PayPal Knows You Bought That Burrito—and Who You Split It With

The Transaction Graph, Venmo Emojis, and How Grether Is Building the Internet’s Next Great Surveillance Ad Network (Without the Creepy PR Team)

Pesach Lattin (ADOTAT)
June 17, 2025

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Published independently. No NDAs. No fluff. Just commerce espionage.

We Spied on PayPal’s Ad Machine — Here’s What They Didn’t Want You to See

For most people, PayPal is the dusty old middleman of the internet—just a legacy brand wedged somewhere between your bank and your Venmo pizza split. A fossil from the dot-com days. A digital checkbook. A punchline.

But walk past the fintech façade, peek into the fluorescent-lit labs of San José, and you’ll find something entirely different brewing—a full-blown adtech Frankenstein stitched together by one of the most methodical minds in the business: Dr. Mark Grether.

We spent weeks embedded with the PayPal Ads team. We met with engineers, strategy leads, and Grether himself—who, frankly, gives off the precise energy of a man who once co-founded Xaxis, ran Amazon’s ad strategy, and built Uber Ads into a billion-dollar business. He didn't cackle in German, but he might as well have.

They gave us “the tour.” What they didn’t realize is that we were watching everything. And while they polished their pitch decks for Cannes, we took notes on the reality: PayPal isn’t just building an ad platform.

They’re building a media operating system for money itself.

Step One: Rename Your Data, Pretend It’s Never Been Seen

The centerpiece of this entire experiment? Something they lovingly call the Transaction Graph. Sounds harmless. Clinical. But make no mistake—this is the most commercially potent surveillance map you’ve never consented to.

We saw it in action. It's not just what you bought. It's when, where, with whom, how often, and in what order. And it’s not a guess. It’s not modeled. It’s the real thing: receipts.

Let’s say you used PayPal to buy Nikes on StockX, a plant-based burger at a ghost kitchen via Venmo, and then browsed Sephora with a Honey coupon you forgot you even installed. That triangle of behavior? Mapped. Merged. Monetized.

This isn't a retail media network locked inside a grocery store’s app. This is a real-time, cross-merchant, cross-platform picture of how money moves—across 400 million users and 30 million merchants, across digital and physical, across your lifestyle.

And unlike cookies, this data doesn’t expire. It doesn’t disappear when Apple gives you a warning. It’s tied to actual verified transactions. Try opting out of your own credit card history.

Step Two: Don’t Build a Feed. Build the Whole Street

Here’s where Grether’s real genius kicks in. Most companies would kill to launch a new media product. A shiny portal. An attention-grabbing experience.

Grether? He doesn't care about eyeballs. He cares about intent. What Uber gave him—context, frequency, immediacy—PayPal gives him in spades. But horizontally. Across the entire ecosystem.

When asked what he saw in PayPal that others didn’t, he laid it out plainly: “We see 25% of global e-commerce. This isn’t just a platform. It’s a two-sided ecosystem—signal and scale. And that means we can do something no one else can.”

That something is bigger than slapping ads on a checkout page. It’s about becoming the connective tissue between consumers and commerce, not on one site—but across all of them.

Retail media today is a junk drawer of siloed platforms. Kroger does Kroger. Walmart does Walmart. You want to know what happens between them? Good luck with your Frankenstein spreadsheet. But PayPal sees everything between the silos. And that’s exactly the moat.

Step Three: Build the Shadow Feed (Hint: It’s Venmo)

Here’s the part that honestly shocked us: Venmo is PayPal’s secret weapon.

Most people think of it as a money app with emojis. In reality, it’s a social commerce graph hiding in plain sight.

We dug into the behavioral signals and… it’s gold. People tag transactions with pizza slices, lipstick, gym flexes, and Sephora trips like it’s a diary. And these aren’t vague “likes” or engagement guesses—they’re timestamped purchase intent tied to real money movement.

According to PayPal’s team, 48% of Venmo users are Gen Z or Millennials. Half of them check the app multiple times a week. And many of them do what Grether calls “shadow shopping”—splitting purchases, coordinating group buys, comparing notes publicly.

It’s TikTok for money—but nobody’s noticed.

And yes, if you’re Domino’s, you can now run emoji-based targeting. Not a joke. 🍕 is an actual audience segment.

