FROM TARGET CARTWHEEL TO FIRST PARTY DATA

From Target Cartwheel to First-Party Data: Dave Glaza on The Curiosity Current

DIGITS CEO Dave Glaza joins The Curiosity Current podcast to unpack how retail media evolved from Target Cartwheel into first-party data strategy.

The Retail Media Origin Story, Straight From the Room Where It Happened

DIGITS Founder and CEO Dave Glaza recently joined Molly and Stephanie on AYTM’s The Curiosity Current podcast to talk through how retail media grew from a scrappy coupon experiment into one of marketing’s fastest-growing categories. Dave was there for the inflection point. As a member of Target’s original Cartwheel team, he watched a single shoe promotion sell so fast that a Target VP called to shut it down. That moment, years before anyone called it “retail media,” is where this conversation starts.

Retail media budgets keep growing, but most brand marketers still cannot cleanly define the category. Retailer ecosystems keep multiplying beyond Walmart and Target into regional grocers and alcohol retail, and attribution keeps getting more sophisticated. Dave’s conversation gives brand teams a grounded way to think about all three shifts at once, from someone who built the infrastructure on the retailer side before running an agency on the brand side.

Key Takeaways at a Glance

Retail media is the digital evolution of slotting fees and weekly ad placements, now powered by first-party shopper data.

The real unlock is closed-loop measurement: tying a digital ad to an in-store purchase, even though roughly 75 percent of omnichannel transactions still happen at a physical register.

Retailer fragmentation, managing Walmart, Target, and dozens of regional grocers, is one of brands’ biggest operational headaches.

A good retail media experience serves shoppers relevant products. A poor one buries what shoppers are actually searching for.

Dave’s advice for overwhelmed marketers: publish more content, more often, and stop waiting for perfect.

What Did Building Target Cartwheel Teach Dave About Retail Media?

Cartwheel taught Dave that a strong brand paired with a genuinely useful digital experience can shift purchase behavior faster than anyone expects.

Dave described early skepticism inside Target about whether shoppers would sort through hundreds of digital coupons. That skepticism disappeared once Cartwheel reached 40 million shoppers, some of whom browsed deals from the parking lot before walking into the store. The team also expected a Facebook-powered social sharing feature to drive engagement. It did not. Shoppers cared less about a friend activity feed and more about how that behavioral data quietly improved the coupons they saw. Engagement as spectacle lost to engagement as useful personalization, a distinction that still shapes how DIGITS builds client programs today.

How Should Brands Actually Define Retail Media?

Retail media is the digital evolution of what brands always paid retailers for, shelf space and weekly ad placements, now delivered through paid search, onsite, offsite, and social.

Dave was direct that the definition keeps shifting because channels keep multiplying: paid search, then onsite placements, then offsite audiences, then social. Each new channel adds a line item for brand teams to manage. The through line is first-party data. Retailers who know a shopper’s identity and purchase history can reach that shopper anywhere on the open web and, increasingly, tie the exposure back to a physical purchase.

Brands that treat every new channel as an unrelated discipline will struggle to keep up. Brands that recognize first-party identity as the common thread can evaluate new channels faster.

What Makes Retail Media So Attractive to Brand Budgets?

Retail media closes the attribution gap that has frustrated marketers for decades by directly connecting ad spend to sales, even when the purchase happens in a physical store.

Dave pointed to closed-loop attribution as the real driver of retail media growth. Because retailers can identify a shopper through login, loyalty, or payment data, they can serve targeted media and then confirm whether that shopper converted, often in-store, where roughly 75 percent of omnichannel purchases still happen. Brands that once had to guess whether a campaign worked can now see a defined return, even a disappointing one. Marketers would rather have a measurable bad result than an unmeasurable good one, because a measurable result gives them a path to optimize.

New formats are chasing the same proof. Dave cited in-store audio ads testing minute-by-minute sales lift, and Amazon’s new leakage reporting, which tracks whether an Amazon ad drove a sale at a competing retailer.

What Is the Biggest Operational Challenge Brands Face Today?

