Akira Chicago Jobs (NOW HIRING)

AKIRA Director of Corporate IT

AKIRA is one of the fastest-growing fashion retailers in the country — 35+ stores, a high-octane e-commerce business, a corporate HQ, and a Bolingbrook distribution center, all headquartered in Chicago. We move fast, ship trends faster, and run lean. Here, technology is a competitive weapon, not a back-office afterthought — the systems behind our HQ and warehouse power a business that is scaling every quarter. We're looking for a builder: a hands-on, forward-thinking leader who wants to modernize how a growing company runs and make a visible impact doing it.

Position: Director of Corporate IT

Location: Chicago, IL (corporate office) or Bolingbrook, IL (warehouse) — on-site daily; not remote

Position Summary

The Director of Corporate IT owns the infrastructure, security, identity, and support that keep AKIRA's Chicago HQ and Bolingbrook warehouse running — but the mandate goes well beyond keeping the lights on. This is a role for someone who is constantly asking, “how do we do this better, faster, and smarter?” — automating manual work, piloting AI where it creates real leverage, and bringing back winning technologies that give a growing company an edge. You'll lead high-impact projects, keep our systems rock-solid and secure, and help set the technology roadmap for what's next. This is a hands-on, on-site role: the Director works daily from either the Chicago corporate office or the Bolingbrook warehouse. This is not a remote position. The role reports to the Chief Operating Officer and partners closely with the Software Development and Store Technology teams.

Key Responsibilities

1. Project Management Leadership

• Lead complex IT projects hands-on, using Agile, Kanban, and traditional methodologies to deliver results within timelines and budgets.

• Act as the primary coordinator across corporate IT — defining priorities and managing projects from initiation through completion while optimizing resources.

• Regularly report progress, risks, and deliverables to executive leadership, maintaining clear communication with all stakeholders.

2. Innovation & Automation

• Continuously hunt for better ways to run the business — spot manual, repetitive, or broken workflows and automate them across corporate systems.

• Pilot and deploy AI tools and agents that create real leverage — from help-desk automation and document processing to reporting, onboarding, and internal productivity.

• Stay ahead of the curve: attend industry trade shows and events, evaluate emerging technologies, and bring back winning solutions that give a fast-growing retailer a competitive edge.

• Build a culture of experimentation — test fast, measure impact, and scale what works across the organization.

3. Corporate & Warehouse Infrastructure

• Own corporate IT infrastructure and security for both the Chicago office and the Bolingbrook warehouse — ensuring stability, security, and efficiency across all systems.

• Manage the network across both facilities on Cisco Meraki — SD-WAN, firewalls, switches, access points, VLAN design, guest segmentation, and Wi-Fi performance for staff and warehouse devices.

• Administer Google Workspace as AKIRA's core productivity and identity platform — user lifecycle, security groups, MFA/SSO, drive governance, and email security.

• Manage corporate endpoints and device lifecycle — imaging, standards, refresh cadence, asset inventory, and endpoint protection.

4. Help Desk & Support Services

• Oversee help desk operations using Freshservice to streamline support workflows, ticket routing, and knowledge management for corporate and warehouse end users.

• Set and monitor SLAs, using data-driven insights to continuously improve response times and user satisfaction.

5. Business Systems & Security

• Support and safeguard the SaaS ecosystem the business runs on, including NetSuite (ERP), Shopify POS, iSolved / HighFlyer (HRIS/payroll), StoreForce (scheduling), Slack, Teamtailor (ATS), and DocuSign — including access provisioning, integrations, and vendor coordination.

• Implement and manage security and identity best practices — identity and access management, MFA, least-privilege access, endpoint protection, and data integrity — and maintain PCI-DSS awareness where corporate and warehouse systems touch payment or cardholder scope.

6. Vendor Management & Negotiation

• Build and maintain strategic relationships with hardware, software, and connectivity vendors, negotiating contracts that align with AKIRA's needs and budget.

• Hold third-party vendors and MSPs accountable to service agreements and standards, optimizing cost efficiency and service quality.

7. Cross-Functional Collaboration

• Serve as the primary corporate IT leader for both the Chicago office and the Bolingbrook warehouse, supporting day-to-day operations and technology alignment across both locations.

• Partner closely with the Development team and the Store Technology team to align initiatives and support corporate systems effectively, and work cross-functionally with Finance, HR, and Operations.

Required Qualifications

• Bachelor's degree in Computer Science, Information Technology, or a related field.

• Minimum of 8+ years in IT management roles, with a track record of managing corporate infrastructure, security, and help desk operations.

• Extensive project management experience, with proven expertise in Agile, Kanban, and traditional methodologies.

• A demonstrated bias for innovation and automation — a real track record of streamlining operations, deploying AI or automation to eliminate manual work, and championing new technology in a fast-moving environment.

• Hands-on proficiency with Google Workspace administration, Cisco Meraki networking, identity and access management, and Freshservice (or comparable ITSM). You must be technical.

• Demonstrated ability to perform technical configurations and troubleshooting across cloud, network, identity, and security solutions.

• Strong experience in vendor management and negotiation, with a history of cost-effective, high-quality partnerships.

• Exceptional organizational, communication, and leadership skills, with a collaborative approach to cross-functional projects.

Preferred Qualifications

• Experience in a multi-site retail, e-commerce, or distribution environment, including warehouse/DC technology.

• Industry certifications such as CompTIA Network+/Security+, Cisco/Meraki (CMNA), Google Workspace Administrator, or PMP.

• Familiarity with NetSuite, Shopify, and PCI-DSS in a retail merchant environment.

• Experience integrating SaaS platforms and building automation across business systems.

• A habit of scouting emerging technology at trade shows and industry events and turning it into practical, high-ROI wins.

Location & Work Requirements

This role requires daily on-site presence at either the Chicago corporate office or the Bolingbrook warehouse. This is not a work-from-home position; the Director of Corporate IT is expected to lead operations in person to ensure direct oversight of both locations.

Benefits & 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.

Employment Type: Full-Time, Exempt

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.