IT Systems Support Specialist

Cobalt Benefits Group is seeking an IT Systems Support Specialist to support our network, cloud, and end-user environment. This is an ideal opportunity for a seasoned Helpdesk or Service Desk professional with 3–5 years of experience and ready to expand into 

infrastructure, networking, and cloud operations.

What You’ll Do

Network & Infrastructure Support

• Troubleshoot connectivity issues across devices, platforms, and applications 

• Support hybrid infrastructure (on-prem cloud environments) 

• Assist with ZTNA, secure access, and remote connectivity solutions

• Help maintain network documentation and system configurations

T Service Desk (Zendesk)

• Manage and resolve user tickets in Zendesk (SLA-driven)

• Troubleshoot endpoint, application, and access-related issues

• Perform onboarding/offboarding (account provisioning, access assignments)

• Escalate and collaborate with Infrastructure and Security teams

• Identify recurring issues and contribute to operational improvements

Systems, Identity & Secure Access (Growth Area)

• Support Microsoft 365 (Exchange, Teams, SharePoint)

• Assist with Microsoft Intune endpoint management

• Support identity and access tasks within Entra ID

• Assist with role-based and group-based access controls (least privilege concepts) 

• Gain exposure to secure access architecture and Zero Trust principles

Operational & Engineering Support

• Assist with infrastructure deployments and configuration tasks 

• Participate in troubleshooting, monitoring, and system optimization 

• Contribute to system documentation and process improvements 

• Support change management and rollout activities for new technologies 

What We’re Looking For

Required

• 3–5 years of IT experience (Helpdesk, Service Desk, or Junior Administrator)

• Hands-on experience with a ticketing system (Zendesk strongly preferred)

• Solid troubleshooting and issue resolution skills

• Basic networking knowledge (TCP/IP, DNS, DHCP, VPN)

• Experience supporting Windows endpoints and users

• Strong communication and customer service mindset

Core Technical Skills

• Microsoft 365 administration (basic to intermediate)

• Endpoint support and lifecycle management (Intune exposure a plus)

• Hybrid infrastructure familiarity (cloud on-prem) 

• Identity and access fundamentals (Entra ID / Azure AD exposure) 

• System troubleshooting and performance monitoring

Nice to Have

• Exposure to Zero Trust or secure access concepts

• Familiarity with enterprise applications and access management 

• Basic PowerShell or scripting

• Experience working in regulated environments

Growth Path

This role is designed as a feeder into:

• Systems Administrator (Cloud / Azure)

• Network Administrator / Engineer

• Identity & Access / Security Engineering

Why Join Us

• Direct exposure to modern enterprise stack (Azure, Entra ID, Intune)

• Hands-on experience with security-driven infrastructure (Zero Trust initiatives)

• Opportunity to grow beyond Helpdesk into Engineering

• Strong mentorship from senior infrastructure and security team

Benefits:

After successfully completing a waiting period, eligible Full-time employees have access to our comprehensive benefits package, including:

• Fantastic medical, dental, and vision insurance*
• Twice annual employer HSA contributions, covering 50% of the HDHP plan’s annual deductible!
• Company provided Basic Life and AD&D
• Company paid Short-Term and Long-Term Disability**
• Flexible Spending Accounts*
• 401(k) Retirement Plan with up to a 6% employer-match** WOW! (100% fully vested after 3 years)
• 10 paid holidays
• Generous paid vacation and sick time
• Annual Volunteer Paid Day
• Annual Tuition Reimbursement
• Annual Health and Wellness Reimbursement
• Lots of fun company events

*60 day waiting period

**90 day waiting period

Who We are:

As a trusted third-party administrator (TPA) specializing in self-funded benefit plans, Cobalt Benefits Group (CBG) is committed to helping employers find high-quality coverage at a cost they can afford. We administer self-funded insurance benefits through our three companies: EBPA, Blue Benefit Administrators of Massachusetts, and CBA Blue.

With over 30 years of experience and a dedicated team of more than 200 employees, we work collaboratively to build customized self-funded health plans, manage claim payments and disputes, and administer other specialized programs such as FSAs, HSAs, COBRA, and retiree billing. Join us as we match employers across our region with the right solutions for their employee benefit needs. To learn more about working at CBG, visit https://www.cobaltbenefitsgroup.com/careers/.

Cobalt Benefits Group is an Equal Employment Opportunity Employer 

Cobalt Benefits Group participates in E-Verify to confirm the employment eligibility of all new hires.