Regional IT Support Specialist

CFS; Enfield (CT); On-site; USD 55,000 - 65,000; Full time

Benefits offered by this job

Overtime opportunities

Mileage reimbursement

Healthcare benefits

Job summary

CFS is seeking a Regional IT Support Specialist to provide hands-on IT support across Southern Connecticut, spanning New Haven to Stamford. You will work across multiple sites, supporting Windows environments, Microsoft 365, cloud technologies, and hardware deployments.

The ideal candidate has 1-3 years of IT support experience, enjoys problem solving, and prefers field work to sitting at a desk. The role offers a $55,000-$65,000 salary plus overtime and mileage reimbursement.

Qualifications

• 1-3 years of IT support or field services experience.
• Solid troubleshooting and problem-solving skills.
• Familiarity with Windows environments and Microsoft 365.

Responsibilities

• Provide hands-on IT support across multiple locations in Southern Connecticut.
• Travel between sites to resolve hardware, software, connectivity, and end-user issues.
• Support Windows, Microsoft 365, user administration, and endpoint technologies.

Skills

IT Support

Windows Environments

Microsoft 365

Customer Service

Travel to sites

Tools

Active Directory

Intune

Networking Basics

Job description

Regional IT Support Specialist

Southern Connecticut Territory (New Haven – Stamford)

$55,000 - $65,000 + Overtime + Mileage Reimbursement

Looking for More Than a Help Desk Job?

A growing, multi-site environmental and industrial services organization is seeking a hands‑on IT professional to support operations throughout Southern Connecticut.

This is an ideal opportunity for someone with 1‑3 years of IT support experience who wants more than password resets and ticket queues. You’ll become the primary technology resource for a defined territory, supporting employees across multiple locations while gaining exposure to infrastructure, networking, Microsoft 365, cloud technologies, hardware deployments, and technology modernization initiatives.

If you’re the type of person who enjoys solving problems, learning new systems, and spending time in the field instead of sitting behind a desk all day, we’d love to hear from you.

Why Consider This Opportunity?

• Become the go‑to IT resource for an important and growing territory
• Enjoy a highly visible role with real ownership and autonomy
• Gain exposure to infrastructure, networking, cloud technologies, security initiatives, and large‑scale IT projects
• Work with a collaborative team while maintaining significant independence in your day‑to‑day responsibilities
• Support a diverse mix of office, operational, and industrial environments
• Consistent overtime opportunities that can increase annual earnings
• Strong benefits package including healthcare, retirement benefits, paid time off, and mileage reimbursement
• Clear career growth opportunities into Systems Administration, Infrastructure, and Engineering roles

What You’ll Be Doing

• Provide hands‑on IT support across multiple locations throughout Southern Connecticut
• Travel between sites resolving hardware, software, connectivity, and end‑user issues
• Serve as the primary IT presence within your assigned territory
• Support Windows environments, Microsoft 365, user administration, and endpoint technologies
• Configure and deploy laptops, desktops, mobile devices, and peripherals
• Troubleshoot network connectivity and support cloud‑managed technologies
• Assist with system upgrades, refresh projects, and technology rollouts
• Build strong relationships with users and become a trusted technology resource
• Collaborate closely with a centralized IT team while managing field priorities independently

What Makes Someone Successful Here?

• You enjoy variety and don’t want to be tied to one desk or office
• You take ownership of issues and see them through to resolution
• You’re comfortable working independently and managing your own schedule
• You enjoy helping people and building relationships with end users
• You’re naturally curious and enjoy learning new technologies
• You want a long‑term career path with opportunities to grow

Qualifications

• 1‑3+ years of IT Support, Desktop Support, Field Services, or Technical Support experience
• Strong experience supporting Windows environments
• Familiarity with Microsoft 365 technologies
• Excellent troubleshooting and problem‑solving skills
• Strong customer service and communication abilities
• Valid driver’s license and willingness to travel throughout Southern Connecticut
• Ability to work independently and prioritize competing demands

Preferred Experience

• Active Directory or Microsoft Entra ID
• Intune or endpoint management platforms
• Basic networking troubleshooting
• Device deployment and imaging
• Cloud technology exposure
• Experience supporting multiple sites or field locations