Senior IT Helpdesk Specialist

Senior IT Helpdesk Specialist (Full-Time)
HR & Recruiting Firm

Location:

Mostly In-person in Milford, CT, very Occasional Travel

• Act as the main contact for IT support requests via phone, email, or ticketing system.
• Troubleshoot and resolve hardware, software, and connectivity issues for remote and onsite users.
• Provide high-priority, professional support to leadership and executives, ensuring minimal downtime.
• Escalate complex technical issues to senior IT management or external vendors when appropriate.

• Manage and support Microsoft 365
  , Teams, and user account administration.
• Lead new employee onboarding, including account creation, device setup, and access management.
• Develop and refine onboarding documentation and checklists to streamline the process.
• Gain experience and expand skills in Microsoft Entra (Azure AD),
  Intune
  , and mobile device management (MDM) systems.

• Create and maintain IT documentation, internal knowledge bases, and standard operating procedures.
• Identify recurring issues and develop long-term solutions to improve system reliability.
• Suggest and collaborate ideas for new tools, systems, and workflow improvements.

• Perform regular system updates, monitoring, and backups.
• Manage user access controls and maintain compliance with IT policies.
• (Bonus) Contribute to cybersecurity and endpoint protection initiatives.

• Support IT setup and system configuration for new office or client locations (occasional travel).
• Assist in technology rollouts and adoption of new solutions.

Required:

• 3+ years of IT support or helpdesk experience.
• Proficiency with Microsoft 365
  , Windows OS, and general networking fundamentals.
• Excellent troubleshooting and communication skills, including experience supporting leadership and executive-level users
  .
• Strong documentation and process improvement abilities.
• Ability to work collaboratively in a remote, fast-paced environment.

Preferred:

• Experience working in startup or rapidly growing business environments.
• Familiarity with Microsoft Entra (Azure AD),
  Intune
  , and MDM concepts, and interest in growing into these areas.
• Experience with remote support and ticketing tools (e.g., Zendesk, Jira, Freshdesk).
• Basic understanding of IT security best practices.
• Bonus Skills
  • Prior experience working within restaurant, HR & recruiting, or municipal industries (bonus).
  • Experience with macOS environments (bonus).
  • Knowledge of Share Point (bonus, not required).

• Commitment:
  Full-time, on-site in Milford, CT, with occasional travel as required
• Compensation:
  Competitive salary (depending on experience)
• Comprehensive Health, Dental, & Vision
• Paid Time Off
• Sick time
• Holidays
• Life Insurance
• 401k Contributions
• Charity Matching

Join us in this exciting opportunity to make a meaningful impact on our clients. Apply today and become an integral part of our dynamic team!