Systems Support Specialist Helpdesk Position Available In Chittenden, Vermont

Systems Support Specialist- Helpdesk 2.6 2.6 out of 5 stars South Burlington, VT 05403

Description:

Join our team at Cobalt Benefits Group and start an exciting new career in employee benefits solutions. As a Systems Support Specialist- Helpdesk , you’ll play an important role in helping us offer customized, self-funded insurance options to our clients and members. In this role, you’ll go beyond traditional helpdesk duties, acting as the go-to person for a wide range of technology needs—from user support and systems troubleshooting to network management and basic infrastructure maintenance. This is a great opportunity for someone who enjoys variety, problem-solving, and working directly with end-users and leadership in a fast-paced, hands-on environment.

Key Responsibilities:

Respond to technical support inquiries via phone, email, or ticketing system in a timely and professional manner. Serve as the primary point of contact for day-to-day IT support across hardware, software, and network issues. Troubleshoot and resolve desktop, laptop, mobile device, printer, and peripheral issues across Windows and macOS environments. Set up and manage user accounts, permissions, and access using tools like Active Directory and Microsoft 365 Admin. Collaborate with other team members to share knowledge and best practices, contributing to a culture of continuous improvement. Assist in IT infrastructure tasks such as backup monitoring, device imaging, system patching, and light scripting (e.g., PowerShell). Manage the procurement, inventory, and lifecycle of IT equipment. Document IT procedures, system configurations, and known issues for internal reference. Collaborate with vendors and third-party service providers for specialized support. Provide after-hours support on a rotation or during critical outages and maintenance.

Requirements:

3+ years of hands-on IT support experience. Strong troubleshooting skills across hardware, OS (Windows/macOS), and common productivity platforms (Microsoft 365, Google Workspace, etc.). Working knowledge of networking fundamentals (IP, DNS, DHCP, VLANs). Proven experience in a technical support role, preferably in a helpdesk or customer support environment. Ability to multitask, prioritize, and self-manage in a lightly structured environment. Excellent interpersonal and communication skills—must be comfortable interacting with non-technical users.

Personal Attributes:

Experience Supporting hybrid IT environments. Familiarity with endpoint management tools (e.g., Intune, jamf, PDQ) Light experience with scripting or automation (PowerShell, Bash, etc.). CompTIA A+, Network+, or equivalent certifications a plus. Work Environment & Physical Demands Prolonged periods of sitting may be required. Regular use of a computer, keyboard, and mouse is necessary; reasonable accommodations will be provided upon request. Employees should ensure an ergonomically appropriate desk and chair setup. Comfort with being on camera for virtual meetings (e.g., Microsoft Teams)

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 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/.

Benefit Waiting Period Notes:

60 day waiting period

• 90 day waiting period Equal Opportunity Employer, including disability/protected veterans PI273757240