Fragmentation. Brands increasingly manage retail media across dozens of retailers, not just Walmart and Target, and most headquarters teams are not built for that scale.

Dave was candid that agencies like DIGITS are part of the fragmentation story, since DIGITS helps regional grocers stand up their own retail media networks. He framed the fix as a shared responsibility: better APIs and integrations so brand teams do not have to manually manage relationships with every regional grocer that moves meaningful volume of their product.

This is the exact problem DIGITS was built to solve. Supporting a network of regional grocers alongside Target and alcohol retail media gives brands one point of coordination instead of a dozen disconnected vendor relationships.

What Separates a Good Retail Media Strategy From One That Feels Promotional?

Relevance. The best experiences serve shoppers content that matches what they are actually searching for, rather than maximizing ad inventory at the expense of intent.

Dave shared a personal example: searching for craft beer on a major retailer’s site and getting three full scrolls of mass-market macro beer before anything craft appeared. He argued that clean first-party data and a marketer with a strong point of view on ad quality are both required to avoid that outcome. Retail media teams that chase inventory without protecting shopper experience win short-term revenue and lose long-term trust.

It is worth asking retail media partners how they balance inventory sales against search relevance, and demanding that your own investment shows up in a way that matches shopper intent.

Action Steps: What Brands Can Do Next

• Audit your retail media definition. Make sure your team sees first-party data as the connective thread across channels, not separate disciplines.
• Ask partners how they measure closed-loop attribution. If they cannot explain how digital exposure connects to in-store purchase, that is a gap.
• Map your retailer fragmentation. List every retail media platform you manage, including regional grocers, and evaluate whether you need a coordinating partner.
• Evaluate ad relevance from the shopper’s seat. Search your own category on retailers where you advertise and check whether results serve intent or just inventory.
• Publish more, perfect less. Consistent, good-enough content posted often will outperform infrequent, over-polished content.

FAQs

What is retail media in simple terms? Advertising purchased directly through a retailer, using that retailer’s first-party shopper data for targeting and measurement. It replaced slotting fees and print ads with digital placements across search, onsite, and offsite channels.

How does closed-loop attribution work in retail media? Retailers identify shoppers through logins, loyalty, or payment data, then track whether that shopper saw an ad and later purchased, including in-store, giving brands a direct measure of campaign impact.

Why do brands struggle with retail media fragmentation? Most teams are built to manage a handful of major retailers. As regional grocers and alcohol retailers build their own networks, brands need more integrations than headquarters teams typically have bandwidth for.

What did Target Cartwheel have to do with retail media? Cartwheel, the digital coupon app Dave helped build at Target, used first-party shopper data to influence purchase behavior in real time. It later evolved into Target Circle and is widely referenced as a precursor to modern retail media.

Retail Media Rewards Brands Who Understand the Full Picture

Dave’s conversation makes one thing clear: retail media works because it closes a measurement gap that has frustrated marketers for decades, but only when brands understand the first-party data driving it and the fragmentation that comes with scaling across retailers. Which part of your strategy needs the most attention right now: measurement, fragmentation, or shopper experience?

The full conversation covers more ground on personalization, Amazon’s leakage reporting, and how DIGITS approaches client innovation. Listen to the complete episode of The Curiosity Current, brought to you by AYTM, on Apple Podcasts, Spotify, YouTube, or wherever you get your podcasts.

About DIGITS Agency

DIGITS is an omnichannel retail media agency specializing in Target, regional grocers, and alcohol retail media. As a Target Managed Services partner, Roundel Media Studio Certified agency, and Walmart Connect Partner, DIGITS helps CPG brands navigate retail media with strategic planning, hands-on campaign management, and proprietary analytics. Learn more at www.digitsagency.com.

Dave Glaza, Founder & CEO of DIGITS, remains committed to bringing digital capabilities to physical stores.

LinkedIn: https://www.linkedin.com/in/davidglaza/

Follow DIGITS on LinkedIn: https://www.linkedin.com/company/digits-agency/