Director of Information Technology and Systems

Wills Transfer is seeking a forward-thinking Director of Information Technology and System s to help us harness the power of technology to transform warehousing and logistics. This is a greenfield opportunity to shape the future of how we use technology – especially artificial intelligence – to drive efficiency, reliability, and customer value across our operations. THE OPPORTUNITY Reporting directly to the President, this role will lead our internal Technology & Systems team, manage vendor relationships, and guide our company through an exciting evolution toward smarter, more connected operations. The successful candidate will have hands-on experience leveraging AI-driven tools or systems to improve operational efficiency and decision-making. They will also lead the evolution of our current Warehouse Management System (WMS) and determine whether it continues to meet the needs of our growing and increasingly digital business. Equally important, this role will serve as a key client-facing partner, ensuring that Wills remains an industry leader in system-to-system integration. The ideal candidate will have the ability to speak both “technology” and “operations,” translating complex systems into client value and ensuring seamless collaboration between Wills’ platform and our customers’ systems. KEY AREAS OF IMPACT Strategic Technology Leadership Build and execute a forward-looking technology roadmap for Wills Transfer, with an emphasis on automation, AI, and data-informed decision-making. Oversee day-to-day IT operations while also setting the strategic direction for technology advancement across all branches. Client-Facing Collaborations Serve as a primary point of contact for client system integrations and digital initiatives. Collaborate with customers to design, test, and implement seamless technology connections between Wills’ WMS and their internal systems. Proactively identify integration opportunities that improve transparency, efficiency, and service quality for our clients. AI Innovation & Integration Identify opportunities to implement AI and machine learning to improve warehouse efficiency, predictive maintenance, demand forecasting, and data visibility. Evaluate and deploy AI-driven tools that enhance client experiences, streamline workflows, and improve safety and performance. WMS & System Optimization Assess and optimize our current WMS; lead the process of evaluating alternative solutions if appropriate. Oversee system configuration, performance, and integration with clients’ systems. Greenfield Implementation & Change Leadership Design and implement scalable technology infrastructure and digital systems where none currently exist. Guide the organization through a digital transformation journey – building buy-in, adoption, and alignment at every level. This is a full-time, onsite role based in Eastern Ontario, with regular travel between our 7 Ottawa-area branches. The successful candidate will spend time in the field, building relationships and understanding frontline operations firsthand to ensure systems and technology solutions are aligned and adopted. IDEAL CANDIDATE 7 years of progressive IT experience, including leadership of internal teams and external vendors. Proven experience leveraging AI, automation, or advanced analytics to improve operational or business outcomes. Deep understanding of WMS platforms and system integrations within warehousing, logistics, or supply chain environments. Strong technical knowledge coupled with the ability to communicate clearly with both technical and non-technical stakeholders. Demonstrated ability to evaluate, implement, and manage new technologies in greenfield environments. Experience leading client-facing system integration projects, ideally within a multi-site or logistics setting. WHY JOIN WILLS TRANSFER? We’re a values-driven company with deep roots in Eastern Ontario. This is a unique opportunity to join a stable, growing business and lead meaningful technology improvements that will shape how we deliver value to our customers.

Location: Smiths Falls, Ontario, CA

Posted Date: 11/4/2025