Permission to leap.

We are becoming stuck. Be it frustration or decision fatigue or insecurity or confusion — we are not moving forward at the pace of the competition, or our customer. And today is as good a day as any to change that.

Walmart leapt. If Walmart Connect — Partnership Marketing at the time — had simply grown with the market over the past seven years, that business would not have surpassed $900M yet. That's compared to its current annual run-rate of roughly $6BN.

It took a bet on a business unit that had stalled in growth for multiple years and said: "I will invest heavily in this business in hopes of turning it around." It paid off.

The playbook we built in June of 2018 for retail media is still applicable today for rest-of-market — seven years after the creation of Walmart's Supplier Advertising White Paper 1.0. At the time, the thesis was simple:

• If we do what everybody else is doing — follow the market.
• If we simply copy the Amazon playbook.

…we will not succeed.

But taking that approach required a tolerance for risk, the ability to encourage others to take risks, and scaled influence the likes of which are hard to come by now. It required someone to say, "the market is zagging, but I think we need to zig — trust me."

Retailers are struggling through perpetual change in market conditions, technology, consumer behaviors and more, and it's resulting in decision fatigue. There are simply too many things to focus on in this moment.

What it has meant for most retail media businesses is that we have entered "The Great Stall" where, similar to Walmart at the time, growth is stagnating. And what it has meant for the landscape to date is that most of us are still zagging — following the market, copying the same playbook without context, and reaching the same less-than-stellar outcomes.

In this week's Retail Media Leapfrog Series — a collection of thoughts designed to help retailers leapfrog incumbents by learning from the past — I realized that the things I've been writing to date should all have been prefaced with this post. I want to arm you with the confidence to leap.

Part No. 01The permission problem.

We are asking permission when we need to be stating the plan and following through. The nuance here is important, and I'll be the first to admit: I'm not good at this. Here's what we know:

• This is no longer optional. Retail media is a core tenet of retail strategy and growth moving forward. It is a competitive moat.
• You cannot wait. The economics of waiting are too costly — competitively, in opportunity lost, in future readiness.
• Retail media no longer grows on trees. If you aren't creating a competitive offering, you cannot be successful.
• You cannot scale with resources alone — you need technology investments. Normalizing inefficiency, burning out your teams, or accepting the status quo for the sake of skirting around technology investment is no longer acceptable.

The people in retail media see this. Most people in core retail don't. These articles are built for you to share internally — to help others see what you see.

But if you're in a place where you're fighting for resources against 'other strategic priorities', battling teams internally for dollars (is this truly incremental?), manually creating campaigns and measuring outcomes, or chasing shiny objects and 'immediate demand' — you likely haven't taken that leap yet.

Part No. 02Empowering decisions.

Stop asking permission. Empower your leaders with the information that will help them change. Again — nuanced. You could argue you've already done this. Has it worked? Because I've seen it work.

If you're leading retail media, your role is not just to make the case — it's to create the conditions for others to say yes and move with you. That means empowering your leaders internally to believe this is core to retail strategy, empowering your teams to work differently, and empowering the market to invest with confidence. Empowerment looks like:

• Leaders
  Walk your CFO through the IRR model. Don't just show revenue — show the 5-year return vs. investing in stores or supply chain. Show why the economics of waiting are negative, the comparable per-headcount costs, and the share of supplier marketing spend going to Amazon vs. your own category share.
• Teams
  Stop letting media operations sit on spreadsheets and email — believe them when they say "this is breaking." Build the business case and secure funding for workflow and automation so teams spend time selling and innovating, not copy-pasting campaigns.
• Merch & Marketing
  Bring them into the plan with clear JBP frameworks and incentives that align to their goals, not just yours. Propose shared incentives. Build an internal study with finance showing how joint go-to-market lifts all boats, reduces customer costs, and generates more sales.
• The Market
  Position retail media as a competitive moat in your earnings calls, investor decks, and brand summits. If you want advertisers to believe in your network, start by showing your own company does. Be bold, be loud.
• Own the Relationship
  Don't relegate sales, operations, or data to a network. Partners can and should play a role — in scale, activation, workflow. But the direct relationship with advertisers, agencies, and budgets has to be yours. That's where trust is built. That's where differentiation happens.

This is how you shift from 'retail media as an experiment' to 'retail media as a growth engine.' This is not a blind leap anymore — it's a calculated one, backed by 7+ years of proof and billions of dollars of growth.

Part No. 03Six pillars of the leap.

The 'leap' has evolved. At this point it's not about category creation or major investments in technology and resources — it's about convincing our organizations to plan and operate differently, invest differently, talk differently. And it's about rewiring our relationships with suppliers and their marketing and agency teams. To me, the pillars are:

01Tech unification & simplification of buying.

• Collapse complexity, integrate platforms, and make it easier for brands and agencies to spend.
• Tools built for your business — because your business is unique. It needn't be completely bespoke, but 'off-the-shelf' misses the intricacies of each retailer.
• Single workflow, fewer handoffs, automation where possible — and deeply understand current state before you make these moves.
• Prioritize efficiency and quality. Most expensive isn't always best; cheapest may not get you what you need. Relinquishing decisions to a procurement lead might not get the outcomes you desire.

02Sales & GTM simplification.

• Build hybrid teams that are easier to engage with internally and externally.
• Align incentives, pipeline management, stakeholder mapping, and a clean GTM strategy.
• Allow buying across multiple points of entry, but create incentives for a direct relationship — special access, insights, discounts, integrated planning, betas.

03Internal alignment: merch & marketing.

• Change management at scale: rewire how merch, marketing, and media work together — what Nick Hinsley calls "The Three Musketeers."
• Engagement models, JBP integration, education on the "why" and "how."
• Evolve incentive models to meet mutually beneficial growth — not just within media, but within merchandising and marketing too.

04Partner network: DSP & other.

• Rationalize the partner ecosystem — more does not equal more revenue; it equals confusion in the market.
• Architect incentives that don't cannibalize your own teams.
• Make external partnerships work for, not against, your strategy — this is a big one.
• Build fully transparent relationships — understand the media supply chain, total spends (pre-media, tech, other costs), and own the data, insights, and outcomes.

05Innovation offering.

• Create an innovation engine for what's next — but don't blindly follow every trend. Do what's right for your customer and your advertiser in that context.
• Prioritize innovation as a tertiary strategy to getting the foundation right. Otherwise teams get distracted by the shiny object.
• Create incentive tiers out of innovation programs.

06Supplier relationship rewiring.

• Shift from transactional negotiations to strategic co-investment focused on mutually beneficial growth.
• Engage brand marketing and agency teams directly, not just shopper — but respect shopper; they can help you.
• Agencies can help too, especially in understanding the needs of marketers investing national dollars.
• Build joint plans that tie retail media to business outcomes. JBPs have become too much of a 'forced ask' — get them back to mutually beneficial growth strategies, and align media and merchandising.

Be brave. Leap.

Easier said than done — I get it. Breaking out of the day-to-day and finding the conviction to leap is hard. But retail media is no longer a side project. It is not a test-and-learn. It is the next great growth engine of retail.

And the reality is this: the safe path isn't safe anymore. Following the market, copying the playbook, waiting for someone else to prove it out, hoping someone else will drive your revenues — those are the riskiest choices you can make.

This isn't about recklessness. It's about recognizing the moment we're in, owning the relationships that matter, and asserting the plan with confidence. You have more proof points today than Walmart did seven years ago. You have more tools, more market validation, more urgency from your customers and suppliers — and far better technology.

Be brave. Be confident. Empower. Leap. And if you want to read more, subscribe to the Retail Media Leapfrog Series.