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. 

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 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) 
• 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 

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 

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 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 

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 
• 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 

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 

• 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 

About Mainstay 

Mainstay Technologies- IT you trust from a team you enjoy. Mainstay Technologies provides a full IT and Information Security department to small and medium-sized businesses in the northern New England area. As a company in the Best Companies to Work For Hall of Fame, we believe in using the power of technology and of business to help people flourish. This translates to a culture of caring, high-ownership teammates who work hard, enjoy each other immensely, and turn off the work at 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 means. In addition to being a Best Company to Work For, we have also been recognized for Coolest Companies for Young Professionals, “Best of Business” for Managed IT Services, and the Torch Award for Marketplace Ethics.  We have made the Inc. 500 | 5000 List for fastest growing small businesses 5 times.   

Benefits  

This is a full-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. 

We maintain a 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 not required. 

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  

We utilize an Applicant Tracking System for our applications. Please whitelist the following domains to ensure you receive our communications:  jazz.co, jazzhr.com, and applytojob.com