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.

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. 

Qualifications:

• Bachelor’s degree in Computer Science, Information Systems, or a related field, or equivalent experience (MBA a plus). 
• 10+ years of progressively responsible technology experience, including at least 5 years leading an IT function. 
• Proven experience leading technology for multi-site retail, distribution, or similar operations, including point-of-sale, ERP, and payments platforms. 
• Hands-on ability to diagnose problems and do the technical work directly; this is a player-coach role on a small team. 
• Strong understanding of system architecture, cloud infrastructure, networking, data platforms, and cybersecurity. 
• Working knowledge of PCI DSS and a recognized security framework (CIS Controls, NIST CSF, or similar). 
• Experience negotiating vendor contracts and overseeing managed service providers. 
• Excellent leadership, interpersonal, and communication skills, including the ability to explain technology decisions to non-technical executives. 

Preferred Attributes:

• Entrepreneurial mindset suited to a family-owned, growing company. 
• Track record of building and scaling teams and processes through rapid location growth. 
• Experience with NCR Counterpoint or a comparable retail POS/ERP platform. 
• Experience supporting retail operations located inside hospitals or other host-site environments. 
• Comfortable working in a dynamic, fast-paced, and collaborative environment. 
• Passion for leveraging technology to improve customer experience and business performance.

Kelli’s is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state, or local law.