Senior IT Field Technician

AKIRA Senior IT Field Technician

In 2002, AKIRA opened the doors to its first women's clothing boutique in Chicago. Since then, the company has extended its reach to 40+ stores across the United States, as well as a thriving eCommerce business ( shopAKIRA.com ). AKIRA is extremely well-poised for sustained growth as we continue to build a nationally recognized brand.

AKIRA's culture has one very large, distinct difference from other fast-fashion competitors: Other-Worldly Customer Service and Fanatical, Obsessive Attention to the consumer's needs and desires. The core principle for all employees at AKIRA is to Act and Think Like an Owner, and this belief can be reflected across all areas of the company.

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

P osition Overview:
AKIRA is seeking a seasoned Senior IT Field Technician to lead the hands-on installation, deployment, and infrastructure support of technology across our 40 retail stores. This is a field-first, travel-heavy role (approximately 50%) for someone who is at their best on the floor of a store — racking network gear, standing up POS lanes, running and certifying connectivity, and getting a new or remodeled location live and stable.

This is a senior individual-contributor role, not a management position. The ideal candidate is the most experienced technical hand in the field: they own complex installs end-to-end, set the standard for how store technology is deployed, and mentor Level 1 and Level 2 technicians by example — but they do not have direct reports. They work independently across multiple markets, coordinate vendors and ISPs on site, and partner with the IT Manager on deployment planning and standards.

Essential Responsibilities

Field Installations & Store Deployments (Primary Focus)

• 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

• Coordinate 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 Required

• 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).

• Ability 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:

AKIRA offers 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.

Benefits and Perks:
AKIRA offers 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

We are committed to fair and transparent compensation practices. Compensation for this position will be determined based on experience, qualifications, and other job-related factors. Additional compensation and benefits may also apply and will be discussed during the hiring process.

We may utilize AI-assisted and automated tools as part of the recruiting and hiring process. All employment decisions are made in compliance with applicable laws and without discrimination.