Sr. Director, Product Management, Healthcare Technology

Loblaw Companies Limited•Brampton, ON

8d•Hybrid

About The Position

Loblaw Companies Limited is seeking a passionate and dedicated Senior Director to drive Technology Delivery and Operations for their Healthcare Technology products. This role involves partnering with various business lines such as Pharmacy Services, Digital, and Specialty Systems, and collaborating closely with the Pharmacy team to ensure seamless application operations. The position plays a strategic part in modernizing and evolving products that will significantly impact Canadians. The Senior Director will be accountable for the stability, resilience, and continuous improvement of Healthcare applications, ensuring an optimal end-user experience through streamlined operations, meaningful metrics, and accelerated innovation.

Requirements

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 (e.g., 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.
Ability and willingness to travel 10–15% of the time within Canada to support team collaboration, stakeholder engagement, and cross-site initiative.

Nice To Haves

Prior experience within the Canadian Healthcare ecosystem is considered a strong asset — familiarity with its regulatory landscape, stakeholders, and operational nuances will accelerate your impact in this role.

Responsibilities

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.