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What’s up folks, today we have the pleasure of sitting down with Megan Kwon, Director, Digital Customer Communications at Loblaw Digital.

Summary: Orchestrating multi-channel messaging for 1 brand and product is tough. But imagine doing that across dozens of brands and thousands of products. Megan leads digital customer communications at Loblaw Digital, turning enterprise-scale messaging into something that feels personal. She built her teams around the customer journey, giving each pod full creative and data ownership. The people driving results also own the tools, learning by building and celebrating small wins. Her “change champions” make new ideas stick, and her view on AI is grounded; use it to go faster, not think for you. Curiosity, she says, is what keeps marketing human.

In this Episode…

• Customer Journey Pods and Martech Team Structures
• How to Assign Martech Tool Ownership and Drive Real Adoption
• Why Change Champions Work in Martech Transformation
• How To Manage Transactional Messaging Across Multiple Brands
• Why Shared Ownership Improves Transactional Messaging
• Why Human Governance Still Matters in AI Messaging
• Why Curiosity Matters in Adapting to AI

About Megan

Megan Kwon runs digital customer communications at Loblaw Digital, the team behind how millions of Canadians hear from brands like Loblaws, Shoppers Drug Mart, and President’s Choice. She’s part strategist, part systems thinker, and fully obsessed with how data can make marketing feel more human, not less.

Before returning to Loblaw, Megan helped reshape how people discover and trust local marketplaces at Kijiji, and before that, she built growth engines in the fintech world at NorthOne. Her career has been a study in scale; from scrappy e-commerce tests to national lifecycle programs that touch nearly every Canadian household. What sets her apart is the way she leads: with deep curiosity, radical ownership, and a bias for collaboration. She believes numbers tell stories, and that the best marketing teams build movements around insight, empathy, and accountability.

Building a Career Around Conversations That Scale

Running digital messaging at Loblaw means coordinating communication at a scale that few marketers ever experience. Megan oversees the systems that deliver millions of emails and texts across brands Canadians interact with daily, including Loblaws, Shoppers Drug Mart, and President’s Choice. Her team manages both marketing and transactional messages, making sure each one aligns with a specific stage in the customer journey. The workload is immense. Each division has its own priorities, and every campaign needs to fit within a shared infrastructure that still feels personal to the customer.

“We work with a lot of different business divisions across the entire organization. Our job is to make sure their strategies and programs come to life through the customer lifecycle.”

Megan’s team operates more like a connective tissue than a broadcast engine. They bridge the gaps between marketing, product, and data teams, translating disconnected strategies into a unified experience. That work involves building systems capable of:

• Managing multiple brand voices while keeping messaging consistent
• Triggering real-time communications that respond to customer behavior
• Integrating old and new technologies without breaking operational flow

Every campaign becomes part of a continuous conversation with the customer. Each message is one step in a long dialogue, not a one-off announcement.

Megan’s perspective comes from experience earned in very different industries. She began her career at Loblaw during the early days of online grocery, a time when digital operations were experimental and resourceful. She later worked across fintech, marketplaces, and paid media before returning to Loblaw. That journey helped her understand every layer of the customer funnel, from acquisition through retention. It also taught her how to combine growth marketing tactics with enterprise-level communication systems, that way she can scale personalization without losing humanity.

Most large organizations still treat messaging as a collection of isolated programs. Megan treats it as an ecosystem. Her work shows that when lifecycle and acquisition efforts operate within a shared framework, communication becomes more coherent and far more effective. Alignment between data, channels, and teams reduces noise and builds trust with customers who engage across multiple brands.

Key takeaway: Building a unified messaging ecosystem starts with structure, not volume. Create systems that connect channels, data, and brand voices into one coordinated experience. Treat messaging as a relationship that continues long after the first conversion. That way you can make enterprise-scale communication feel personal, intentional, and consistent across every touchpoint.

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Customer Journey Pods and Martech Team Structures

Running digital communications at Loblaw means managing one of the largest customer ecosystems in the country. The team sends millions of messages across grocery, pharmacy, and e-commerce brands every week. Each interaction has to feel personal, relevant, and timely, even when it comes from a massive organization. Megan explains that the only way to handle that kind of scale is to treat data as the operating system and collaboration as the backbone.

