Help Desk Technician Tier II

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 Technicianoperateswith a higher level of autonomy judgment and technical capability ensuring issues are resolved efficiently whilemaintainingstrong communicationwith clients and internal teams.

Tier II Techniciansare not primarily responsible for live answer phone support; however they mayassistas needed during periods of high volume or team coverage gaps. Their primary focusremainson ticket-based work escalations and proactive engagement with their assigned clients to ensure stability and a strong overall service experience.

Client Ownership & Service Delivery

• Serve as the primary reactive technical resource for assigned clients developing familiarity with their environments users and business needs
• Take ownership of client issues frominitialtriage through resolution ensuring a high-quality and consistent support experience
• Build andmaintainstrong working relationships with client stakeholders end users and vendors
• Identifyrecurring issues trends or risks and communicate them to theappropriate internalstakeholders

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)
• Active Directory and Entra ID administration (user accounts group policies permissions)
• Network connectivity and device troubleshooting (VPN wireless basicfirewallconcepts)
• 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 toidentifyroot 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 andtimelyresolution
• Handle escalations from Tier I ensuring proper follow-through and communication
• Maintain clear detailed andaccuratedocumentation within all tickets
• Ensure tickets are categorized prioritized and updated in alignment with company standards

Primary Client Support Model

• 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 structureleveragingthe broader team for collaboration support and escalation whilemaintainingownership 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

Documentation & Continuous Improvement

• Maintain and improve client documentation including system configurations environment details and support procedures
• Identifygaps in documentation and take ownership of updating or creatingnew content ensuring changes are communicated and aligned with theappropriate internalstakeholders responsible for overall documentation ownership
• Contribute to process improvements byidentifyinginefficiencies 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

• Maintainaccuratetime entries aligned with company standards
• Effectively prioritize workload based on urgency impact and client expectations
• Meet defined service levelobjectivesand response expectations
• Serve as the primary reactive technical resource for assigned clients developing familiarity with their environments users and business needs
• Take ownership of client issues frominitialtriage through resolution ensuring a high-quality and consistent support experience
• Build andmaintainstrong working relationships with client stakeholders end users and vendors
• Identifyrecurring issues trends or risks and communicate them to theappropriate internalstakeholders

Your Background

• Required Experience and Skills
• 24 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

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

About Mainstay

Mainstay Technologies- IT you trust from a team you enjoy. Mainstay Technologies provides a full IT and Information Security departmenttosmall andmedium-sizedbusinesses in the northern New England area. As a company in the Best Companies to WorkForHall of Fame we believe in using the power of technologyand ofbusiness to help people flourish. This translates to a culture of caring high-ownership teammates who work hard enjoy each other immensely and turn offthe workat the end of the workday to focus on what matters more than work.

It is our commitment to people that makes us who we are. We love what we do and we love who we do it with. We are driven by our mission: to give more than we get. People are always the ends never the addition to being a Best Company to Work For we have also been recognizedforCoolest Companies for Young Professionals Best of Business for Managed IT Services and theTorch Award for Marketplace Ethics. We have made theInc.Listfor fastest growing small businesses 5 times.

Benefits

This is afull-time salaried position with a full benefits package including:

• 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

Location

We believe in Work-from-Anywhere and in the value of in-person relationships. We offer strong flexibility to work remotely while also recognizing the importance of face-to-face connection through team meetings all-staff gatherings and in-person client meetings.

Wemaintaina beautiful office in Manchester NH as well as a satellite office in Laconia and we encourage each team member to choose the mix of home and in-office work that best supports their well-being and effectiveness. While coming into the office weekly is encouraged it is notrequired.

Because this role includes regular in-person client meetings applicants must live within driving distance of our clients offices and team events to support client relationships onboarding and ongoing collaboration.

Application

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