Director, Technical Program Management

At Loblaw Digital, we know that our customers expect the best from us. Whether that means building the best, most innovative online shopping experience, or designing an app that will impact the lives of people across the country, we’re up for the challenge. From our office in Downtown Toronto, we’ve created leading eCommerce experiences in the online grocery shopping, beauty, pharmacy, and apparel spaces, and we’re only just getting started.

About the Role Our Director, Technical Program Management position is a people‑leader role that influences how we operate at Loblaw Digital. This role is accountable not only for owning a program portfolio, but also for shaping strategy, driving roadmap alignment, and enabling execution across a complex, multi‑domain environment. As a core member of a domain’s leadership team, you will play a key role in defining strategic direction and translating it into clear, actionable program plans.

Our TPM practice is deployed across multiple domains, businesses, and shared capabilities. We operate as a unit with a vision focused on bridging functions by making connections, inspiring transparency, communicating facts clearly, and enabling solution‑forward ideas collaboratively. As a Director within the practice, you will manage a portfolio that spans across domains, driving alignment with product, engineering, and business leadership. You will play a critical role in shaping domain strategy, influencing and aligning roadmaps, and negotiating priorities and delivery commitments with senior stakeholders across multiple groups. This role requires strong strategic thinking, executive communication, and the ability to balance long‑term vision with executional realities across large‑scale eCommerce and technology programs.

In addition, you will be responsible for building, managing, and growing a high‑performing TPM team. This includes developing people leaders and senior TPMs, establishing consistent standards for delivery excellence, and fostering a culture of collaboration, transparency, and continuous improvement.

What You Will Do

Serve as a key member of a domain leadership team, contributing to strategy definition and aligning business objectives with program execution

Own the domain program portfolio and shape roadmaps, driving clarity on priorities, sequencing, trade‑offs, and dependencies

Lead and develop a team of people managers and TPMs to drive end‑to‑end planning and delivery across domains

Drive and evolve the vision for technical delivery excellence, ensuring consistent, high‑quality execution across the portfolio

Partner with senior cross‑functional leaders to solve complex challenges, drive transformation, and deliver outcome‑based results

Negotiate, prioritize, and manage work with senior stakeholders across multiple groups, balancing strategic goals with execution realities

Sound Like You?

10+ years of experience building, scaling, and transforming program management functions, practices, and processes

Proven experience operating at a senior leader level as part of a leadership team, influencing strategy, roadmaps, and cross‑functional alignment

Demonstrated ownership of large, complex program portfolios spanning multiple domains and stakeholder groups

Proven people leader with experience leading leaders and building high‑performing teams

Strong strategic thinker with the ability to connect long‑term vision to execution; highly effective at influencing across all levels of the organization

Exceptional stakeholder management, executive communication, and technical acumen, with experience managing complex technical programs across diverse audiences

Strong technical ability with experience managing technical inclusive of communicating and managing technical constructs with varying stakeholders at senior levels of the organization

About Loblaw At Loblaw Digital, we seek great people to continually strengthen our culture. We believe great people model our values, are authentic, build trust and make connections. We’re able to keep innovating because our colleagues are passionate about their work and excited about the future of eCommerce. You will get to work with some of the best digital minds and will have support of world class technologies to help shape experiences our customers love!

Employment Type:

Full time

Type of Role:

Regular

Loblaw Digital recognizes Canada’s diversity as a source of national pride and strength. We have made it a priority to reflect our nation’s evolving diversity in the products we sell, the people we hire, and the culture we create in our organization. Accommodation is available upon request for applicants with disabilities in the recruitment and assessment process and when hired.

In addition, we believe that compliance with laws is about doing the right thing. Upholding the law is part of our Code of Conduct – it reinforces what our customers and stakeholders expect of us.

Hiring Range / Échelle salariale à l’embauche : $128,000.00 – $176,000.00 / 128.000,00$ – 176.000,00$ (per year / par an). A candidate’s experience and knowledge as well as the geographical region in which the position is located may be factored into the pay a candidate receives for this position. This posting is for an existing vacancy. The company uses artificial intelligence for the purpose of screening, assessing and/or selecting applicants for this position.

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