Step Four: Go Offsite, Quietly Dominate Everyone Else’s Inventory

The real magic trick? PayPal isn’t just buying its own hype. They’re selling access to their data across the open web.

They’ve launched offsite ads—curated PMPs that let advertisers buy PayPal-powered audiences in other ecosystems. Grether made it clear: they’re DSP-agnostic. They don’t care what pipe you use. As long as you buy into the transaction graph, they’ll let you tap the signal.

Want to target people who bought skis in the last 60 days? People who share pizza every Friday? Parents who split beauty products on Saturdays and order Chipotle on Sundays? That’s not targeting. That’s predictive shopping logic, and PayPal is quietly handing it out to the buyers who know what to ask for.

What Facebook used to do with browsing history, PayPal is doing with actual wallets. The difference? One made you paranoid. The other makes you a better marketer.

So Can They Pull It Off?

Grether thinks so. He’s already done it once at Uber. At Amazon, he helped engineer a machine built on first-party dominance. But this? This is bigger. Because the pitch isn’t just adtech.

The pitch is "we know what consumers do when they spend real money.” Not what they search. Not what they scroll. What they swipe.

There are risks, of course. Consumers are touchy about privacy. The term "data" is radioactive. But PayPal’s secret weapon is trust. They’re not Meta. They’re not scraping browser tabs or harvesting messages.

They’re just doing what you asked: keeping a record of what you paid for—and making that record useful.

Whether that translates into a revenue engine big enough to rival the walled gardens? We’ll see. But from what we’ve seen behind the curtain, they’re not just building a media business. They’re building a new layer of the economy.

Commerce Media with Teeth — Why Marketers Are Betting on PayPal
Or: How PayPal Became the Most Dangerous Ad Network You’ve Never Touched

Retail media used to mean “run some sponsored SKUs on Amazon, pat yourself on the back, and pretend you're innovative.” But now? It means PayPal knows what your customers are buying — across 30 million merchants. They know who just bought pizza, who’s splitting Sephora hauls with three friends, and yes, who panic-bought $300 sunglasses for Cannes.

This isn’t a walled garden. It’s a garden with tentacles.

We spent more time in PayPal’s inner sanctum this month, and the vibe wasn’t "agency case study" or “friendly product walkthrough.” No, this felt like we were peeking behind the curtain at a commerce intelligence lab, run by a few too many people who probably say "machine learning" when they mean “mind reading.”

One of our researchers whispered, “They’re not building an ad platform. They’re weaponizing your wallet.” We laughed. Then we saw the dashboards. We stopped laughing.

Here’s what we found.

🔬 PayPal’s Twin Blades: On-Platform and Off-Platform Ads

PayPal’s ad product isn’t just a bolt-on banner unit in some dusty PayPal.com footer. It’s a two-headed adtech mutant, designed for precision.

Head One: On-Platform Ads.
You’ve seen these if you’ve used PayPal, Honey, or Venmo recently — maybe without realizing it. These aren't generic promos. These are offers crafted from your own financial behavior. Buy Chipotle every Thursday? You’re getting a burrito offer before you even open the app. Split that purchase with two friends who also split beauty products every other week? You’re suddenly on Sephora’s radar.

Grether’s team refers to it as "signal-led curation," which sounds fancy until you realize it just means they’re targeting you based on what you already bought — down to the hour.

Head Two: Off-Platform Ads.
Here’s the fun part. PayPal has now quietly become a DSP-agnostic monster, selling curated PMPs to anyone with a wallet and a briefcase. And it’s not based on clicks or lookalikes — it’s based on transaction-verified purchase behavior. That means if you bought something using PayPal or Venmo, chances are you just became a targetable segment, off-platform, across the open web, streaming apps, mobile… even CTV.

To quote one PayPal engineer, “We don’t follow you. We follow your spending.”

Chilling. Accurate.

🍕🍕 Venmo Emojis: The Most Ridiculous (and Brilliant) Signal in Adtech

Let’s talk about the emojis. Yes, they're real targeting signals. Yes, it’s just as weird as it sounds.

Inside Venmo, there’s a behavioral signal most platforms can only dream of: real-time, peer-validated purchases wrapped in little emoji-coded memos. PayPal’s team is turning these into behavioral clusters — what one strategist called “emoji commerce archetypes.”

