Senior IT Helpdesk Specialist

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.

Do you have experience in Windows?, * 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

Pulled from the full job description

• Health insurance
• 401(k) matching
• Paid time off
• Vision insurance
• Dental insurance
• Life insurance
• Paid holidays, * 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