Principal, CEO Office

We’re the company behind many of the digital experiences you use every day, enabling over 10 billion transactions yearly for more than one billion global shoppers. Our platform helps ambitious businesses deliver effortless digital experiences at scale. 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.

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. You will 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.

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.

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.
• 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’d rather own the outcome than the recommendation, and you have evidence of building things that lasted beyond your involvement.
• A track record of impact: quantifiable business outcomes, rapid growth in responsibility, and competitive achievements inside or outside work.
• Experience in consulting, high-growth technology companies, investing, investment banking, strategic finance, or similarly high-performance environments.

Bonus Points

• Exposure to payments, fintech, or money movement.
• You have built low-code/no-code or AI automations that others still use.
• Advanced SQL or hands-on data analysis skills.
• International experience across multiple markets and cultures.
• Entrepreneurial experience: founded or helped build something from scratch.

The CEO Office helps Checkout focus on what matters most and turn problem statements into business outcomes. As you build context, trust, and execution credibility, you can expand your scope into broader strategic and operational topics owned or incubated by the CEO Office.

Additional Information

We create the conditions for high performers to thrive, through real ownership, fewer blockers, and work that makes a difference from day one. Here, you’ll move fast, take on meaningful challenges, and be recognised for the impact you deliver. It’s a place where ambition gets met with opportunity, and where your growth is in your hands. We work as one team, and we back each other to succeed.

Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.