Cheshire, Connecticut, United States On-site Employment

HAI Group is hiring a Senior Support Desk Engineer

About the Role

HAI Group is looking for a Senior Support Desk Engineer to serve as the critical escalation point for complex technical issues within our support team. You will leverage deep product and systems knowledge to resolve advanced customer problems and partner with technical teams to improve our platforms.

What You'll Do

  • Provide advanced technical support for software, hardware, and network-related issues escalated from initial support.
  • Perform asset tracking and inventory management for all IT assets, including hardware, software, and contracts.
  • Diagnose, troubleshoot, and resolve complex customer problems via phone, email, chat, or remote access tools.
  • Ensure all support activities and resolutions are thoroughly documented within the ticketing system.
  • Work in partnership with Infrastructure and Application Development teams to resolve and escalate product bugs or systemic issues.
  • Manage and execute deployment requests.
  • Create and update technical documentation, knowledge base articles, and FAQs.
  • Offer technical instruction and support to Service Desk team members.
  • Participate in root cause analysis and provide feedback for product and process improvements.
  • Ensure timely follow-up and communication with customers regarding issue status.
  • Keep up to date with IT products, services, and trends to ensure platforms remain modern.
  • Collaborate closely with operations engineers during escalations involving complex, non-routine, or systemic issues.

What We're Looking For

  • Bachelor’s degree in computer science, Information Technology, or related field (or equivalent experience).
  • 5+ years of experience in a technical support or IT helpdesk role.
  • Strong analytical and problem-solving skills with attention to detail.
  • Proficiency with System Software (Windows and IOS), networking protocols, and application software.
  • Excellent verbal and written communication skills.
  • Ability to work independently and within a team environment.
  • Customer-focused attitude and ability to manage challenging situations professionally.
  • Ability to handle multiple tasks and prioritize effectively under pressure.
  • Strong desire for continuous learning and professional development.

Nice to Have

  • Experience with ticketing systems and remote support tools; Jira experience is a plus.
  • Technical certifications (e.g., CompTIA, Microsoft).
  • Experience supporting enterprise-level clients or mission-critical environments.
  • Knowledge of cloud technologies, virtualization, and cybersecurity concepts.

Technical Stack

  • Windows, IOS, M365, SharePoint, Copilot

Team & Environment

Works closely with support staff, development teams, and other technical specialists. Part of the Information Technology department.

Benefits & Compensation

  • Bonus program eligibility
  • Annual merit program
  • Outstanding 401(k) program and non-elective contribution
  • Flexible work schedules
  • Generous paid time off, paid volunteer days and paid holidays
  • Medical, vision and dental Insurance
  • Company paid life, AD&D, short-term disability, and long-term disability coverage
  • HSA, FSA and dependent care options
  • On-Site wellness: Full gym and locker rooms, wellness initiatives, outdoor basketball and tennis court, picnic pavilion area
  • Tuition reimbursement and loan repayment
  • Professional development
  • Community outreach

Work Mode

This is an on-site position located in Cheshire, Connecticut.

HAI Group is an Equal Opportunity Employer.

Required Skills
WindowsIOSM365SharePointCopilotTechnical SupportIT HelpdeskNetworking ProtocolsSystem SoftwareProblem-Solving
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About company
HAI Group

HAI Group is the nation’s leading property-casualty insurance company founded by and dedicated to affordable housing organizations. Besides insurance, we offer risk management services, online training, and consulting services used by more than 1,500 housing organizations nationwide.

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Job Details
Department Information Technology
Category other
Posted 14 days ago