Senior IT Support Specialist Jobs in Massachusetts

Davin Tech Group

Davin Tech Group is a managed IT and cybersecurity partner supporting mission-driven organizations across the country. We embed ourselves into our clients' operations, combining hands-on technical execution with thoughtful advice, clear communication, and high standards. We want people who take ownership, move with urgency, and care deeply about the people they support.

The Role

This is an experienced and senior role within our technical support team and a key escalation point for complex client issues. You'll work directly with our clients and alongside Specialists, Consultants, and Engineers to troubleshoot difficult problems, administer mission-critical systems, and keep client technology environments reliable, secure, and well supported.

You'll take ownership of more complex technical work, help guide and mentor other Specialists, improve documentation and support processes, and identify recurring issues that need a better long-term solution. We expect you to bring strong technical judgment, communicate clearly under pressure, and operate with a high degree of independence while knowing when to involve a Consultant or Engineer.

What You’ll Do:

• Own complex client support requests from first contact through resolution and follow-up.
• Troubleshoot advanced issues across users, endpoints, SaaS, identity, networks, servers, security, and infrastructure.
• Administer Microsoft 365, Google Workspace, Active Directory/Entra ID, endpoint management, and identity platforms.
• Serve as a technical escalation point and partner with Consultants and Engineers on high-impact issues.
• Own technical onboarding and offboarding, including devices, identities, applications, and access.
• Support networks, firewalls, wireless, conference rooms, and office technology.
• Manage technology procurement, deployment, inventory, and lifecycle.
• Mentor Associate IT Specialists and IT Specialists through troubleshooting and knowledge sharing.
• Lead technical work for migrations, deployments, refreshes, office buildouts, and security initiatives.
• Identify root causes and drive improvements to systems, monitoring, standards, and workflows.
• Improve documentation, procedures, and technical standards across client environments.
• Stay engaged during critical incidents and help drive issues to durable resolution.

Who We’re Looking For:

You’re an experienced, high-agency problem solver who is energized by difficult challenges and comfortable operating in unfamiliar territory. You don’t need to have every answer immediately, but you know how to research deeply, troubleshoot methodically, test assumptions, and work a problem until you understand what’s really happening. You also have the technical judgment to recognize when to keep digging, when to bring in another Specialist, and when a Consultant or Engineer needs to be involved.

You enjoy the variety that comes with supporting different clients, industries, environments, and technologies, and you can manage competing priorities without losing sight of the details. You notice patterns, edge cases, configuration problems, security concerns, and recurring issues, and you look beyond the immediate fix to identify what should be improved so the problem doesn’t keep coming back.

You’re a people-first technologist and an exceptional communicator. You can take control of a stressful client situation, ask precise questions, explain complex issues clearly, and keep clients and internal teams informed even when the answer isn’t simple. You’re comfortable being the person others turn to when an issue is difficult, ambiguous, or high-impact.

Just as importantly, you raise the bar for the people around you. You share what you know, mentor other Specialists, improve documentation and support processes, and help teammates develop stronger troubleshooting habits and technical judgment. You operate with a high degree of independence while understanding that great technical leadership also means knowing when to collaborate.

You set the standard for how great technical support is delivered at Davin.

What You Bring:

• 5+ years of hands-on IT support or systems administration experience, ideally in an MSP or client-facing environment.
• Advanced troubleshooting across Windows, macOS, mobile devices, cloud applications, identity, endpoints, networking, and infrastructure.
• Strong experience with Microsoft 365, Google Workspace, Box, Dropbox, Monday, Slack, Teams, Zoom, VOIP, and other industry-specific line of business applications.
• Strong experience with Active Directory, Entra ID, and other identity and access management platforms.
• Working knowledge of firewalls, wireless, VPNs, servers, backup, and core infrastructure.
• A practical understanding of cybersecurity fundamentals across endpoint, identity, and access controls.
• Excellent written and verbal communication with clients and technical teams.
• Strong judgment, organization, and the ability to work independently under pressure.
• A track record of mentoring teammates and improving processes, documentation, and systems.

Bonus points:

• Deep experience in a fast-paced managed services environment.
• Deep experience supporting executives, founders, or other high-touch users.
• Experience with RMM/MDM, EDR, SSO/MFA, backup, firewalls, switching, and wireless.
• PowerShell, scripting, automation, or other experience eliminating repetitive work.
• Exposure to HIPAA, SOC, CMMC, or other regulated environments.
• Experience supporting executives, leading incident response, or delivering complex migrations.

Physical & Work Environment:

This is a hands-on role, and sometimes that means getting away from the desk. You may be installing equipment, tracing cabling, moving between workstations, or working in network and IT spaces. With or without reasonable accommodation, you should be able to lift and move equipment up to 50 pounds, crouch or kneel when needed, and use a computer and standard office equipment for extended periods.

Location & On-site Expectations:

This role is based at our headquarters in Plymouth, MA, with hybrid flexibility and regular client-site work. Our clients span nationwide, so you should be comfortable getting on the road when the work calls for it.

Reliable transportation and the ability to travel to local client locations are required. Davin provides commuter benefits and mileage reimbursement in accordance with IRS guidelines.

Compensation & Benefits:

$85,000 - $95,000 per year, depending on experience, plus monthly incentive pay program.

• Health, dental, and vision insurance (100% covered for employees; 50% for dependents).
• Company-paid short-term disability, long-term disability, and life insurance.
• 401(k) with company match.
• Unlimited PTO.
• Flexible work environment.

How We Work:

• Take ownership. Do what you say you'll do. If something changes, communicate.
• Move with urgency. Not everything is an emergency, but important things don't sit around.
• Figure things out. Investigate, ask good questions, involve the right people, and keep moving.
• Take care of people. The person on the other side of the technology matters.
• Leave it better. Solve today's problem and look for ways to prevent tomorrow's.

How to Apply:

Send your resume and a brief introduction to careers"@"davintechgroup.com. Tell us why you're interested in the role, what makes you a strong fit, and anything you've built, learned, or worked on that we should know about.

Note: We will review and consider all applicants.

Pay: $85,000.00 - $95,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Parental leave
• Professional development assistance
• Referral program
• Retirement plan
• Vision insurance

Work Location: Hybrid remote in Plymouth, MA 02360