Principal, CEO Office

Company Description We’re Checkout.com . You might not know our name, but companies like eBay, Spotify, Klarna, Uber, and Sony do, because we’re behind many of the digital experiences you use every day. We are where the world checks out, enabling over 10 billion transactions yearly for more than one billion global shoppers. Whether you want to book a holiday, order food, renew a subscription, or check out online, there’s a good chance our tech powers the payments behind the scenes. Our platform helps the most ambitious businesses deliver effortless digital experiences, at scale. If you want to do career-defining work, you’ve come to the right place. We move fast, think globally, and believe great teams are built by hiring exceptional people with conviction, curiosity, and the desire to make an impact. With 20 offices across six continents and London as our HQ, we’re shaping the future of fintech – and we’re just getting started. Job Description We are looking for a high-judgment, high-ownership operator to join the CEO Office and turn the company's most important priorities into outcomes: someone driven, hungry and talented, comfortable balancing strategic thinking, research and decision-making with hands-on delivery and operational rigour. We collaborate with a wide range of teams across the organisation to drive maximum impact. The CEO Office has a broad remit spanning strategic planning, cross-functional execution, leadership support, and special projects. You will bring structure to ambiguous problems, drive complex work across teams, and combine analytical rigour with hands-on delivery. This is an opportunity to become a trusted partner to leadership and a force multiplier across Checkout. How You'll Make an Impact You will support Checkout’s CEO and Head of CEOO to drive critical cross-functional initiatives by assuming day-to-day project leadership and enabling cross-departmental collaboration You will help Checkout’s departments scale by establishing clear organisation structures, setting objectives and KPIs and implementing robust processes You will identify the most complex and critical problems, design the solution, build the process or system that makes it durable, and drive to a measurable business outcome You will help leadership navigate ambiguity, accelerate execution and drive cross-functional alignment across the company You will operate across strategy and execution: taking ownership of ambiguous, high-priority problems, especially those spanning multiple teams or lacking a natural owner You will navigate open-ended problems, including identifying and defining the problem before developing and implementing effective solutions Projects may include: organisational model design, international expansion strategy, scaling new business lines globally, goal setting and strategic planning, go-to-market execution, regulatory, data and financial infrastructure initiatives, board & shareholder reporting What We're Looking For Strong problem-solving and analytical skills: You break problems down into components, move comfortably between strategic thinking and operational detail, and build your own analyses and models rather than commissioning them Excellent communication skills: clear and concise, with experience working with senior executives. You build relationships across teams, resolve conflicts, and drive alignment across functions with competing priorities, without formal authority Comfort with unknowns: You enjoy steep learning curves and believe in first-principles thinking. You analyse problems and use data to inform decisions, optimise processes and track performance. You are comfortable with shifting priorities, ambiguity, and fast-moving environments Humility and low ego: You are an ambassador for our mission, values and operating principles AI-native way of working: You reach for AI tools first to research, analyse, build and automate, and you make yourself measurably faster with them Builder mindset: You'…