IT Support Specialist - Intermediate

Are you an outgoing, client-focused technician who loves solving real-world problems and hates being chained to a remote helpdesk chair all day? Do you thrive in a close-knit, collaborative culture where your technical skills and personality both matter?

W don’t just close tickets! We deliver Absurdly Proactive Support. We act as the trusted technology department for small-to-midsize manufacturing and logistics firms across Eastern Massachusetts and Southern Rhode Island.

We are looking for an IT Support Specialist (Intermediate) who has the MSP scars (and triumphs) to prove they can walk into a client site, bring calm to chaos, and fix things right the first time., * Be the Trusted Face: Deliver white-glove, reassuring end-user support while maintaining a visible, friendly, and professional presence at client sites.

• Hands-On Triage & Resolution: Quickly diagnose and resolve hardware, software, network, and server issues with independence and confidence. You’re trusted to own problems, not just escalate them.
• Core Administration: Go beyond basic tier-1 helpdesk reset duties. You’ll actively administer Microsoft 365 environments, manage Windows workstations, and handle basic Windows Server roles.
• Own Your Notes & Escalations: Keep clients and our internal team aligned with crystal-clear communication, thorough documentation, and clean escalation notes.
• Drive Business Value: Help our manufacturing and logistics clients turn technology from a daily headache into a smooth, secure business advantage.

• Multi-Client IT Experience: At least 2+ years working in an MSP or fast-paced multi-client IT environment. You already know how to juggle multiple clients, work independently, and thrive under pressure.
• Technical Baseline: Solid, hands-on experience with Microsoft 365 Administration. Strong foundation in PC hardware, Windows OS troubleshooting, and basic Windows Server administration.
• Road-Ready & Independent: Valid driver’s license and reliable transportation. You’ll visit up to 3 client sites per week across Eastern MA and Southern Rhode Island. This isn’t a side gig. It’s core to the role, and we need someone dependable.
• Exceptional Communication: Clear, concise, and friendly verbal and written skills. You know how to stay calm and reassuring when dealing with stressed, non-technical users. You can explain technical concepts without the jargon.
• Culture Fit: You’re proactive, reliable, and genuinely interested in supporting your teammates and clients. You work hard, bring good energy, and actually enjoy what you do.
• Clear Background: Ability to successfully pass a background check.

Nice-to-Haves (Bonus points)

• Hands-on experience with Autotask, Datto RMM, or IT Glue.
• Familiarity with virtualization platforms (Proxmox is a plus).
• Experience with WatchGuard, Intermedia, or Keeper Security., * Active Directory: 2 years (Preferred)
• MSP: 2 years (Required)
• Mac OS: 1 year (Preferred)
• Windows: 5 years (Preferred)

License/Certification:

• MCP (Preferred)
• MCSA (Preferred)
• CCNA (Preferred)
• CompTIA Linux+ (Preferred)
• Driver’s License (Preferred)

Pulled from the full job description

• Travel reimbursement
• Professional development assistance
• Tuition reimbursement
• 401(k)
• Health insurance
• Retirement plan
• 401(k) matching, * Competitive Pay: $60,000 - $75,000 starting salary, scaled to match your hands-on experience and technical depth.
• Genuine Hybrid (14 Years Running): We’ve been hybrid since day one-not RTO-creep in disguise. You’ll split time between our Mansfield office, on-site client visits (averaging 2-3 days per week), and remote work. No surprise 100% office mandates. We mean it.
• Real Work-Life Balance & Stability: A true hybrid schedule with limited, compensated on-call for one of our top customers or monthly server patching. Outside of that, we work hard to respect your personal time. Plus a team that genuinely has your back and actually enjoys what we do.
• Robust Benefits Package: Health insurance assistance, PTO, 401(k) with match, profit sharing, phone expense allowance, tuition reimbursement, and travel reimbursement.
• Mentorship & No Dead Ends: Direct access to senior engineers and leadership who invest in your technical growth. No siloed helpdesks here-you get exposure to real network infrastructure, servers, and virtualization., * 401(k)
• 401(k) matching
• Health insurance
• Paid time off
• Professional development assistance
• Retirement plan