Strategic CTO Multi-Site Retail & Distribution

Description

Kelli’s and Cloverkey are seeking an experienced, hands-on Chief Technology Officer (CTO) to lead the technology strategy for both businesses. Reporting to the President as a member of the executive team, the CTO will oversee technology across Kelli’s wholesale distribution operations and Cloverkey’s growing fleet of hospital gift shops. This includes store systems, point-of-sale and payments, warehouse and distribution systems, internal applications, data and reporting, infrastructure, the service desk, and cybersecurity.

The ideal candidate is a practical, strategic leader with strong business acumen and a proven record of supporting multi-site retail and distribution operations while leading high-performing technical teams.

Kelli’s is a trusted wholesale distributor serving hospital gift shops and retailers nationwide, while Cloverkey operates a growing fleet of hospital gift shops. Together, we live by a shared promise: We Give More. For both businesses, that means going further for our customers, hospital partners, and team members through exceptional service, thoughtful solutions, and a commitment to doing things right. We’re looking for a leader who shares those values and can help both companies grow.

This position is based in our office daily. We do not offer remote opportunities.

Key Responsibilities:

Strategic Leadership

• Develop and execute a multi-year technology roadmap aligned with business goals, including store growth and platform modernization.
• Serve as the technology advisor to the President and executive team, translating technology options, risks, and costs into clear business decisions.
• Foster a culture of accountability, documentation, and continuous improvement across the technology team.

Team Leadership & Operations

• Lead, mentor, and develop the technology team, including IT operations, the service desk, and application development; build an organizational structure that scales with the business.
• Oversee system architecture decisions, development practices, infrastructure, and software implementation.
• Own service desk performance for store and corporate users, with defined service levels and regular reporting.
• Ensure technology standards, documentation, and best practices are maintained across the organization.

Retail, Store & Business Systems

• Own the point-of-sale, ERP, and payments platforms across a growing network of retail locations, including platform upgrades and payment terminal and gateway migrations.
• Direct technology deployment for new store openings, coordinating connectivity, hardware, and systems with hospital IT and facilities partners.
• Partner with Operations, Sales, and Finance on internal applications, warehouse systems, and reporting and analytics that improve store and business performance.
• Identify and evaluate new technologies, including AI tools, that can give the company a competitive edge.

Security & Compliance

• Ensure the security, privacy, and integrity of company data and technology assets.
• Lead the security program against a recognized framework (CIS Controls), including PCI DSS compliance for card-present payments.
• Own backup, disaster recovery, and incident response capabilities, and lead responses to customer and partner security reviews.
• Establish and enforce policies and procedures, including AI acceptable use and data governance, that maintain regulatory compliance and manage risk.

Budgeting & Vendor Management

• Develop and manage the technology capital and operating budgets.
• Evaluate, negotiate, and manage relationships with vendors, dealers, and managed service providers.

Requirements

Qualifications:

• Bachelor’s degree in Computer Science, Information Systems, or a related field, or equivalent experience (MBA a plus).
• 10+ years of…