Senior Systems Engineer

We're SafePoint IT, a managed IT and cybersecurity provider based in the Chicago area. We run IT for small and mid-sized businesses, with a strong focus on healthcare practices (medical, dental and veterinary). Our clients are spread across several states, and so is our team. This is a fully remote role. Live where you want. A small town is fine. We care about the quality of your work, not your zip code. We also don't care how you learned it. If you taught yourself most of what you know and can prove it, you're who we're looking for. No certification checklist, no degree requirement. What you'll do You are a senior engineer on a small team. You take the tickets and projects nobody else can finish, you own them end to end, and you keep the client informed the whole way. Work escalated service tickets across desktops, servers, networks and cloud environments. Lead projects from design to handoff. Typical projects from our current work: Microsoft 365 tenant-to-tenant and email domain migrations. Entra ID risk policies, MFA enforcement, Conditional Access and security keys. Removing local admin rights and hardening endpoints through Intune. File server and business application migrations to SharePoint and the cloud. Server builds and retirements, and hosted desktop migrations. Firewall replacements, network upgrades and wireless rollouts. Password manager, cloud printing and AI assistant rollouts for business users. Security deployment and cleanup for new clients. Take part in technical scoping with our CTO and sales team before a project is quoted. Coach and back up our other engineers when they get stuck. Share a rotating on-call schedule. On-call weeks cover weekday evenings until 11:00 PM Central (midnight Eastern), plus weekends and federal holidays. Write clear notes. Every work session ends with an update to the client and a close-out note anyone on the team could pick up. What you bring 5+ years of hands-on IT experience. We don't care where you got it, as long as you can do the work above. MSP or multi-client consulting experience is a strong plus. 3+ years leading projects as the senior or lead technician. You learn new platforms on your own. Certifications and degrees are not required. Strong Microsoft 365, Entra ID (Azure AD), Intune, Exchange Online, SharePoint and Windows Server skills. Virtualization (Hyper-V or VMware), backup and disaster recovery. Firewalls, VPNs, switching and wireless. PowerShell or other scripting. Working knowledge of security frameworks such as NIST or CIS, plus MFA and Conditional Access. Plain-English communication, written and spoken. You'll take a short written test and a hands-on technical assessment. Nice to have Healthcare IT experience (HIPAA, practice management or imaging systems). Experience with endpoint detection and response, SOC escalations or incident response. How we measure the role Tickets worked to standard, with nothing unresolved left unescalated. Client satisfaction above 95%. Complete time entries and documentation, every time. Projects delivered on time and within scope. On-call shifts covered, with every call answered. Why join us $72,000 – $80,000 per year, based on experience. Medical through Blue Cross Blue Shield PPO plans, with the company paying half the premium, including dependents. Dental, vision, life and disability insurance. Retirement plan with company match. Paid time off and paid holidays. A defined career path: Senior Systems Engineer → Enterprise Engineer → vCIO. A small team where your work is seen, and a CTO who is hands-on. Fully remote, with company equipment shipped to you. This is a full-time, exempt role working Central Time business hours, reporting to the Service Manager. Remote setup: reliable high-speed internet, a quiet workspace suitable for client calls, and availability during Central Time business hours. All work is done on a SafePoint-issued, managed computer. You must be authorized to work in the United States without visa sponsorship, now or in the future. Any offer is contingent on a background check. We are an equal opportunity employer. Got a message from Alek about this role? Reply to him directly. You don't need to apply here first.