For Rory O’Neill, the challenge of fintech marketing isn’t awareness. It’s clarity.

As CMO of Checkout.com, a company that has quietly scaled into one of the most sophisticated digital payments infrastructures globally, O’Neill’s mandate spans pipeline performance, brand longevity, and team culture. But beneath the job description is a strategic tension: how do you simplify a product that’s becoming more powerful and more complex by the day?

Speaking on the ground at Money20/20 Europe, O’Neill shared how his team is navigating everything from embedded accounts and AI-led fraud tools to global brand lift and the looming impact of agentic commerce.

As Checkout.com’s platform grows to include business accounts, BNPL integrations, and performance AI layers, its brand story faces a common risk: feature overload.

O’Neill is clear-eyed about the temptation. Product teams want every feature showcased. But in high-stakes enterprise sales, simplicity is the real differentiator. For Checkout.com, that means distilling a growing product portfolio into a single, defensible focus: payment performance for digital-first enterprises.

Every expansion, be it fraud protection, alternative payment methods, or AI-enhanced routing, is positioned as serving this one goal. It’s a classic fintech dilemma turned on its head: as the product becomes more complex, the marketing must become more intuitive.

When Checkout.com announced its global acquiring deal with eBay or its BNPL partnership with Tabby, the message wasn’t about itself. It was about trust.

O’Neill described a deliberate strategy of letting merchants lead. Rather than center Checkout in the story, his team co-markets in ways that elevate the partner’s credibility and use case. It’s a B2B marketing approach more akin to editorial sponsorship than product placement, subtle, contextual, and trust-enhancing.

The result? Real-world proof that the platform performs under pressure, endorsed by brands that other payments buyers already trust. That word-of-mouth ecosystem, he emphasized, is the most durable marketing asset Checkout has.

As Checkout.com expands acquiring capabilities in markets like Japan, Brazil, and Canada, its marketing function is designed to mirror the structure of its product: globally consistent, locally attuned.

Each regional launch pairs licensed infrastructure with boots-on-the-ground teams ensuring not just regulatory compliance, but cultural fluency. O’Neill’s team works in tandem with local commercial teams, adapting tone, language, and positioning without diluting the core message: enterprise-grade payment performance, globally available.

While the top-line narrative is universal, the execution is anything but.

Few challenges haunt B2B marketing leaders more than the debate over brand investment versus performance ROI. O’Neill doesn’t dodge it.

At Checkout.com, the team proves performance value first tracking how marketing touchpoints influence deal size, velocity, and close rates. But that data becomes the bridge to justify longer-term brand investment. The logic: once marketing earns its place at the commercial table, it can advocate for brand with real credibility.

Checkout runs brand recognition surveys by persona, geography, and vertical. It also uses Net Promoter Score (NPS) as a core signal not just of customer satisfaction, but as a proxy for referral likelihood. It’s a brand system rooted in enterprise buying behavior, not awareness vanity.

Checkout.com’s product roadmap is quietly reshaping how treasury and payments infrastructure converge. With the introduction of its business account product, merchants can now keep money within the network, accelerating collections, earning yield, and triggering multi-party flows without extracting funds into traditional banking environments.

O’Neill positioned this not just as a product, but as a reframing of how payments power growth. It’s not just about cash flow. It’s about “free payments flow”, a tighter, faster circuit for enterprise liquidity.

It’s a move that subtly edges Checkout into embedded finance, but without chasing the narrative. The product solves a real operational pain. The marketing, accordingly, lets the utility speak first.

One of the most forward-looking parts of the conversation came in the final minutes, as O’Neill reflected on the rise of agentic commerce AI agents making buying decisions on behalf of users.

If search dies and agents dominate, what happens to the marketing funnel? What happens to brand emotion when the buyer is software?

For O’Neill, the implication is that websites will lose primacy. Agents will index on availability, delivery windows, payment options, and brand trust less on design or messaging. That makes brand reputation more important than ever. Because if an AI agent is filtering options, only the most relevant, trusted, and performance-proven providers will make it through.

The takeaway? Brand isn’t just for people anymore. It’s for machines, too.

Checkout.com has long operated as the invisible engine behind enterprise commerce. But in an era where trust, infrastructure, and product convergence matter more than ever, its brand is no longer optional.

Rory O’Neill’s team is showing how to market complex systems without complexity. By keeping the merchant at the center, letting performance speak, and preparing for the future of agentic decision-making, they’re doing what few fintechs manage to do: scale credibility at enterprise speed.

Earlier today, Rory also joined Amazon Pay and Flutterwave on the main stage to explore how fintech brands earn genuine traction from storytelling and trust to metrics that actually matter.
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