communicated and aligned with internal documentation ownership
• Contribute to process improvements by identifying inefficiencies, recurring issues, and opportunities for standardization
• Work with Help Desk Tier I to support escalations and share troubleshooting guidance
• 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
• Maintain accurate time entries aligned with company standards
• Prioritize workload based on urgency, impact, and client expectations
• Meet defined service level objectives and response expectations

Requirements

• 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 (or equivalent experience) preferred
• Experience working in an MSP environment strongly preferred
• 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 willingness to support and mentor Tier I technicians
• Continuous learning mindset with a desire to grow into more advanced technical roles

Technologies

• Microsoft 365
• Active Directory
• Entra ID
• Google Workspace
• Gmail
• TCP/IP
• DNS
• DHCP
• VPN
• ConnectWise
• Windows
• macOS
• MacBook

Physical Requirements

• Prolonged periods of sitting at a desk and working on a computer
• Must be able to lift 15 pounds at times