Sr. Director, Product Management, Healthcare Technology

Please note Loblaw's hybrid work model is 4 days in office

Sr. Director, Product Management, Healthcare Technology | Brampton ON

We are looking for a passionate and dedicated Senior Director to help drive Technology Delivery and Operations for our Healthcare Technology products. This position works in partnership with different business lines — Pharmacy Services, Digital and Specialty Systems among others — and collaborates closely with the Pharmacy team to ensure applications across both portfolios operate seamlessly and in a unified manner. You will play a strategic role in the modernization and evolution of products that will make a significant and lasting impact on Canadians. You will be accountable for the stability, resilience, and continuous improvement of our Healthcare applications, ensuring end users have an optimal experience through streamlined operations, meaningful metrics, and accelerated innovation.

What You Will Do:

• Drive the full technology lifecycle on the Health Technology Portfolio — from Product Discovery and solution design through development, testing, and production implementation — working in close partnership with Digital, Specialty Systems, and Pharmacy Services business lines to ensure alignment at every stage.
• Bring technological breadth and depth to a diverse, complex portfolio spanning SaaS solutions, third‑party integrations, and in‑house built applications — understanding the distinct demands of each and making sound architectural and operational recommendations across all of them.
• Work closely with strategic vendors to deploy new pharmacy platforms and applications, ensuring adherence to best‑in‑class cybersecurity standards and high system availability and resilience.
• Manage a budget of over $20MM and ensure the right resource mix is aligned with our cost to serve principles.
• Lead process and methodology improvements that remove friction for development teams, accelerate delivery, and keep strategic initiatives on track.
• Define and drive a forward‑looking roadmap that balances operational excellence with rapid innovation, including full financial oversight of the team's portfolio.
• Champion advances in system monitoring, observability, and tooling to stay ahead of issues before they impact end users.
• Govern all production changes and audits, ensuring systems are well‑documented, diagrams are accessible, and integration standards are upheld.
• Oversee Quality Engineering to enforce low‑to‑zero defect leakage and strong automated test coverage.
• Lead, coach, and grow a high‑performing team — setting a culture of accountability, curiosity, and continuous improvement.
• Navigate complex stakeholder environments with confidence — aligning competing priorities, driving decisions, and influencing outcomes across business and technology lines.

What You Will Need:

• Undergraduate degree in Computer Science or equivalent; what matters most is what you've built and led.
• Proven track record leading enterprise‑scale IT Development, Operations and Support, with experience managing mixed teams of employees, onshore, and offshore contractors.
• Strong leadership presence — able to inspire, challenge, and grow talent while holding teams to a high standard.
• A natural collaborator and skilled conciliator who thrives in a matrixed environment, building bridges across Digital, Specialty, Pharmacy, and executive stakeholders.
• Hands‑on depth in Agile, DevOps, and CI/CD practices, with a strong Quality Engineering mindset.
• Experience with observability and performance platforms (Dynatrace, AppDynamics, Splunk) and issue tracking tools (ServiceNow, JIRA, Confluence).
• Familiarity with Google GCP, VM infrastructure, physical store hardware, and test automation technologies.
• Entrepreneurial energy — eager to make a difference, move fast, and leave things better than you found them.
• Prior experience within the Canadian Healthcare ecosystem is considered a strong asset.
• This is a people‑first leadership role. Our teams are spread across several offices within the GTA, and we believe great cultures are built in person — mandatory in‑office presence 4 days per week is expected.
• Ability and willingness to travel 10–15% of the time within Canada to support team collaboration, stakeholder engagement, and cross‑site initiative.

Accommodation in the recruitment, assessment, and hiring process is available upon request for applicants with disabilities.

Applicants who are 18 years or older are required to complete a criminal background check. Details will be provided through the application process.

Hiring Range: $170,000.00 – $220,000.00 per year.