Director of IT – Multi-Site Retail Organization (Remote)

Salary: $140,000 - $170,000

Location: Remote with up to 10% annual travel. Must reside in the United States, ideally in Central or Eastern time zones.

Join a rapidly growing, technology-forward multi-site retail company operating 75+ locations across the Midwest with aggressive expansion plans to surpass 100+ locations over the next several years. Our client is building a high-performance network powered by people, automation, and smart technology. This role is an opportunity to influence IT strategy, modernize systems, and shape the technology foundation that supports a large and expanding retail footprint.

We are seeking a Director of Information Technology to oversee all technology operations across a multi-state retail environment. This leader will ensure secure, reliable, and scalable IT systems while serving as the primary liaison between internal stakeholders, external MSP partners, and POS vendors. The role centers on vendor management, IT governance, infrastructure oversight, and strategic project delivery.

Responsibilities

Vendor & Partner Management

Serve as the primary point of contact for MSP and POS vendors.
Monitor SLAs, review performance metrics, and escalate issues when needed.
Oversee contract negotiations and manage renewals.

IT Governance & Oversight

Ensure MSP partners follow security standards, compliance requirements, and industry best practices.
Maintain visibility across incident management and change-control processes.

Infrastructure & Systems Coordination

Oversee network connectivity, hardware lifecycle management, and POS system integrations across all retail locations.
Coordinate deployments, upgrades, and troubleshooting with MSP and technology partners.

Project Management

Lead IT workstreams for new site openings, system migrations, and technology rollouts.
Develop project plans, timelines, budgets, and communication strategies for internal stakeholders.

Strategic Planning

Evaluate emerging technologies and recommend solutions to improve operational efficiency across the retail network.
Build and manage IT budgets and forecast future technology needs.

Documentation & Reporting

Maintain IT asset inventories, vendor documentation, and system records.
Provide regular IT performance reporting, risk assessments, and recommendations to leadership.

Qualifications

Bachelor’s degree in Information Technology, Computer Science, or related field (or equivalent experience).
10+ years of IT experience, including vendor management and project leadership.
Experience in multi-location retail, service, hospitality, franchise, or field-operations environments required.
Familiarity with MSP-driven environments and POS systems (retail preferred).
Strong understanding of networking, Windows environments, and cloud services.
Knowledge of cybersecurity standards and compliance frameworks, including PCI DSS.
Excellent communication, leadership, and stakeholder-management skills.
Experience with Intune, RMM platforms, and remote management tools preferred.
Background in multi-location retail, service, hospitality, franchise, or field-operations environments.
Project Management Certification (PMP or similar) preferred.

Compensation & Benefits

Competitive base salary with bonus opportunities
Employee discounts on company services
Paid time off
Health, dental, and vision insurance
Comprehensive training and advancement opportunities in a rapidly scaling organization
A strong, people-first team culture focused on growth and customer excellence
Compensation depends on relevant experience and/or education, specific skills, function, geographic location, and other factors applicable by law (for example: state minimum wage thresholds). The expected base rate for this role is between

Work Environment

Remote work setting
Evening and weekend availability as business needs require
On-call responsibility for high-priority escalations
Occasional regional travel to retail locations and leadership meetings

The Company is committed to equal employment opportunity for all employees and applicants. We do not discriminate based on race, color, creed, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity, marital or family status, veteran status, age, national origin, ancestry, physical or mental disability (including HIV/AIDS), medical condition, genetic information, participation in human rights activities, status with regard to public assistance, or any other characteristic protected by law. All employment decisions—including recruitment, selection, training, compensation, benefits, promotions, discipline, transfers, lay-offs, returns from lay-off, terminations, and all other programs—are based solely on valid job-related requirements.

Addison Group

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