Her team relies on analytics to shape every message. Real-time signals from dozens of digital properties guide what customers see, when they see it, and how those experiences evolve. It is a constant feedback loop between behavior and communication.

“We lean a lot into the data that we gather,” Megan says. “That pretty much drives almost everything that we do.” The systems are only half the story, though. The other half is how her team stays connected across offices, divisions, and projects.

They share knowledge in Coda, manage progress in Jira, and rely on Slack to keep conversations fluid. Even their emojis have purpose, creating a shared language that makes collaboration faster and more human.

“Everything that we do, we share that knowledge back and forth so that we can continue to learn off each other,” Megan said.

The team structure used to follow the company’s business units. Each division had its own specialists who acted like small internal agencies. It worked for speed, but it made collaboration harder. Megan reorganized everything around the customer journey instead. Her teams now work in “pods” that align with stages such as onboarding, discovery, shopping, and post-purchase. Each pod has both data and creative ownership over its domain. That way, a single team can experiment, learn, and apply what works across multiple brands.

Megan also built intentional overlap between pods to keep ideas moving. For example, the loyalty and early engagement pod owns both new-member activation and retention. That connection helps them understand the full customer arc, from first purchase to repeat visits. The result is a flexible structure that shares expertise fluidly without losing focus. Large enterprises tend to slow down under their own weight, but this model keeps Loblaw’s marketing engine fast, synchronized, and grounded in customer behavior.

The work Megan’s team does might look complex from the outside, but its principle is simple. Organize around how customers move, not how departments are charted. Measure everything, talk constantly, and design your structure for learning, not hierarchy.

Key takeaway: Build pods around the customer journey, and give each one shared data, clear ownership, and the ability to collaborate without friction. That way you can remove silos and increase creative velocity at the same time. When every team sees the same customer signals and shares the same goals, the organization starts acting like a single, adaptive system rather than a collection of departments.

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How to Assign Martech Tool Ownership and Drive Real Adoption

Martech ownership often turns into a quiet tug-of-war. Procurement wants a seat at the table, IT guards permissions, and marketing operations gets stuck in the middle when the system fails. Megan skips the politics entirely. Her team at Loblaw Digital owns the messaging stack end to end because they are the ones responsible for sending communications, managing data flows, and driving measurable customer outcomes. Ownership, in her words, “always comes down to the team driving the value.”

“We are the ultimate accountability party for platforms around messaging,” Megan says. “That includes how we use it, how we govern it, and whether we’re actually getting the most out of it.”

In practice, that means her team handles everything from tool configuration to deployment governance. They decide how the system should operate, not just what it should do. This structure eliminates the ambiguity that plagues many enterprises where one group signs the contract, another handles technical setup, and a third is expected to prove ROI. By anchoring ownership in the team that directly moves the levers of value, Megan ensures every message, automation, and experiment has a clear line of accountability.

The harder challenge, she admits, is adoption. Tools fail when they’re introduced as theory rather than practice. Megan has seen enough rollouts to know that “new platforms are always 50/50, either wildly successful or barely used.” To shift those odds, she attaches every onboarding to something tangible. No generic enablement sessions or “click-through” tutorials. Each new tool is tied to a live initiative, whether that’s a transactional campaign, an internal process improvement, or a customer-facing launch. The team learns by building something real.

She describes it as “learning with your hands on the steering wheel.” Every project begins with a defined use case before the tool is even purchased. Training then becomes an exercise in momentum, not memorization. Her team builds small habits early (checking analytics daily, logging feedback, or reviewing campaign performance weekly) so that use becomes second nature. Those rituals create long-term retention more effectively than any manual or course could.

“I think of it in daily habit terms,” Megan says. “Once we’ve identified the use case, we make sure there’s no friction. We do check-ins, celebrate outcomes, even tiny milestones. Those moments build emotional validation that the tool is working and worth the effort.”

The celebration component might sound small, but it changes the emotional tone of adoption. Her team uses internal channels and in-person acknowledgment to recognize progress quickly. When someone builds a new automation or solves a delivery issue, that win gets shared immediately. Over time, that steady reinforcement builds a positive feedback loop. Tools become something people want to use because they associate them with progress, collaboration, and visible achievement.

Key takeaway: Give martech ownership to the team that actually drives value, not the one holding the budget. Tie every martech rollout to a visible business outcome and celebrate quick wins. That way you transform tools from passive assets into active systems of progress, and your teams learn by building, not by watching.

