Client Helpdesk Specialist

• CherryRoad Technologies is seeking to hire a highly motivated and customer-focused Client Helpdesk Specialist to provide on-site technical support while maintaining strong relationships with a client located in Middletown, NY. We are looking for an enthusiastic and motivated individual to join the team. The specialist will have ownership of video streaming services and will assist with traditional helpdesk responsibilities including helpdesk phone calls/emails/VMs and assisting with project tasks.
• 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.

• Minimum 2 years of proven experience in IT helpdesk support, desktop support, or similar role.
• Strong troubleshooting skills across Windows and common enterprise applications.
• Basic networking knowledge (LAN/WAN, VPN, Wi-Fi troubleshooting).
• Experience with audio and video equipment, including projectors and microphones.
• Familiarity with video streaming technologies and troubleshooting live streaming events using YouTube integrated with Zoom.
• Excellent communication and interpersonal skills, with the ability to interact effectively with clients and internal teams.
• 1+ year previous experience with IT ticketing tools.
• Ability to work independently on-site, managing multiple tasks and priorities effectively.
• Ability to work independently with little supervision.
• Some network experience preferred.