Client & Role Background

Our client is a large, rapidly expanding multi‑location specialty retailer with several hundred corporately owned stores across the United States and a multi‑facility distribution network. The organization is undergoing an important scaling phase following recent, significant multi‑market expansion.

The next stage of growth requires modernizing its enterprise technology capabilities, strengthening digital enablement, and ensuring operational systems can support a national retail footprint. The company seeks a Chief Information Officer (CIO) to architect and lead a comprehensive transformation of enterprise technology across a complex, multi‑state environment.

Reporting to the Chief Executive Officer, the CIO will serve as the senior-most technology leader, responsible for enterprise applications, store systems, infrastructure, cybersecurity, data & analytics, integrations, and the long‑term IT roadmap. The role requires an executive who can balance strategic planning with hands‑on, execution‑focused leadership in a lean operating environment.

Role Responsibilities

Technology Strategy & Enterprise Leadership

Develop and execute a long‑term technology roadmap aligned with enterprise growth, operational priorities, and evolving omnichannel needs.
Maintain a high‑velocity, agile IT operating model capable of rapid reprioritization.
Lead, mentor, and develop a lean but high-performing IT organization (including enterprise systems, infrastructure, support, and development personnel).
Serve as a strategic advisor to senior leadership, ensuring technology investments drive measurable business outcomes.

Store Systems, Infrastructure & Modernization

Oversee modernization of store technologies, including hardware, connectivity, and device management across a large retail footprint.
Drive ongoing cloud migration initiatives, reducing on-premises infrastructure and increasing scalability and resilience.
Ensure strong reliability and evolution of all store systems, POS environments, and customer‑facing operational technologies.

Enterprise Applications, Integrations, & Data

Provide governance and leadership over the enterprise ERP platform, ensuring performance, stability, and continuous optimization.
Oversee integrations, middleware, partner systems, and data flows across a broad ecosystem.
Lead development and enhancement of internal tools, mobile apps, and productivity applications used by associates and store teams.
Establish data governance, BI standards, reporting quality controls, and analytics capabilities that support decision-making across operations, merchandising, supply chain, and finance.

M&A Technology Integration

Lead the integration of acquired stores, business units, or operating groups into the enterprise technology ecosystem.
Standardize repeatable playbooks for system migration, infrastructure build‑outs, onboarding accelerations, and consolidation of disparate technology environments.

Cybersecurity, Risk & Compliance

Oversee enterprise cybersecurity, ensuring that controls, policies, and safeguards are appropriate for a large national retailer.
Implement operational resilience programs, including incident response, risk assessments, and endpoint security measures.
Ensure compliance with all relevant standards, internal policies, and regulatory expectations.

Vendor & Partner Management

Manage critical relationships with hosting providers, infrastructure services, systems integrators, and application vendors.
Ensure performance against SLAs while maintaining cost effectiveness.
Oversee contract negotiations and budget alignment across all technology domains.

Culture, Team Development & Hands‑On Leadership

Lead by example in a culture that values hands‑on involvement, agility, and responsiveness.
Develop and mentor technology staff to deepen capabilities and expand ownership across disciplines.
Foster a collaborative, fast‑moving, accountable environment aligned with the company’s operational ethos.

Role Requirements

Executive-level IT leadership experience in multi‑location retail, consumer, distribution, or similarly complex operational environments.
Expertise across POS systems, ERP platforms, digital commerce integrations, store networks, and retail operational technologies.
Track record driving cloud migrations, infrastructure modernization, and scalable enterprise architecture improvements.
Demonstrated success leading M&A technology integrations, consolidations, and onboarding efforts.
Strong financial discipline managing capital and operating budgets within a high‑growth enterprise.
Prior experience in private equity–backed or fast‑paced, performance-driven environments strongly preferred.
Experience building lean, high-impact teams with strong development and mentoring capability.
Bachelor’s degree required; advanced technical or business degree preferred.

Role Location & Travel

The role is based at the company’s primary operating hub in the Mid‑Atlantic region. Significant travel to stores, distribution centers, and partner locations is required. Exceptional remote candidates may be considered with a willingness to travel frequently.

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