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Why Change Champions Work in Martech Transformation

Change inside large marketing organizations rarely fails because of technology. It fails because of people. Megan has seen it too many times: teams want progress but dread disruption. When a new platform or workflow shows up, anxiety follows. Her solution is to identify and empower “change champions,” trusted peers who can translate confusion into confidence.

“Even when it’s a really exciting change, there’s a lot of anxiety around it,” Megan said. “I look for people who have a bit more open-mindedness to it, people who can see the opportunity before the friction.”

Her process starts with careful selection. She looks for people who are curious, grounded, and respected by their peers. Titles do not matter as much as temperament. She then gives them what they need to go deep: time to explore, space to learn, and access to training that prepares them to lead informally. These champions act as the first to test new tools, ask the awkward questions, and share early wins with the rest of the team.

Peer influence carries more weight than corporate messaging. Megan believes that reassurance from a colleague is far more persuasive than reassurance from leadership. That is why she embeds champions directly in operating teams. They create an informal feedback loop where questions get answered quickly and small frustrations get solved before they spread. When change feels personal and local, adoption follows naturally.

She shared one story that captures this idea. Her team needed to start connecting marketing results to financial outcomes through new business reviews. Rather than dictate a process, she asked a few team members to shape it themselves. They experimented, iterated, and presented their version to leadership. Over time, those sessions became routine, and leadership praised the transparency and clarity. The team now owns the process entirely and sees it as a shared win, not a top-down mandate.

Change champions are a multiplier. They lower friction, increase buy-in, and create a sense of ownership that training programs rarely achieve. Every transformation that lasts comes from people who model what adoption looks like in the real world.

Key takeaway: Start every transformation by finding a few natural early believers. Give them real time, trust, and visibility. Let them lead experimentation and share their discoveries with peers. Change spreads fastest when it moves through relationships, not announcements.

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How To Manage Transactional Messaging Across Multiple Brands

Coordinating transactional messages across an enterprise as sprawling as Loblaw is like conducting an orchestra where every instrument plays a different genre. Megan handles millions of automated communications each year across grocery, pharmacy, and loyalty brands that share customers but operate with different tones, cadences, and tech stacks. Every push notification, SMS, and email must land at the right time, through the right channel, without stepping on another message from a sibling brand. The complexity is staggering, but the philosophy is simple: intentional orchestration beats volume every time.

“We spend a lot of time thinking about how often a customer hears from us,” Megan says. “Each brand has its own voice, and customers might hear from several of them in a single day. The work is about deciding what they should hear first.”

Her team treats transactional communication as a living system, not a set of automated triggers. They factor in urgency, relevance, and context before deployment. A grocery order confirmation should arrive instantly. A pharmacy reminder might need a delay if the system detects another message is already en route. And if the data shows that a customer has ignored push notifications for weeks, the system temporarily silences that channel instead of blasting more noise. That way you can protect trust and preserve signal quality across the network.

Governance is where the invisible work happens. Weekly prioritization meetings, data-backed deployment calendars, and staggered rollout plans ensure coordination across business units. The team uses analytics not only to track opens and clicks but to gauge “channel health.” If engagement rates dip, Megan’s group takes a pause rather than pushing through. When metrics recover, they resume with better timing and smarter segmentation. It is part science, part intuition—an ongoing calibration between technology and empathy.

When priorities clash, which they often do, human judgment becomes the final control layer. Grocery might need to notify about an order pickup at the same time the loyalty team wants to celebrate bonus points. In those moments, Megan’s team decides what matters most to the customer’s day, not just to the business’s calendar. The result is a system that favors the human on the other end of the message rather than the automation that delivers it.

Key takeaway: Treat transactional messaging like a living ecosystem, not a queue. Build governance upstream so that urgency, frequency, and relevance are considered before deployment. Use data to monitor channel health and pause when fatigue appears. Prioritize human judgment at the point of conflict. That way you can maintain trust and clarity across every brand voice that shares your customer’s inbox.

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Why Shared Ownership Improves Transactional Messaging

Transactional messages often reveal how a company really operates. They sit at the intersection of product, engineering, and marketing, quietly exposing every communication gap and ownership flaw inside the business. Most teams treat them as a technical necessity instead of a customer touchpoint, which is why they often get lost in backend code and forgotten metrics. When ownership is unclear, no one tracks performance, brand consistency fades, and the customer experience becomes fragmented.

