CherryRoad Technologies is seeking a proactive and customer-focused IT Specialist to provide hands-on technical support and lead IT initiatives for a valued client in Middletown, NY. We are looking for an enthusiastic and motivated individual to join the team. This role offers a unique opportunity to not only support day-to-day technology operations but also contribute to strategic projects within both the City and Police Department environments. Responsibilities Act as one of two primary on-site IT specialists, providing technical support to end users and resolving hardware, software, and networking issues. Deliver responsive and friendly helpdesk support for both in-person and remote users, working on-site in Middletown five days per week. Assist with IT projects such as system upgrades, deployments, migrations, and configuration updates. Contribute to the development of IT policies, procedures, and documentation. Participate in strategic initiatives including: Cybersecurity & risk management (e.g., endpoint protection, access control) Backup and continuity planning Infrastructure & network management Compliance and IT audit preparation Perform other related duties as assigned to support the client’s IT environment. Required Skills 2+ years of hands-on IT support experience in a corporate, municipal, or public-sector environment. Strong troubleshooting skills across Windows, macOS, and common enterprise applications. Solid understanding of basic networking concepts (LAN/WAN, VPN, Wi-Fi troubleshooting). Excellent communication and customer service skills with the ability to explain technical issues in non-technical terms. 1+ year previous experience with cybersecurity, risk planning, IT compliance. Ability to work independently on-site, managing multiple tasks and priorities effectively. Highly organized, proactive, and comfortable collaborating with technical and non-technical stakeholders. As a CherryRoad employee, you can expect to work with seasoned and practical experts to deliver solutions that maximize enterprise performance. And, unlike some bigger companies – where you often get lost in the crowd – at CherryRoad you can expect a refreshing and personal culture that encourages idea sharing and collaboration. Here, your knowledge, abilities, and work experience count. Your contributions are meaningful and appreciated. At CherryRoad Technologies…opportunity becomes achievement. EOE / MFDV #J-18808-Ljbffr