Senior IT Helpdesk Specialist

Senior IT Helpdesk Specialist Advanced Hospitality•4.0 Milford, CT Job Details Full-time From $65,000 a year 1 day ago Benefits Paid holidays Health insurance Dental insurance Paid time off Vision insurance 401(k) matching Life insurance Qualifications Technical documentation Process improvement Windows Computer networking macOS IT Full Job Description This position is onsite in Milford, CT.•

DESCRIPTION

We are looking for an experienced Senior IT Helpdesk Specialist to provide high-level technical support for onsite and remote employees, manage Microsoft 365 environments, and support onboarding, system maintenance, and IT operations. 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. Microsoft Ecosystem & Onboarding 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. Documentation & Process Improvement 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. Maintenance & Security 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. Project Support Support IT setup and system configuration for new office or client locations (occasional travel). Assist in technology rollouts and adoption of new solutions.

QUALIFICATIONS

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. Prior experience working within restaurant, HR & recruiting, or municipal industries (bonus). Experience with macOS environments (bonus). Knowledge of SharePoint (bonus, not required).

Hours & Compensation 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!

Pay:

From $65,000.00 per year

Benefits:

Dental insurance Health insurance Paid time off Vision insurance

Work Location:

In person