Megan’s team at Loblaw Digital restructured this process with precision. They built a co-ownership model that connects product, development, and digital communications, creating constant collaboration instead of isolated ownership.

“We built interdependency by design,” Megan said. “It means we’re always asking if we should send something, what to say, and how to say it.” That model makes every message a conscious decision. It forces teams to think through intent, timing, and tone before anything reaches the customer.

Her team operates with practical interlocks instead of vague handoffs. Each transactional message moves through a sequence that includes:

1. Evaluating whether the event requires communication.
2. Aligning on the right moment and tone for the customer.
3. Confirming data flow and delivery reliability.
4. Reviewing the brand consistency across templates.

This rhythm ensures messages are relevant, accurate, and aligned with customer expectations. The process feels more like product development than marketing, which is exactly the point.

Megan’s biggest lesson is that context saves time. Teams waste hours correcting mistakes that could have been avoided through early discussion. “Spending the time upfront saves time down the line,” she said.

Clear context reduces rework, keeps messages aligned with brand purpose, and strengthens collaboration. When each group has clear accountability and visibility, you get fewer silos and better execution.

Key takeaway: Treat transactional messaging as a shared operational system. Design interdependencies across product, development, and marketing so that every message reflects intentional choices. Invest time upfront to build shared context, because alignment in the beginning eliminates chaos later and turns required communications into meaningful customer moments.

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Why Human Governance Still Matters in AI Messaging

The fantasy of machine-led marketing automation keeps resurfacing in boardrooms. People picture a system that quietly decides when to launch campaigns, which audiences to target, and what creative to serve, all while the humans nod in approval. Megan hears that idea often, and she treats it with both respect and skepticism. AI has changed what is possible in customer communications, but it has not replaced the need for discernment.

“AI is a driver of volume and speed,” Megan says. “But innovation still starts with human instigation.”

She sees AI as a production multiplier, not a strategist. Her team uses it to increase output, test ideas faster, and explore variations that would have taken weeks to build manually. Yet the spark that defines a strong message still comes from a person who understands timing, emotion, and context. Megan knows that AI can fill the pipeline with options, but only humans can decide which ones deserve attention. That judgment remains the heartbeat of marketing.

Governance has become the underrated topic in all of this. Speed attracts headlines, but control determines survival. Teams often experiment with AI before they establish clear standards for brand tone, accuracy, or ethical boundaries. Megan believes that governance is not bureaucracy; it is infrastructure. It protects creativity from chaos. In her view, a responsible AI system should scale both productivity and accountability, with governance acting as the connective tissue between the two.

Her team’s workflow mirrors that belief. They use AI to brainstorm and generate, then human review to curate and approve. The pattern looks simple, but it requires discipline.

• AI drafts and predicts; humans direct and refine.
• Governance enforces rules that prevent automation from drifting.
• Review cycles move quickly, but every output still reflects brand values.

Megan calls AI a “partner in crime,” a phrase that captures both her humor and her pragmatism. Her optimism does not come from believing AI will do the work for her. It comes from watching her team learn how to harness it responsibly, using its speed to unlock better work without losing control of the message.

Key takeaway: AI produces output faster than any human ever could, but only human governance can protect meaning, quality, and ethics. Use AI to accelerate what you already do well. Build lightweight rules that preserve judgment while multiplying speed. That way you can scale creative impact without surrendering control.

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Why Curiosity Matters in Adapting to AI

AI hype moves faster than reality. On social feeds, every new update sounds like a revolution. Inside real companies, transformation crawls. Enterprise systems take years to shift, and most people are still learning to write a good prompt. Megan’s advice for anyone feeling behind is simple: relax and stay curious. Fear burns energy. Curiosity builds capability.

She keeps her “just chill” mindset close. It is not about denial. It is about perspective. Every wave of innovation since the late 1990s has looked world-ending at first: ecommerce, automation, social media, personalization. None eliminated the need for humans who think critically and connect dots.

“Spend time just hanging out with ChatGPT and see what happens,” Megan says. “Not in a passive way, but by asking real questions and testing what it can do.” Curiosity turns AI from an abstract threat into something concrete you can experiment with.

