About this opportunity
Hometown Tech lists this Senior Support Technician opportunity in sharon, Wisconsin. Review the employer’s description below for duties, qualifications and application requirements.
Job description
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
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.