Senior Support Technician
Hometown Tech · Sharon, WI
Apply & track with Apply EdgeRole Title: Senior Support Tech
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 issuesServe as a primary escalation point for Support Techs and Advanced Support TechsTake ownership of difficult technical issues and drive them through diagnosis, resolution, documentation, and follow-upPerform root-cause analysis and identify long-term solutions rather than relying solely on temporary fixes or workaroundsIdentify recurring technical problems, inefficiencies, and risks and recommend changes that improve client environmentsAdminister and troubleshoot Microsoft cloud and domain-based environments, including Microsoft 365, Microsoft Entra ID, on-prem Active Directory, and hybrid deploymentsTroubleshoot complex authentication, access control, synchronization, DNS, DHCP, Group Policy, device compliance, identity, and cloud service issuesConfigure, administer, and troubleshoot Microsoft Intune and other endpoint management systemsSupport and troubleshoot Windows servers and related infrastructureAdminister and troubleshoot Google Workspace environmentsTroubleshoot and support network infrastructure involving firewalls, gateways, switches, VLANs, VPNs, routing, DNS, Wi-Fi, and related technologiesIndependently install and deploy workstations, servers, networking equipment, cloud services, and other client systems according to approved specifications and implementation plansExecute system migrations, infrastructure upgrades, equipment replacements, and new system deploymentsValidate completed installations and deployments to ensure systems operate according to specificationsTroubleshoot interactions between multiple systems, vendors, applications, and infrastructure componentsProvide technical guidance, mentoring, and troubleshooting assistance to Support Techs and Advanced Support TechsAssist other technicians in developing troubleshooting approaches that address root causes rather than symptomsParticipate in project implementations under the direction of the System ArchitectIdentify situations requiring architectural, security, or design decisions and escalate those decisions to the System Architect when appropriateCommunicate directly with clients regarding complex technical problems, recommendations, implementation activities, and resolution statusCreate and maintain accurate technical documentation, implementation notes, procedures, and client environment informationFollow Hometown Tech standards, security requirements, documentation practices, and implementation proceduresTravel regularly to client sites in Walworth County and surrounding areasParticipate in an on-call rotation as needed to support client needsKnowledge & SkillsExpert troubleshooting and analytical problem-solving skillsBroad understanding of IT infrastructure, systems administration, networking, cloud services, endpoint management, and end-user computingStrong working knowledge of Microsoft 365 and Microsoft Entra IDStrong working knowledge of Active Directory, Group Policy, DNS, DHCP, authentication, permissions, and hybrid Microsoft environmentsStrong experience with Microsoft Intune and modern endpoint managementStrong understanding of networking concepts including firewalls, routing, switching, VLANs, VPNs, DNS, DHCP, and Wi-FiExperience supporting Windows server environments and common server infrastructureWorking knowledge of Google Workspace administrationAbility to troubleshoot unfamiliar technologies using documentation, logs, testing, research, and systematic analysisAbility to identify the underlying cause of a problem rather than addressing only its immediate symptomsAbility to evaluate whether an existing solution is sustainable and recommend a more reliable long-term approach when appropriateAbility to independently execute technical installations and deployments from specifications, documentation, and implementation plansAbility to recognize when a technical issue requires an architectural or security decision outside the scope of an established implementationAbility to prioritize and manage multiple complex technical issues independentlyAbility to clearly communicate complex technical concepts to both technical and non-technical usersStrong documentation, organizational, and attention-to-detail skillsStrong initiative, accountability, professional judgment, and willingness to continue learning new technologiesExperience & EducationMinimum of 8 years of professional IT support, systems administration, infrastructure, managed services, or comparable technical experienceSignificant experience independently troubleshooting complex technical issuesExperience supporting Microsoft 365, Microsoft Entra ID, Active Directory, and hybrid Microsoft environmentsExperience implementing and supporting business networks, endpoint management systems, servers, and cloud servicesExperience performing system deployments, migrations, upgrades, or infrastructure installationsManaged services or multi-client IT experience strongly preferredRelevant Microsoft, networking, security, or other industry certifications are preferred but not requiredEquivalent professional experience may substitute for formal education or certificationsOther RequirementsValid driver’s license and reliable vehicleAbility to pass a background check due to work with schools and municipalitiesMust reside in Wisconsin within approximately 20 miles of Darien, WIRelocation grace period may be consideredAbility to travel regularly to client sites in Walworth County and surrounding areasCompensation & BenefitsSalary range: $75,000–$90,000 annuallyMedical, dental, and vision insuranceEmployer-matching 401(k)15 days of PTO per calendar year, prorated during the first yearCompany-provided laptopFlexible work environment with a mix of remote and onsite work