Megan believes engagement should start small and personal. Try something that interests you. Ask questions about problems you already face at work. Observe what it gets right, what feels off, and what makes you want to dig deeper. Then share that feedback. “If you’re not enjoying something or you’re curious about something, share that feedback,” she says. “That’s how we keep driving it forward.” She sees feedback as the missing ingredient in most enterprise AI rollouts. Experimentation without conversation stalls progress.

The part that stands out most in her perspective is how she talks about creativity. Megan wonders whether AI can ever experience that strange spark that hits when you least expect it: during a commute, a shower, or a half-distracted chat with a colleague. That moment of randomness (the human brain forming a new connection) still drives the best marketing ideas. Tools can predict patterns, but sparks like that shape culture.

Key takeaway: Curiosity outperforms anxiety in any era of change. Spend time experimenting with AI tools, test them with specific questions, and share what you learn. That way you can build confidence through direct experience instead of secondhand fear. The people who stay curious and keep contributing human feedback will shape how AI actually works in practice.

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Creating Sustainable Energy in Marketing Leadership

Ambition is a double-edged tool. It builds careers, but it also builds pressure. Many leaders spend their early years obsessed with the next milestone, chasing every possible way to accelerate growth. Megan has lived that tension and learned how to disarm it. She now measures progress through presence instead of pace.

Her perspective shifted when she realized that trying to predict every step of a long career only makes the journey heavier. The more she planned, the less she enjoyed the work itself. She began focusing on the moments that actually energize her; the meetings that spark new ideas, the mentoring conversations that build confidence in others, the feeling of momentum when a project starts to click. Those are the pieces that make a career feel alive.

“My happiness is really just enjoying what I’m doing, looking ahead every so often, but really just enjoying what I’m doing and making the most of it.”

Megan protects her energy like a resource. She walks away from her desk at defined points in the day. She prioritizes time outside, whether that means working on her golf swing or biking through a local trail. These pauses are not indulgences. They are maintenance. Every marketer who runs on adrenaline eventually learns that creativity needs recovery time. Stepping away resets attention and keeps your work sharper when you return.

Her extroversion fuels her leadership. She channels her natural energy into connection, and when the snow comes, she redirects that drive toward snowboarding and skiing. Physical outlets turn her intensity into clarity. Many people treat balance as an abstract ideal, but Megan treats it like a system. She builds it into her week, tracks it through her routines, and treats it as a form of long-term performance management.

Key takeaway: Long-term ambition only works when energy is renewable. Protect your attention with real boundaries, invest in physical outlets that refresh your focus, and let presence (not pressure) define your pace. That way you can stay creative and engaged over the long arc of a marketing career.

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Episode Recap

Megan runs digital customer communications at Loblaw Digital, shaping how millions of Canadians hear from Loblaws, Shoppers Drug Mart, and President’s Choice. Her team manages both marketing and transactional messages, each message is part of a continuous dialogue, not a one-time campaign blast. Data drives timing and tone, but human judgment shapes what actually gets sent. “Each brand has its own personality,” she says. “Customers might hear from several of them in a single day. The work is about deciding what they should hear first.”

Megan rebuilt her team around the customer journey instead of departments. Each pod owns a stage (onboarding, shopping, retention) and includes both creative and data ownership. The setup keeps experiments fast and collaboration natural. Large organizations tend to slow down under process, but her structure makes movement the default.

Tool ownership follows the same principle. The people driving results control the tech. Every platform rollout ties to a live initiative, teams learn by doing and celebrate quick wins to build momentum. “Once we’ve identified the use case, we make sure there’s no friction,” she says. “Those moments build emotional validation that the tool is worth the effort.” When she leads change, she finds “champions” inside teams; people curious enough to test first and share results. They lower friction, turn confusion into progress, and make adoption contagious.

AI fits into her system as a multiplier, not a replacement. It boosts output, but humans keep control through governance and creative review. She calls AI a “partner in crime,” useful only when you stay in the driver’s seat. Her advice for marketers watching the AI hype is simple: stay curious. Experiment, ask better questions, and treat new tools as something to learn with, not to fear. Curiosity builds confidence faster than any rollout plan.

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Intro music by Wowa via Unminus
Cover art created with Midjourney (check out how)

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