The murky middle: Why off-site is retail media’s real test

I’ve always loved the murky middle.

The Two Towers is my favorite entry in Tolkien’s The Lord of the Rings. Harry Potter and the Order of the Phoenix is my top pick in that series. And The Godfather Part II is better than Part I, and the best of the trilogy.

That preference for the messy middle also shows up in my work life too. If the situation is a little unclear, a little chaotic — perfect! That’s when I roll up my sleeves and dive in.

Right now, that’s where we are in commerce and retail media. We’re out of the honeymoon phase. We’ve collectively done the work of launching. Now we’re at a critical juncture, asking, Where do we go next?

The easy answer is “off-site.” And yes, I’ve bet my career on it and my LinkedIn posts make my advocacy clear. But the reality is more nuanced than that. According to EMarketer off-site retail media ad spend is expected to grow at two times the rate of on-site through 2026. Why? For two clear reasons.

1. On-site supply is finite. While on-site media generally drives strong margins, there’s only so much digital shelf space — and most retailers don’t have even close to the 3 billion site visits Amazon receives per month.
2. Retail media networks (RMNs) need to grow. The pressure is on to diversify revenue. That means extending into new channels. Off-site is an obvious next step as it allows retailers to activate their valuable first-party data, offer closed-loop measurement and do it all at scale.

But here’s the catch. Not all RMNs are equipped to pull this off. We’re starting to see a split between those who are evolving off-site and those who aren’t.

The winning RMNs share three traits:

• They have a clear value proposition tied to their overarching retail brand.
• They have internal teams who understand how to sell programmatic media.
• They have unique offerings that create demand and drive repeat investment.

When I was at the Kellogg School of Management, I took a class with Professor Tim Calkins. His frameworks are still the most valuable tools I’ve carried into my career. (Sorry to my direct reports, who now have them memorized too.) The lessons around vision and brand position feel tailor-made for retail media today.

Your vision is your North Star — where you are headed.

Your brand position is your audience. And it can’t be everyone with a media budget.

Too many RMNs operate with entitlement: “I’m a big retailer. Of course, advertisers will buy from me.” And sure, they’ll buy your on-site because that’s exclusive inventory. But your off-site? They could probably cobble together your audiences elsewhere — so make it matter to them.

One RMN doing really well is Dollar General Retail Media Network. Their pitch is simple, sharp and defensible. “Rural Americans are hard to target. We can reach them.” That’s a proposition that sticks. But more importantly, they back it up with activation — through curated inventory, relevant audience insights and messaging that resonates with their shoppers’ behaviors and preferences. It’s not just media — it’s media that matters.

Another gap I’m seeing is education. I get it. Programmatic sounds complicated. Social media is easy — everyone uses it. But if we define “programmatic” in more human terms, it gets a whole lot simpler. Here’s what programmatic really is:

• The ad in your favorite podcast
• The spot that plays before the new episode of The Bear on Hulu
• The banner ad halfway through your Wall Street Journal article
  

That’s off-site. That is the open internet. When sellers get that, they get better at selling it.

Of course, I wouldn’t be Claire Wyatt if I didn’t talk about measurement.

Closed-loop measurement is one of retail media’s foundational promises. But let’s go further. We need unique and specialized measurement solutions — and I don’t just mean incrementality — to draw advertisers back to you time and time again. Providing insights about customer behavior unique to your business can help you continue to drive growth and stickiness.

Kroger Precision Marketing leads the pack here. Pulling together Kroger’s consumer insights, loyalty marketing and retail media businesses into one team under the leadership of Christine Foster was a brilliant move. They know exactly how to drive long-term value. It’s not just about monetizing ad placement — it’s about monetizing intelligence.

I’m retail media’s biggest cheerleader. I want this little corner of the advertising market to succeed. But, to bring it back to The Lord of the Rings, we’re stuck in Helm’s Deep — that grim fortress from The Two Towers, where the heroes are surrounded and outnumbered, hoping reinforcements arrive soon.

To break out, we need retail media leaders who can think strategically, not just tactically. We need teams who know how to sell value, not just impressions. We need bold moves, smarter measurement and clearer messaging. In short: we need our own retail media versions of Aragorn — the kind of leader who can rally scattered forces, inspire belief against long odds and turn the tide when it matters most. (For fellow Tolkien fans, this needs no explanation.)

This op-ed represents the views and opinions of the author and not of The Current, a division of The Trade Desk, or The Trade Desk. The appearance of the op-ed on The Current does not constitute an endorsement by The Current or The Trade Desk.