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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Senior IT Helpdesk Specialist - **Company:** Advanced - **Location:** Milford, CT, United States - **Experience:** Expert - **Salary:** $65,000.0 - **Contract:** Permanent contract - **Skills:** Microsoft Windows, JIRA, Microsoft Online Services, Cyber Security, System Configuration, Identity and Access Management, Issue Tracking Systems, IT Management, Information Technology Operations, Networking Basics, Azure Active Directory, Microsoft SharePoint, Reliability of Systems, Microsoft InTune, Zendesk - **Published:** May 20, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=55f88c615b48aa99 ## About the Role 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 ## 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. ## Related Videos - [Improving quality with Agentic AI with Rovo Dev and Xray](https://www.wearedevelopers.com/videos/2005-improving-quality-with-agentic-ai-with-rovo-dev-and-xray) - [The AI Agent Path to Prod: Building for Reliability](https://www.wearedevelopers.com/videos/1523-the-ai-agent-path-to-prod-building-for-reliability) - [Your Manager Doesn’t Come with a User Manual (But You Can Totally Write One)](https://www.wearedevelopers.com/videos/1495-your-manager-doesn-t-come-with-a-user-manual-but-you-can-totally-write-one) - [Beyond the 9–5: Designing Work Around Humans](https://www.wearedevelopers.com/videos/1321-beyond-the-9-5-designing-work-around-humans) - [Engineering/Manager Pendulum: Generating compound interest on your career](https://www.wearedevelopers.com/videos/100348-engineering-manager-pendulum-generating-compound-interest-on-your-career) - [Navigating the Corporate Jungle: Life as a Developer in a large Company](https://www.wearedevelopers.com/videos/621-navigating-the-corporate-jungle-life-as-a-developer-in-a-large-company) ## Related Articles - [Fully Remote Software Engineer Jobs](https://www.wearedevelopers.com/magazine/447-fully-remote-software-engineer-jobs) - [The Best Job Search Websites of 2025](https://www.wearedevelopers.com/magazine/368-the-best-job-search-websites-of-2025) - [The Most Popular IT Jobs on the Market](https://www.wearedevelopers.com/magazine/376-the-most-popular-it-jobs-on-the-market) - [Finding IT & Technology English-speaking Jobs in Germany ](https://www.wearedevelopers.com/magazine/446-finding-it-technology-english-speaking-jobs-in-germany) - [Where to Find Entry-Level Software Engineering Jobs](https://www.wearedevelopers.com/magazine/397-where-to-find-entry-level-software-engineering-jobs) - [Is Software Engineering Over-Saturated?](https://www.wearedevelopers.com/magazine/418-is-software-engineering-over-saturated)