Job Summary
Systems Administrator — Founding Technical Hire at a Growing MSP
Pittsburgh, PA area (hybrid) | Full-Time
Most sysadmin jobs put you in a queue closing tickets for a company. This isn't that.
We're a new managed service provider founded by people with 20+ years in the telecom and technology industry. We're already working with clients, we will have a full vendor stack and a white-label help desk handling tier-1 so you don't have to, and we're growing deliberately. What we don't have yet is our senior technical hire. That's this role — you'd be the technical foundation of this company, and we need someone who can hit the ground running.
What’s on the table right now: Active client migrations from incumbent providers, including a significant security and compliance build-out — written security program, MFA rollout, endpoint monitoring, encryption, incident response planning.
What you’ll do
- Serve as our lead technical resource — you own the engineering side of every client environment
- Plan and execute client migrations and cutovers from incumbent MSPs: environment assessments, M365 tenant work, firewall replacements, endpoint migrations
- Lead security and compliance implementations — if you’ve built a security program under any framework (CIS, NIST, GLBA, HIPAA), you can do this
- Act as tier-2/3 escalation above our help desk, and design the escalation and documentation standards yourself
- Advise ownership on architecture, licensing, and tooling — your technical judgment shapes what we recommend to clients
- Be client-facing. Regularly. Including sitting in planning meetings with VPs and owners.
What we require — non-negotiable
- 3+ years at an MSP or in a similar multi-client environment. You’ve lived through cutover nights and know what a clean handoff from an incumbent looks like.
- Exceptional customer service skills. We will not waver on this. Technical skills matter, but how you treat people is who you are. Our clients need to feel taken care of every single time.
- The ability to speak in normal language to everyone from an office admin to a CEO. You’ll be in rooms with IT Directors, VPs, CIOs, CTOs, and business owners. If you can only communicate in acronyms, this isn’t your role. If you can make a CEO feel confident and an end user feel heard — keep reading.
- Strong hands-on skills in Microsoft 365 / Entra ID, Intune or comparable endpoint management, Windows Server, firewalls, and networking
- Sound independent judgment — you’ll often be the most technical person in the room, and we need to trust what you tell us
- Reliability and follow-through.
Nice to have
Security/compliance framework experience (GLBA, HIPAA, CIS, NIST), RMM/PSA experience, low-voltage or hardware comfort.
What we offer
Competitive salary based on experience, real ownership of the technical function from day one, a say in every tooling and process decision, and room to grow into leadership roles — and maybe more — as the business grows. Within the year, you’ll likely be building and leading a team under you. No bureaucracy, and no ticket-mill burnout.
To apply
Send a resume and a short note answering one question: tell us about a time you turned a frustrated customer into a happy one. That answer matters more to us than your certifications.
Pay: $55,000.00 - $75,000.00 per year
Benefits:
- Flexible schedule
- Paid time off
- Professional development assistance
Experience:
Work Location: Hybrid remote in Pittsburgh, PA 15202
