Scratch: CMO Interviews

Checkout.com’s Playbook for Beating Global Giants: Pick One Fight.

Episode Summary

Checkout.com processes billions in digital payments for brands like Spotify, eBay, Uber, and Pinterest. But when your card works 99.9% of the time in-store and only 80% online, that gap costs millions.

Episode Notes

Rory O'Neill, CMO of Checkout.com, doesn't just solve for payments- he's solving for brand preference in a crowded payments space. And he's doing it by competing on what's different, not what others do better.

That insight changes everything, from how you position payments to how you build a team that can sustain growth as a challenger.

In the latest episode of Scratch, Rory breaks down the playbook that lets Checkout compete with global giants. Brand preference wins 95% of B2B deals before salespeople ever show up- so your marketing owns the invisible 60% of the buyer's journey. Challenger brands win by picking one fight and building culture around it, not chasing everything competitors do. He reveals the three-part formula: focus your core business, build your culture, reinvest profit. Consumer marketing skills-data, insight, action-are B2B's secret superpower. And his rule: if you wouldn't say it at dinner, don't write it in marketing.

The key takeaway:

  1. Brand preference wins deals - 95% of the time, the brands on the day-one top-five list are the ones that win. B2B buyers spend 60% of their journey before contacting a salesperson.
  2. Define your focus as a challenger - Compete on what's different, not on what competitors do better. Checkout only does digital payments to stay focused while competitors spread across multiple business lines.
  3. Three elements beat category norms - Focus on your core business, build the human operating system (culture, people, vision), then reinvest capital in new products.
  4. Consumer marketer skills are powerful in B2B - Data, insight, action, brand building, and performance marketing from the consumer world unlock B2B success.
  5. Understand stakeholder maps - B2B is complex: CTOs influence CFOs, recommenders influence buyers. Map those relationships to win.
  6. Simplify your language - Ditch jargon like "frictionless" and "seamless." Use words you'd use at dinner. Marketing becomes more interesting and understood.
  7. Marketing is logic and magic - Be both data-driven and creative. Avoid letting fiefdoms kill integrated work. Join everything together.

Watch the video version of this podcast on Youtube ▶️: https://youtu.be/chR0mn9Pum0

Scratch is a production of Rival, a marketing innovation consultancy that develops strategies and capabilities that help businesses grow faster. Scratch is hosted by Eric Fulwiler, and he's joined by Rory O'Neill of Checkout.com in this episode.

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