Fractional System Administrator

Pittsburgh, PA area (hybrid - some on-site required) | 1099 Contract | Flexible hours

We're an established telecom and technology consultancy in the Pittsburgh area, founded on 20+ years in the industry, and we're launching a managed services practice. We're already working with clients, and we need a senior technical mind on retainer - someone we can trust to plan and execute the work that can't go wrong.

What's on the table right now: Client migrations from incumbent MSP providers, infrastructure assessments, and security and compliance implementation work. A white-label help desk handles tier-1, so your hours go to the work that actually requires senior judgment.

What you'll do

• Plan and execute client cutovers from incumbent MSPs - firewall replacements, M365 tenant work, endpoint migrations, server assessments and decommissions
• Advise on system architecture, licensing, and tooling decisions before we commit clients to them
• Serve as our tier-2/3 escalation point above the help desk
• Review client environments during onboarding - tell us what's redundant, what's missing, and what's a liability
• Support security and compliance build-outs: MFA rollouts, endpoint monitoring, encryption, documentation
• Occasional on-site work in western PA for cutover nights and assessments

• 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. You'll occasionally be in front of clients, and how you treat people matters as much as what you know.
• The ability to speak in normal language to everyone from an office admin to a CEO. If you can only communicate in acronyms, this isn't your role.
• Deep hands-on experience with Microsoft 365 / Entra ID, Intune or comparable endpoint management, Windows Server, firewalls, and networking
• Reliability. When we schedule a cutover, you show up prepared.

Nice to have

Security/compliance framework experience (GLBA, HIPAA, CIS, NIST), RMM/PSA experience, low-voltage or hardware comfort., * IT: 3 years (Preferred)

Pulled from the full job description Flexible schedule, Monthly retainer plus hourly for project work, negotiable based on experience and availability. We're growing, and for the right person this engagement could grow with us - including the possibility of a full-time senior role as the practice scales., * Flexible schedule