Senior Support Technician

Role Title: Senior Support Tech

Company: Hometown Tech

Location: Wisconsin (within ~30 miles of Sharon, WI)

Employment Type: Full-Time, Salaried

Reports To: President

Directed By: System Architect

Role Summary

The Senior Support Tech provides expert-level IT support, systems administration, troubleshooting, and technical implementation for Hometown Tech’s business, school, and municipal clients. This role serves as a primary escalation point for complex technical issues and is expected to independently diagnose and resolve nearly any support or infrastructure problem encountered within established client environments.

The Senior Support Tech works across desktop, server, network, Microsoft cloud, domain, hybrid, endpoint management, and other client systems. This position is expected to take ownership of difficult technical problems from initial investigation through final resolution, involving the System Architect primarily when architectural decisions, major security considerations, or changes outside established standards are required.

A key expectation of this role is to look beyond immediate fixes. The Senior Support Tech should identify root causes, recognize recurring or systemic problems, and recommend or implement long-term solutions that improve reliability, security, manageability, and the overall client environment.

The Senior Support Tech is also expected to independently install, configure, migrate, and deploy new systems according to established specifications, implementation plans, and Hometown Tech standards.

This position is well suited for a highly experienced IT professional with broad technical knowledge, excellent troubleshooting instincts, strong personal accountability, and the ability to operate independently in a fast-paced small business environment.

Key Responsibilities

• Independently troubleshoot and resolve complex hardware, software, network, server, cloud, identity, endpoint, and infrastructure issues
• Serve as a primary escalation point for Support Techs and Advanced Support Techs
• Take ownership of difficult technical issues and drive them through diagnosis, resolution, documentation, and follow-up
• Perform root-cause analysis and identify long-term solutions rather than relying solely on temporary fixes or workarounds
• Identify recurring technical problems, inefficiencies, and risks and recommend changes that improve client environments
• Administer and troubleshoot Microsoft cloud and domain-based environments, including Microsoft 365, Microsoft Entra ID, on-prem Active Directory, and hybrid deployments
• Troubleshoot complex authentication, access control, synchronization, DNS, DHCP, Group Policy, device compliance, identity, and cloud service issues
• Configure, administer, and troubleshoot Microsoft Intune and other endpoint management systems
• Support and troubleshoot Windows servers and related infrastructure
• Administer and troubleshoot Google Workspace environments
• Troubleshoot and support network infrastructure involving firewalls, gateways, switches, VLANs, VPNs, routing, DNS, Wi-Fi, and related technologies
• Independently install and deploy workstations, servers, networking equipment, cloud services, and other client systems according to approved specifications and implementation plans
• Execute system migrations, infrastructure upgrades, equipment replacements, and new system deployments
• Validate completed installations and deployments to ensure systems operate according to specifications
• Troubleshoot interactions between multiple systems, vendors, applications, and infrastructure components
• Provide technical guidance, mentoring, and troubleshooting assistance to Support Techs and Advanced Support Techs
• Assist other technicians in developing troubleshooting approaches that address root causes rather than symptoms
• Participate in project implementations under the direction of the System Architect
• Identify situations requiring architectural, security, or design decisions and escalate those decisions to the System Architect when appropriate
• Communicate directly with clients regarding complex technical problems, recommendations, implementation activities, and resolution status
• Create and maintain accurate technical documentation, implementation notes, procedures, and client environment information
• Follow Hometown Tech standards, security requirements, documentation practices, and implementation procedures
• Travel regularly to client sites in Walworth County and surrounding areas
• Participate in an on-call rotation as needed to support client needs

Knowledge & Skills

• Expert troubleshooting and analytical problem-solving skills
• Broad understanding of IT infrastructure, systems administration, networking, cloud services, endpoint management, and end-user computing
• Strong working knowledge of Microsoft 365 and Microsoft Entra ID
• Strong working knowledge of Active Directory, Group Policy, DNS, DHCP, authentication, permissions, and hybrid Microsoft environments
• Strong experience with Microsoft Intune and modern endpoint management
• Strong understanding of networking concepts including firewalls, routing, switching, VLANs, VPNs, DNS, DHCP, and Wi-Fi
• Experience supporting Windows server environments and common server infrastructure
• Working knowledge of Google Workspace administration
• Ability to troubleshoot unfamiliar technologies using documentation, logs, testing, research, and systematic analysis
• Ability to identify the underlying cause of a problem rather than addressing only its immediate symptoms
• Ability to evaluate whether an existing solution is sustainable and recommend a more reliable long-term approach when appropriate
• Ability to independently execute technical installations and deployments from specifications, documentation, and implementation plans
• Ability to recognize when a technical issue requires an architectural or security decision outside the scope of an established implementation
• Ability to prioritize and manage multiple complex technical issues independently
• Ability to clearly communicate complex technical concepts to both technical and non-technical users
• Strong documentation, organizational, and attention-to-detail skills
• Strong initiative, accountability, professional judgment, and willingness to continue learning new technologies

Experience & Education

• Minimum of 8 years of professional IT support, systems administration, infrastructure, managed services, or comparable technical experience
• Significant experience independently troubleshooting complex technical issues
• Experience supporting Microsoft 365, Microsoft Entra ID, Active Directory, and hybrid Microsoft environments
• Experience implementing and supporting business networks, endpoint management systems, servers, and cloud services
• Experience performing system deployments, migrations, upgrades, or infrastructure installations
• Managed services or multi-client IT experience strongly preferred
• Relevant Microsoft, networking, security, or other industry certifications are preferred but not required
• Equivalent professional experience may substitute for formal education or certifications

Other Requirements

• Valid driver’s license and reliable vehicle
• Ability to pass a background check due to work with schools and municipalities
• Must reside in Wisconsin within approximately 20 miles of Darien, WI
• Relocation grace period may be considered
• Ability to travel regularly to client sites in Walworth County and surrounding areas

Compensation & Benefits

• Salary range: $75,000–$90,000 annually
• Medical, dental, and vision insurance
• Employer-matching 401(k)
• 15 days of PTO per calendar year, prorated during the first year
• Company-provided laptop
• Flexible work environment with a mix of remote and onsite work