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.
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 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.
