Senior Director, AI Engineering & Transformation

Rexall Pharmacy Group LTD • Mississauga, ON

41d

About The Position

Reporting to the SVP, IT & PMO, the Director, AI Engineering & Transformation will build and lead the engineering team that delivers Rexall's enterprise AI roadmap, driving measurable impact across digital, pharmacy, loyalty, store operations, and employee-facing systems.

Rexall is at the early stages of a broad, organization-wide AI transformation. This is a net-new leadership role for a senior technologist who will recruit, develop, and lead a high-performing engineering team while personally driving architecture and delivery of the highest-priority initiatives. The successful candidate views AI not as a discrete capability but as a foundational lens through which systems, processes, and decisions are continuously evaluated and improved, and has the leadership instinct to build the team that makes it real.

The initial mandate centres on assembling a delivery team and launching Rexall's first AI-native digital platforms, with supply chain, analytics, and internal tooling in scope as the team and platform mature. This role balances strategic ownership with direct delivery accountability. The Director will be accountable for building a team from the ground up, establishing engineering culture and standards, and delivering production systems in a regulated environment, while maintaining the architectural judgment to make opinionated technology decisions as the landscape evolves.

Requirements

• 10+ years of experience leading complex technology and digital initiatives, with direct accountability for delivering outcomes that materially impact business performance.
• 10+ years of experience hiring, leading, and developing high-performing technical teams, including establishing new disciplines and ways of working where capabilities were previously immature.
• Hands-on engineering fluency across modern web application stacks; this individual will write and review production code, as well as architecture diagrams. Comfortable working across frontend, backend, APIs, and data layers with the ability to ramp quickly on specific technologies as needed.
• Significant hands-on experience designing, building, and operating AI and machine-learning solutions in enterprise environments, spanning generative AI / LLMs, classical ML (predictive models, recommendation systems, optimization), and advanced analytics.
• Strong working knowledge of GenAI and agentic AI patterns including orchestration, trigger-based workflow design, and model selection with the ability to architect and deliver these capabilities in a regulated production environment.
• Demonstrated ability to take AI solutions from experimentation to reliable production use, with working knowledge of MLOps / LLMOps practices such as deployment automation, monitoring, performance management, and cost control.
• Proven ability to establish AI-assisted development practices across engineering teams, including prompt design, context management, evaluation frameworks, and review of AI-generated output.
• Hands-on fluency in AI-powered coding assistants and development tools (e.g., Claude Code, GitHub Copilot, or equivalent).
• Strong architectural judgment, with the ability to make and defend opinionated decisions related to build-versus-buy, identity and access patterns, multi-tenancy models, integration approaches, and delivery sequencing.
• Experience designing and operating scalable, high-availability systems using microservices architectures, containerization (Docker, Kubernetes), and Azure cloud services.
• Background in pharmacy, healthcare, or a similarly regulated sector (e.g., financial services) where data protection, auditability, and compliance are foundational expectations.
• Working knowledge of security, privacy, and accessibility requirements in regulated environments, including PHIPA, PCI-DSS, and AODA/WCAG, with experience embedding these considerations directly into solution design.
• Strong written and verbal communication skills, with the ability to translate complex technical decisions into clear recommendations for senior leadership.

Nice To Haves

• Pharmacy or healthcare experience is a significant advantage given Rexall's regulatory landscape.

Responsibilities

• Own and execute Rexall's enterprise AI strategy and product roadmap, spanning digital platforms, operations, and internal systems, with clear accountability for business outcomes tied to growth objectives and customer experience improvements.
• Build and lead a high-performing AI delivery team, hiring and developing talent as the mandate scales from targeted solutions to shared enterprise platforms.
• Define and establish the team's engineering operating model, development workflow, review practices, release cadence, and documentation standards, building a delivery culture optimized for AI-assisted development.
• Identify, design, and prioritize high-value AI use cases including agentic automation, GenAI workflows, predictive analytics, intelligent document processing, knowledge management, and AI-assisted decision-making, ensuring measurable impact (efficiency gains, cost reduction, revenue enablement).
• Continuously monitor applied AI advancements and industry patterns to inform Rexall's innovation roadmap and maintain competitive advantage.
• Architect and deliver core AI platform capabilities, including orchestration layers, API integrations, identity patterns, and application logic. Establish scalable, reusable patterns for enterprise adoption, leveraging leading enterprise AI platforms and LLM providers.
• Own the end-to-end AI solution lifecycle, from prototype through production, including deployment, monitoring, performance management, cost optimization, and continuous improvement.
• Establish and govern AI-assisted development practices across engineering teams, including Claude Code as the primary development engine. Set standards for prompt design, code review, output evaluation, and production readiness.
• Partner with data and platform teams to ensure data products, pipelines, quality, and governance effectively support AI use cases at scale.
• Collaborate with internal teams including Digital, Application Services, DevOps, IT Security, and Infrastructure, to transition successful prototypes into scalable, supported production systems.
• Manage external partnerships by overseeing relationships with AI vendors, cloud providers, and consulting partners, ensuring alignment with enterprise architecture standards and cost targets.
• Embed security, privacy, and responsible AI principles by design, ensuring adherence to regulatory and compliance requirements (PCI, PIPEDA, PHIPA), including transparency, auditability, and bias mitigation.

Benefits

• A closely connected culture
• A total rewards package meant to enhance your work-life flexibility
• Fully utilizing your talent
• Professional growth and development via challenging projects and assignments
• Warm and fuzzy feelings knowing you have helped your community, your team, the business and social causes through the Rexall Care Network

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 1-10 employees