4 Brand-Side Retail Media Leaders Share Risky Bets That Paid Off
The key isn't being reckless—it's being willing to challenge conventional wisdom when the opportunity presents itself.
In retail media, playing it safe might feel comfortable, but the biggest wins often come from the biggest swings. Today, I'm diving into those heart-stopping moments when retail media leaders threw caution to the wind and bet big on unproven strategies.
One brand gambled their entire brand anniversary budget on the world's largest box of chocolates and earned 750 million impressions. Another leader intentionally diversified away from their 'hero' keyword that was driving most results, and another who made the bold call to go completely dark during peak shopping hours.
If you've ever wondered whether that big, scary idea is worth pursuing, this episode might just give you the courage to take the leap.
Trading Paid Media for a World Record
Josh Clarkson, Global Lead for Retail Media at Mars and Chief Consultant at Edify Digital Commerce Consulting, faced a classic retail media dilemma: how to make a modest budget work for a major milestone.
"I used to work for a business in the US called Russell Stover. It's a chocolate business owned by Lindt. We didn't have a huge amount of budget for paid media activations when we were turning a hundred years old, two years ago," Josh says.
Instead of spreading their limited budget across traditional paid channels, Josh's team made a bold pivot. "We took a huge risk and we sunk our paid media budget into getting the Guinness World Record title for the world's largest box of chocolates."
The gamble paid off spectacularly. "That activity, that event, garnered 750 million earned and shared impressions at a CPM we never could have acquired through paid channels," Josh says. "We really went after other parts of kind of owned and shared rather than the paid piece. It was a huge success and also a really proud moment for the team."
Betting Big on an Unproven Color
Todd Weagant, Director of Sales at Massimo, took a different kind of risk—one that required trusting his gut on consumer preferences before any data existed to support it.
"For Amazon, doing a bold, exclusive color that was not necessarily proven as a color at the time. So it was a certain color that magically a cell phone manufacturer came out with that same color after we took the chance on the headphone color," Todd says.
The decision came down to a simple but nerve-wracking moment: "The chance was literally taking the buyer or vendor manager at Amazon and saying, do you like this color? 'Cause we're gonna take a big bet on it."
Todd's team collaborated with Amazon and worked it out, but as he admits, "it was a total luck of the draw." That luck, combined with bold decision-making, resulted in "one of the bestselling headphones in Amazon history."
I hear it all the time, ”How do we get more from our retail media spend?” Well, here’s the truth: if your retail and digital teams are still doing their own thing, you’re probably leaving real money on the table.
Shoppers don’t think in silos—they bounce between online and in-store without skipping a beat. Acosta Group’s Connected Commerce agency helps brands unify trade and retail media budgets to invest where shoppers are most likely to convert —whether that's on mobile or in the store aisle. Learn more about Acosta Group Connected Commerce at Acosta.Group
Going Dark During Peak Hours
Neha Gupta Malik, Head of Connected Commerce at Mizkan America (parent company of CPG brands including Ragu, Barilla, and Holland House), shared how aggressive testing can mean literally disappearing from search results.
"At Mizkan we're very big on test and learns, and we do them often," Neha says. Her team recently pushed the boundaries with search dayparting experiments on Walmart. "We've recently, in the last three months, gone very aggressive with some of the way we optimize, the way we pause for certain hours or we enhance for other hours."
The stakes? "We were non-existent as a brand from a brand saliency for a period of time. So that was a huge risk," Neha says. "Of course, we all know search as we know it's the online aisle, so to not be there obviously poses a big risk."
Despite the danger of going dark during certain hours, the evaluation showed it was the right move. The learnings have been so valuable that Neha's team is now planning to test with other retailers.
Neha also shared another major risk her team took with CTV advertising. "One of the biggest things is because of the investment levels, because we obviously, anytime you're going to carve out a dollar to spend somewhere, it's a dollar away from one of the other tactics that might have been proven," she says. "It's not like we have endless budgets. So to be able to make some of those critical decisions within your media... obviously it's coming from somewhere. So that was the biggest risk to be mindful of."
Abandoning the Hero Keyword
Chris Lowrey, Brand Director at Our Home (parent of CPG brands including Pop Secret, Good Health, and Popchips), discovered that sometimes the biggest risk is diversifying away from what's working.
Chris's team was facing a crisis: "We were flatlining on sales and our ROAS was dipping." After digging into their keyword performance, they made a shocking discovery. "More than 95% of our manual sales were coming from just one keyword."
Rather than playing it safe with their hero keyword, Chris's team made a bold move: "It was a huge red flag where we just pulled the ripcord and took a leap and aggressively shifted our budget away from the safety of that single keyword and redistributed spend across new ones."
The payoff? "It made such a big difference. Boosted our overall sales, improved our ROAS, and also expanded our new-to-brand buyers," Chris says. "Sometimes it wasn't like the biggest risk necessarily, but it was one of those moments where we just completely changed everything we were doing because we realized how we had set up the campaign wasn't in our best interest."
"One of the great things I think about retail media is that you can pivot quickly. You can make really bold moves when the data calls for it."
The Bottom Line
These stories reveal that the biggest risk often isn't taking the leap—it's standing still. Whether it's trading traditional media for earned impressions, betting on unproven products, going dark during peak hours, or abandoning your best-performing keyword, these leaders show that calculated risks based on strategic thinking can deliver outsized returns.
The key isn't being reckless—it's being willing to challenge conventional wisdom when the opportunity presents itself. As these leaders demonstrate, sometimes the safest path forward requires taking the biggest leap.
