The ‘why and how’ of [technical] program management

Matt Dudman
Loblaw Digital
Published in
7 min readApr 10, 2024

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Interested in a program management role at Loblaw Digital? This article provides a snapshot overview of the Program and Technical Program Management practice at

(LD); it outlines the high-level functional influence and responsibilities, how we operate, as well as how we approach the build and growth of our practice.

Why [Technical] Program Management at Loblaw Digital

The program management practice at LD has grown and scaled with purpose over the last several years by vertical, people, impact and value. Though traditional project/program management can often be misconstrued as solely a support function, the roles at LD are a critical component within our technology organization and across our larger digital division, bridging and articulating at both strategic (ie. orchestrating) and tactical levels (ie. executional planning).

Our program practice operates at the fulcrum point of our cross-functional teams — across engineering, product, design, and the business (to name a few). The ability to effectively manage and bridge alongside these teams is how we succeed, and ultimately is our secret sauce. We live and breathe the concept of orchestration, contextualization, and forecasting. We assemble cross-functional experts. We drive partnership with our businesses. We bring clarity to chaos. We drive outcomes.

Our Roles

The program practice is responsible for leading, facilitating, and enabling specific initiatives that need an extra level of leadership and management — think those ‘big bets’ that cross-functionally, an extra set of eyes and foresight goes a long way!

Program & Technical Program Management drive planning and communication management across our largest prioritized initiatives that span across our businesses, verticals, domains, and services. Program partners with cross-functional experts to orchestrate and lead one view and one plan while ensuring clarity & transparency into challenges, realities, and progress towards outcomes.

We have two practice roles that work closely and collaboratively together:

  • Program Management: Focus on leading large, cross-vertical, strategic initiatives where colleagues are fluid and move between prioritized initiatives based on organizational needs.
  • Technical Program Management (TPM): Focus on driving vertical-specific technical programs where colleagues are dedicated to a specific business/capability for programs that span across initiatives, domains, and core-services.

The net net: we lead, facilitate, enable; and the team can’t wait to partner!

How we operate

As orchestrators, we’re accountable for bridging and leading teams with a focus on orchestrating technical delivery excellence. The below outlines a few high-level attributes of the program practice as well as core areas of influence.

  • Lead. Facilitate. Enable. As leaders of orchestration, think of the following as the core pillars of ‘what we do’: lead end-to-end plan management, drive communication and source of truth, and partner with teams to identify and manage risks/dependencies and drive accountability.
  • Clarity through communication. Think of the following as the ‘why we do’: we bridge gaps between functional mandates; we own the components that make up a plan; and we drive accountability, next actions, and outcomes.
  • Bring people and teams together. Think of the following as the ‘how we do’: partner and collaborate with product, technology, business, and cross-functional partners; manage program ‘total picture’ management by ensuring cross functional teams come together in efforts of understanding specific initiative goals, objectives and path to delivery; and enable and foster relationship management, stakeholder communication, and management of cross team dependencies.

The result is clarity on the big picture and a source of truth of how our initiatives and technical programs are evolving and progressing towards our goals.

What the role ‘is not’

Program manager roles differ by organization, similar to the core mandates of specific roles, and the ‘what’ (hard skills) and the ‘how’ (soft skills) all contribute to successful candidates. At LD, we believe that the functional expertise (and those with the necessary skills and experience) have significantly more to offer than the traditional lens. We believe:

  • The role is not just a support function. The role is an integrated pillar that is closely partnered among our engineering, product, design, and business teams.
  • The responsibility of the role is not solely booking meetings and taking notes. Arguably everyone does this at some point, but it is not part of the foundational mandate.
  • The role responsibility is not solely about scope, timeline, resources, and budget. Our teams at LD are empowered to provide solutions and operate in an influential manner, feel encouraged and drive ideation through collaboration.

Ultimately, we want you to share your ideas, embrace your leadership, and harness your expertise and drive because we recognize the unique value this role, and the people in it, have on the organization.

How we ‘build & grow’ our practice

Hiring and building a team is one thing, developing and sustaining the team is another…but in many cases they work hand-in-hand and require the commitment and dedication of the entire team to be successful. From developing and aligning on a strategic and common vision and setting clear goals, to executing week-over-week with our peers and throughout the organization, all colleagues within the practice play a role in both individual and practice success…ultimately impacting positive experiences across teams, businesses, and our customers.

Building our teams

We’ve been fortunate to have continued growth over the years: adding new verticals, assessing and evolving the makeup of our practice, shifting role mandates, introducing new methodologies of adding value, and continuously scaling to provide organizational impact.

When a candidate applies for a role, our team considers all open roles within our practice. The process is inclusive of elements like:

  • Skills and experience being assessed against our open roles so we can determine where a candidate may best be set up for success (while considering the direct application).
  • Partnering closely with our talent acquisition team to engage with the candidate and manage expectations for interview management (outlining expectations of each step).
  • Providing an equitable candidate experience — from clarity on the process and diverse interview panels through to clarity on next steps and decisions.

Once a candidate has been hired, what happens next? It’s time to onboard. We have a three-tier system for onboarding in our practice that loosely outlines to the following:

  • Organizational onboarding. Our LD-HR team leads sessions closely partnered with functional experts to give you the latest and greatest on the organization!
  • Functional/role onboarding. Welcome to the program practice! You will have a personalized document that outlines expectations, access to documentation to review, who you should meet with, and how you’ll progress against goals you set with your manager over the first few months.
  • Vertical/Business onboarding. As part of the above and depending on where you’re allocated, it’s important that you get up to speed on the area of which you’ll be working (a particular business, a capability, our platform, etc.) Context is crucial at the end of the day so we believe it’s important for us to provide you with the insights that will help you learn quickly, and effectively!

Growing our teams

The cycle of growth varies by individual, and by individual aspirations. Growth can mean something different to everyone, and in some cases, people limit themselves to only consider role-based growth, when in reality, it’s so much more. In many cases, we’ve found that varying colleague aspirations coupled with individual growth and development paths are the building blocks that prepare and organically elevate a colleague to the next promotional level.

Growth opportunities come in many shapes and sizes, and we coach our team members to consider all of them as they progress through their time at LD: from inter-vertical experience (ie. working on FE, BE, Mobile, or specific types of initiatives), to industry experience (ie. working in loyalty, healthcare, media, grocery, etc), to scaling individual aspirations (ie. individual contributor to a people leader, promotional growth, involvement in culture, operating among senior leaders, etc.). The easiest way to work towards growth is to start by establishing an understanding of what you’re looking to achieve!

These types of opportunities start by acknowledging and establishing an understanding of what you’re looking to accomplish and translating these ideas and reflections into a comprehensive growth and development plan. Following this, having an open and honest two-way conversation with one’s manager is always recommended — ideate together, partner, work through aspirations, and ensure aspects of this plan are clearly articulated in both performance goals and individual development plans.

We believe that everyone has the opportunity to grow; and growth means something different to everyone!

Interested, or curious?

There are job opportunities and the program and technical program management roles are crucial to our success. We’re passionate about building best in class digital experiences, driving outcomes that impact millions of Canadians daily, and striving to innovate, accelerate, and operate in a manner that helps both our colleagues and customers live life well.

If you’re interested in taking the next step in your career, or looking to broaden your experience, we’re hiring: Loblaw Digital Program Practice roles.

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