If your Venmo feed is full of 🍕, 💄, 🛍️ or 🎟️, congrats — you’re part of a segment. And advertisers can reach you accordingly.

Beauty brands are targeting 💅.
Concert advertisers? 🎶 and 🎤.
Group dining brands are snapping up 🍝 and 🍣.

We saw the dashboards. There are drop-down menus for these. It’s not hypothetical. It’s productized. It’s working.

🧩 Why They’re Calling It “Commerce Media” (Not Retail Media)

This isn’t just semantics. Retail media is siloed. It’s Target selling Target data. Kroger selling Kroger data. But PayPal doesn’t care which store you shopped at — they see the transaction across the entire economy.

They’re watching how you shift from Amazon to Etsy to Shopify. From niche beauty brands to big box stores. From the last thing you bought to the next thing you will.

Marketers are no longer stuck optimizing inside a single store’s sandbox. With PayPal, they’re watching the full graph of your purchase intent — and your competitor’s.

That means:

Market share tracking, in real time
Share-of-wallet measurement
Incrementality analysis across thousands of merchants

If Amazon sells you on conversions, PayPal’s pitching the entire chessboard. And yes, they’re already working with enterprise CFOs to turn this into planning-grade intelligence.

🤖 Inside the AI Lab: Customization at Scale and Democratization for the Little Guys

Here’s where the scientists get a little too giddy.

PayPal’s AI team is working on what they call agentic commerce. AI agents that don’t just optimize bids — they predict intent, generate dynamic creative, and customize offers on the fly.

To the user, it feels like the system knows what you want before you’ve even searched.

To the marketer? It means:

Creative isn’t static — it's modular and personalized.
Offers aren’t batch-blasted — they’re tuned to transaction history.
Micro-merchants get access to tooling once reserved for Dentsu-sized accounts.

They’re already testing AI-powered creative generation for SMBs. Got a boutique jewelry shop using Venmo as POS? They can now run display ads auto-generated from product shots, optimized by PayPal’s AI, served to users who have spent in the same category in the last 72 hours.

And that’s just phase one.

The team kept hinting at something bigger. A future where the ad itself is the storefront — a buy-now layer embedded directly into the ad unit, across publishers, with zero redirects.

They’re not building banner ads. They’re building micro-checkout universes powered by your behavior.

Let’s be clear: PayPal Ads isn’t just trying to “drive conversions.” That’s kindergarten stuff.

They’re aiming for strategic planning firepower — the kind that reshapes how CMOs think about spend, and how CFOs approve it.

Because when you can show who’s buying what, where your brand is gaining or losing momentum, and how your ad budget actually shifts market share across retailers... suddenly you're not an “ad vendor.”

You’re an economic indicator.

TL;DR — You’re Not in a Walled Garden. You’re in a Monetized Maze

PayPal isn’t just another player in the adtech revival. They’re the ones quietly building the operating system for commerce advertising — with trust as the UI and receipts as the logic.

They’re already everywhere your customer spends. Now they want to be everywhere your budget goes.

The question isn’t whether PayPal will become a top-tier ad platform. The question is whether you’ll notice before your competitors do.

🔐 Next Up in Part III:
We dig into the AI firepower behind PayPal's creative engine, explore their SMB blitz, and unpack the full vision for cross-merchant measurement that’s already shaking up agency media plans.

👉 Subscribe to ADOTAT+ to get access — and know more than you did yesterday.

What You’re Missing in ADOTAT+

We pulled back the curtain on PayPal’s plan to turn 225 billion transactions into the most precise advertising engine on the internet—far beyond anything a traditional retail media network can offer. Inside ADOTAT+, you’ll find the full story: how Hugo Boss and Verizon are using PayPal’s transaction graph to measure market share in real time, not just conversions; how cross-merchant attribution is finally solving the “where did my customer go” problem; and why CFOs are now watching media plans like P&Ls.

You’ll also see why Venmo is quietly becoming the most underpriced attention market in commerce. We mapped how PayPal Ads is using pizza emojis, beauty splits, and payment memos to target moments, not demographics—and why it might raise more legal eyebrows than Meta ever did. If you want to understand the ad platform that’s built on trust, not clicks—this is where it starts. Unlock it in ADOTAT+.

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PayPal Knows You Bought That Burrito—and Who You Split It With

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