IT Specialist

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 Include

• 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