Help Desk Technician Tier II

Mainstay Technologies, Inc.•Manchester, NH

1d•Hybrid

About The Position

The Help Desk Tier II Technician is a mid-level technical role responsible for resolving more complex end-user and system issues, supporting assigned primary clients, 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 proactive engagement with their assigned clients to ensure stability and a strong overall service experience.

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)
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
Prolonged periods of sitting at a desk and working on a computer
Must be able to lift 15 pounds at times
Applicants must live within driving distance of our clients, offices, and team events to support client relationships, onboarding, and ongoing collaboration.

Nice To Haves

CompTIA A+, Network+, or equivalent certifications
Microsoft certifications (or equivalent experience) preferred
Experience working in an MSP environment strongly preferred

Responsibilities

Serve as the primary reactive technical resource for assigned clients, developing familiarity with their environments, users, and business needs
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
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), 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
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
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
Support a defined set of primary clients as the primary reactive technical resource, providing consistent and familiar technical support
Operate within a Service Delivery Team structure, leveraging the broader team for collaboration, support, and escalation while maintaining ownership of assigned client work
Manage workload across assigned clients, balancing reactive requests with proactive follow-up
Collaborate with other service roles to ensure 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 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
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
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

Benefits

A flexible and fun work environment with events, lunch+ learns, ping pong, snacks, games, and books
3 weeks of PTO (4 weeks after 2 years) per year
A 2-week sabbatical at 5 years and a 5-week sabbatical at 10 years
Health, Dental, and Vision Insurance
Disability Insurance
Group and Supplemental Life Insurance
Paid Family Leave
401(k) with 3% match
ESOP!
Team Profit Sharing
Training program (including paid certifications, tuition reimbursement, and bonuses on achieving certs)
Paid Volunteer Time Off