AKIRA Director of Corporate 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.

Department IT Role Director of IT Locations Chicago Headquarters Yearly salary $135,000 - $200,000 Employment type Full-time