Checkout.com’s CMO on simplifying complexity and winning the brand game

As fintech platforms evolve, adding layers of functionality from lending to business accounts, the challenge for marketing leaders is immense. How do you communicate an increasingly complex value proposition without overwhelming the enterprise clients you aim to serve? For Checkout.com, the answer is radical simplicity.

Rory O’Neill, Chief Marketing Officer at Checkout.com tells us about the art of simplifying the message, the strategy behind building a trusted enterprise brand, and the future impact of agentic commerce on the digital economy.

The Paradox: More Products, Simpler Story

Checkout.com has expanded far beyond its payment processing roots, now offering everything from fraud protection and AI-driven acceptance tools to BNPL integrations and business accounts. Yet, as the product suite grows, O’Neill insists the marketing must become simpler.

“As we build more and more products in the network, and arguably it becomes more and more complex, our marketing has to change so that it becomes more simple,” O’Neill stated. “You can’t communicate all those things all at once.”

The company’s north star is a singular focus on its core audience and their primary need. “We’re focused on enterprise businesses, those that really shape the digital economy, and what they care about more than anything is payment performance,” he explained. Every product, from AI to acquiring, is framed as a tool to achieve that one goal. This disciplined approach prevents what he calls the “Microsoft version of the iPod”—a beautifully simple concept made complicated by trying to communicate every feature at once.

Building a Brand on Trust and Endorsement

In the high-stakes world of enterprise payments, brand building is less about flashy campaigns and more about cultivating trust. O’Neill revealed that their research shows a staggering “70% of all payment buyers have a preferred payment service provider before they start their journey.” This insight shapes Checkout.com’s entire strategy, moving beyond traditional marketing to foster deep relationships and powerful endorsements.

High-profile partnerships with giants like eBay are a cornerstone of this approach. Rather than focusing on themselves, the marketing celebrates the merchant. “People in the payments industry know that eBay have an incredible expertise around payments,” O’Neill said. “For us, if eBay endorses Checkout by working with Checkout, that’s the biggest marketing we can have.”

This is complemented by a deep investment in word-of-mouth and peer-to-peer trust. “The payments people trust other payments people,” he noted. This means facilitating connections between their product teams and clients, focusing on Net Promoter Score (NPS), and ensuring every one of their 2,000 employees undergoes extensive payments training to speak with authority and build credibility.

From Global Acquiring to Embedded Finance

Checkout.com’s recent expansion of its direct acquiring capabilities in Japan, Canada, and Brazil highlights its “global message, delivered locally” approach. While the top-line proposition of performance is universal, local marketing teams are empowered to tailor the execution, celebrating local merchants and understanding market nuances. It’s a philosophy born from their CEO’s belief that “all payments are ultimately local.”

The company is also making a strategic move into embedded finance with the “Checkout Business Account.” This offering moves core treasury functions directly into the payments network. “It’s basically moving the core Treasury banking facilities into the payments network so people don’t have to move money out… before they start to let it grow or put it to work,” O’Neill explained. He predicts a shift in language from “free cash flow” to “free payments flow,” signaling a fundamental change in how merchants manage their capital.

The Next Challenge: Marketing to AI Agents

Looking ahead, O’Neill identified the one topic he felt was under-discussed at the conference: the impact of agentic commerce. He believes this will force marketers to fundamentally rethink their primary touchpoint—the website.

“People aren’t going to find you through search anymore, they’re going to find you through their agents,” he predicted. “Brand is going to become super important because agents are going to get ask you for your preferences.”

In this new reality, an AI agent won’t be swayed by website design or emotional copy. It will revert to the core components of commerce: price, brand, availability, shipping, returns policy, and payment method. O’Neill predicts agents will first take over mundane, everyday shopping experiences.

For brands, the challenge will be to build a reputation so strong that they become a user’s stated preference, ensuring the agent finds them first.