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:

o   Cybersecurity & risk management (e.g., endpoint protection, access control)

o   Backup and continuity planning

o   Infrastructure & network management

o   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