IT Support Technician - Microsoft 365, AD & Migration Support

Proactive Technology Management · Royal Oak, MI · Remote

Posted 7/7/2026 · last confirmed live 8/26/2026

Apply on Proactive Technology Management’s site

Proactive Technology Management is looking for an experienced IT professional in the Oakland County area to join our team. We're looking for a motivated, independent IT expert who feels confident communicating with a remote team of talented techs. If you like working in different client environments providing excellent customer service and technical support, this role could be for you! The ideal candidate has broad IT knowledge and high accountability that keeps them driven towards success and personal growth. We offer a fairly defined, upward path with money and responsibility. Location: We are looking for someone to work full time in the Oakland County area. Proactive Technology Is Different: Monthly check-ins and annual path planning Defined path for career development and personal growth Fun, team-based approach Constantly learning new tech We are Nuts about IT The Path: Technician -> Integrator -> Engineer -> Consultant Along the way, you may work remotely or on site with clients. Initially, you will not be assigned clients. As you grow into a senior technician role, you will have the opportunity to be assigned to and work directly with specific clients. This makes you a Primary. Moving along this path will put you in charge of larger clients, requiring more extensive knowledge of technology to help support our clients. Some techs may branch off along the way and become specialists in a specific area of IT like security, networking, or cloud. Our Primaries are in charge of their clients from keyboard to cloud. They work with the decision makers to guide purchasing decisions, setup new equipment, and implement new services. This person must love helping people with technology and excellent communications skills are essential. The Position: We are hiring an experienced technician entering at the Integrator level. This person would work a hybrid schedule, with most troubleshooting being handled remotely with on-site visits as needed. 4+ years working at or above Tier 3-level support or in a specialist role is preferred. Primary technicians work directly with our clients and other IT professionals - if you enjoy interfacing with multiple people on a daily basis and problem solving on the go, this role could be a great fit for you! What to expect in your first 30 days: Week 1 - Shadow and Learn This is your initial introduction to our team, processes, and accounts. We make sure you understand our systems and how we use them, and help you acclimate to our company structure and what your daily schedule layout looks like. This week is a lot of shadowing and sitting in on larger projects and joining our call queue. You will start tracking your time on a regular basis in our ticketing system (ConnectWise Manage). Week 2 - Shadow and Start Doing After your initial introduction to the team, your shadowing will transition to more of an active role in troubleshooting and on-site projects. Your schedule could include handling a few remote troubleshooting tickets or calls and joining another tech for an on-site for the second half of the day. Ideally our new employees will have first-hand experience in client interactions, on-site projects, and remote troubleshooting by the end of Week 2. Week 3 and Week 4 - Do and Observe Approaching your first 30 days with Proactive, you should feel confident jumping in the call queue, taking tickets and hand-offs from other team members, joining techs for on-site visits, and tracking all of your time consistently. You will have a 30-day check-in to ensure you feel confident doing the above, tracking your hours, and have a solid understanding of what your job expectations are on your team. Requirements This is a fast-paced and dynamic position requiring a strong grasp of the fundamentals of Networking, Office 365, Windows Desktops, Windows Servers, Active Directory, and Security . Troubleshooting, implementation, and installation are of the key areas of knowledge to be successful in this position. Must Have: 5+ Office 365 and Windows Server experience 5+ Firewall troubleshooting experience (Sophos, Cisco, SonicWall, Watchguard) 5+ Network Setup experience (installing AP's, switches, and firewalls ) Extensive experience leading migrations Extensive experience in virtualization and networking Above and beyond customer service Good To Have: Bachelor's degree IT-related certifications MSP Experience Responsibilities: Setting Up Customer Networks (cloud to keyboard) Windows Server Installation Configuration Maintenance Ongoing Support (access points, firewalls, and switches) Remote troubleshooting of client, as well as on-site when required Monday - Friday schedule One Saturday per month for the first 18 months Benefits Full Medical Benefits 2 Weeks Paid Vacation Full Time Dental & vision insurance 401(k) matching

This role is published by Proactive Technology Management on workable. SwiftFit is not the employer and does not accept applications.