Senior Deskside Technician

Location: New York, NY
Employment Type: Full-Time, Long-Term (Indefinite)
Start Date: January 2, 2026
Work Schedule:

• Holiday period:
  Tuesday–Saturday, shifts may extend up to 9:00 PM

• Post-holiday:
  Monday–Friday, 8:00 AM or 9:00 AM – 5:00 PM

• Flexibility with schedule is strongly preferred

• Onsite 5 days per week

We are seeking a Senior Deskside Technician / Technical Services Support Analyst to provide onsite technical support and oversight for a high-profile retail environment. This role supports both existing and newly deployed technologies and partners closely with internal IT teams, operations, and external vendors to ensure reliable service delivery.

The ideal candidate has a strong technical background, adapts quickly to new technologies, and is comfortable working in a fast-paced, customer-focused environment. A strong emphasis is placed on Point of Sale (POS) systems, automated inventory solutions, and hands-on onsite support.

Infrastructure & Technology Support (35%)

• Manage delivery, support, and lifecycle management of infrastructure technologies, including:

  • Point of Sale (POS) systems

  • Endpoint devices (PCs, Macs, mobile devices, printers, telephones)

  • Software deployment, updates, and maintenance

• Support new technologies, applications, and processes as they are introduced

Automated Inventory Systems Support (35%)

• Provide hands-on technical support for automated inventory management systems in coordination with remote vendors

• Develop detailed operational guides, work instructions, and technical documentation to internalize support

• Perform routine system checks and provide daily/weekly status reporting

Hardware Deployment & Requests (10%)

• Fulfill and manage hardware requests, including:

  • PCs and laptops

  • Printers

  • POS and payment devices

• Perform installations directly or coordinate deployments with vendors

Process Improvement & Documentation (10%)

• Identify gaps in processes and knowledge base documentation

• Partner with IT and Operations to develop documentation that supports issue prevention and knowledge sharing

• Coordinate and support training for new and existing employees

Service Delivery & Stakeholder Management (10%)

• Manage relationships with internal teams and external partners

• Proactively follow up on incidents to ensure resolution within agreed SLAs

• Support incident, problem, and change management activities

• 4–6+ years of experience in IT support and service delivery

• Strong experience with:

  • Windows 10 & 11

  • Apple iOS

  • Microsoft 365 tools

• Experience with Active Directory and user/endpoint management

• Command-line experience (e.g., Power Shell)

• Experience supporting automated systems

• Excellent verbal and written communication skills with strong attention to detail

• Strong analytical, problem-solving, and multitasking abilities

• Ability to build and maintain effective business partnerships

• Ability to approach technical challenges from a business perspective

• Proven ability to establish technical credibility with users, peers, and engineers

• Bachelor's degree in Information Technology or equivalent certifications

• Experience with software management and distribution

• Experience with video conferencing and collaboration technologies

• Networking experience, including:

  • Cisco/Meraki switching and wireless

  • IP addressing, subnetting, and assignment

• General awareness or experience with:

  • PLC operations

  • HMI panels

• This role requires consistent onsite presence and may involve working outside normal business hours, including weekends, to support projects and peak periods.