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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Help Desk Technician - **Company:** Reserve Group Management Company - **Location:** Chicago, IL, United States - **Salary:** $53,040.0 - $59,280.0 - **Contract:** Permanent contract - **Skills:** Microsoft Windows, Active Directory, Business Software, Microsoft Outlook, Distributed Systems, Issue Tracking Systems, Virtual Private Networks (VPN), Networking Basics, Windows PowerShell, Microsoft SharePoint, User Provisioning Software, Virtual Local Area Networks, Wi-Fi Technology, Scripting, Peripherals, Microsoft InTune, Laptops, User Accounts - **Published:** June 29, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=736f6910bef1b556 ## About the Role Do you have experience in Windows?, * 1+ years of help desk or desktop support experience (or equivalent training/certifications) * Solid working knowledge of Windows operating systems and Microsoft 365 * Familiarity with Active Directory user and group administration * Comfort troubleshooting hardware, printers, and basic networking * Experience working from a ticketing/queue and documenting your work clearly * Strong customer service skills and the patience to support non-technical users * Proven ability to follow written and verbal instructions, established procedures, and company policies accurately and consistently * A disciplined, detail-oriented approach to doing things the right way, even when no one is watching * Ability to prioritize, follow through, and communicate status proactively * Reliable, self-directed, and comfortable in a hands-on industrial setting * Willing and able to travel to Ohio (paid) for training and periodic in-person team collaboration throughout the year Nice to Have * Exposure to Intune / endpoint management * Basic networking knowledge (switching, VLANs, Wi-Fi) or vendor familiarity (Aruba, UniFi, Palo Alto) * Any scripting (PowerShell) or automation experience * Relevant certifications (CompTIA A+/Network+, Microsoft fundamentals) * Prior experience supporting multi-site or distributed environments ## Description As an IT Help Desk Technician, you'll be physically based at our Chicago facility, but you'll work as a fully integrated member of our Ohio-based IT team. While you'll have a presence on the ground in Chicago, you are not a one-person, siloed operation, you'll collaborate daily with the broader IT team in Ohio, follow shared processes and standards, and have direct support and mentorship from senior staff. This is the best of both worlds: hands-on, in-person work locally, backed by a connected team behind you. This position reports directly to the CTO of IT, based in Ohio. Paid travel to Ohio is required for initial training and several times throughout the year to work directly with the team in person. You'll be the first point of contact for technical support across our organization, helping roughly 170 users stay productive day to day. You'll resolve issues spanning hardware, software, accounts, and connectivity, and you'll partner with our networking, infrastructure, and systems teams on anything that needs to be escalated. This is a hands-on role in a real industrial environment, ideal for someone who likes solving problems and wants room to grow into deeper IT work. What You'll Do * Serve as the first line of support for end users, handling requests by ticket, phone, and in person * Triage, document, and resolve incidents and service requests using our ticketing system, escalating to senior IT staff when needed * Work closely with the Ohio-based IT team, following shared standards, processes, and documentation so support is consistent across every site * Follow established IT policies, procedures, and instructions precisely, and complete tasks the way they're documented and directed * Set up, image, and deploy desktops, laptops, mobile devices, and peripherals * Manage user accounts, group membership, and access in Active Directory and Microsoft 365 / Entra * Support employee onboarding and offboarding, including provisioning and deprovisioning hardware and accounts * Troubleshoot Windows, Microsoft 365 (Outlook, Teams, OneDrive, SharePoint), printers, and common business applications * Provide basic network and connectivity troubleshooting (wired, wireless, VPN) and coordinate with the networking team on larger issues * Maintain accurate inventory and asset records, and keep documentation current * Travel to Ohio (paid) for initial training and several times per year to collaborate directly with the IT team, plus occasional travel to nearby RMG facilities as needed ## Related Videos - [Develop enterprise-ready applications for Microsoft Teams with Azure resources on modern web technologies](https://www.wearedevelopers.com/videos/187-develop-enterprise-ready-applications-for-microsoft-teams-with-azure-resources-on-modern-web-technologies) - [Agentic employees in world's most downloaded FinTech app](https://www.wearedevelopers.com/videos/100123-agentic-employees-in-world-s-most-downloaded-fintech-app) - [Building a Cross-Platform BLE Client with Kotlin Multiplatform and Kable](https://www.wearedevelopers.com/videos/100250-building-a-cross-platform-ble-client-with-kotlin-multiplatform-and-kable) - [JavaScript? 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