Senior IT Field Technician

Position Overview

The Position: Senior IT Field Technician
Location: HQ - Chicago, IL (On-Site)
Reports To: Store IT Manager

Essential Responsibilities

• Serve as the lead on-site technician for new store openings, remodels, relocations, and pop-ups — from pre-build planning through go-live and post-launch stabilization.
• Install, configure, and test complete store technology stacks, including: POS registers, payment terminals, and lane peripherals
• Network hardware — firewalls, switches, and wireless access points
• iPads, tablets, scanners, receipt/label/Zebra printers, and security towers
• Back-office workstations and supporting devices
• Cook up low-voltage cabling, ISP circuit installs/turn-ups, and structured wiring with landlords, GCs, and third-party vendors on site.
• Conduct wireless site surveys and validate coverage, throughput, and failover before handing a store to operations.
• Own the deployment checklist for each project and confirm every system is functional, documented, and standardized before sign-off.
• Network & WiFi Infrastructure
• Act as the senior hands-on resource for store networking — Meraki firewalls, switches, and access points (configuration, troubleshooting, replacement).
• Diagnose and resolve connectivity, WiFi coverage, VLAN, and ISP/circuit issues, escalating to carriers and managing the ticket to resolution.
• Maintain network standards across the fleet and remediate stores that deviate from the standard build.
• Store Technology Support & Escalations
• Resolve complex, high-impact POS, hardware, and connectivity issues that Level 1/Level 2 cannot — in person or remotely.
• Provide direct, calm support to store teams to minimize downtime and protect sales operations.
• Manage device lifecycle in the field: staging, deployment, swaps, RMAs, and decommissioning; keep hardware and loaner inventories accurate.
• Technical Leadership (Individual Contributor)
• Set the standard for how installs and store technology are deployed; build and maintain deployment playbooks, runbooks, and SOPs.
• Mentor and upskill Level 1 and Level 2 technicians in the field — by guidance and example, without direct management responsibility.
• Partner with the IT Manager on deployment scheduling, hardware standards, vendor selection, and project planning.
• Identify recurring field and infrastructure issues and drive permanent, root-cause fixes.
• Documentation & Continuous Improvement
• Create and maintain accurate technical documentation, store network diagrams, and knowledge-base articles.
• Track project work and field activity in the Service Desk (Freshservice) with thorough notes.
• Recommend improvements that reduce install time, ticket volume, and downtime.

Qualifications

• 5+ years of hands-on IT support experience, with significant time spent on field installations and deployments (retail or multi-location strongly preferred).
• Demonstrated installation experience — standing up POS, network, and peripheral hardware at physical sites, not just remote/help-desk support.
• Strong networking skills: firewalls, switches, access points, VLANs, WiFi, and ISP/circuit troubleshooting (Meraki experience strongly preferred).
• Able to travel approximately 50% of the time, including occasional overnight and multi-day trips for store projects.
• Valid driver’s license, clean driving record, and reliable transportation.
• Able to perform the physical demands of installs — lift/move equipment (up to ~50 lbs), use ladders, and work in active construction/retail environments.
• Experience owning a ticket queue and working independently across multiple locations.
• Excellent communication and the ability to explain technical steps clearly to non-technical store teams.
• Willingness to provide after-hours and weekend support around openings, launches, and emergencies.

Preferred

• Cisco Meraki certification (CMNA) or equivalent networking certification (CompTIA Network+, Security+).
• Hands-on experience supporting Shopify POS environments and payment peripherals.
• Low-voltage cabling experience and familiarity with structured wiring standards.
• Experience with Apple device management (iPads, iOS, macOS) and MDM.
• Prior experience leading new-store technology buildouts at scale.

Benefits And Perks

• Competitive benefits for full-time employees, including Medical, Dental, Vision, Pet Insurance, Life, LTD, FSA/HSA/Dependent Care FSA, Flex Transit (CTA), 401(k), and a generous employee discount.
• We’re committed to internal growth, providing meaningful development and career advancement opportunities.

Job Type

Full-Time

Additional Compensation and Benefits

All employment decisions are made in compliance with applicable laws and without discrimination. At AKIRA, we believe in breaking down the barriers of the traditional retail experience and embracing the individuality of both our team and our clients. We’re on the lookout for extraordinary individuals who thrive on creativity, innovation, and pushing the boundaries of what's possible. Join our team and become part of a culture that values diversity, fosters personal growth, and encourages out-of-the-box thinking.