Scratch: CMO Interviews · 2026-06-10 · 40 min
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: 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.
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