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'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. The role also offers exposure across Checkout and a pathway into different functions within the company.

Additional Information

Bring all of you to work

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 recognized 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. So whatever your background or identity, if you’re ready to grow and make a difference, you’ll be right at home here.

It’s important we set you up for success and make our process as accessible as possible. So let us know in your application, or tell your recruiter directly, if you need anything to make your experience or working environment more comfortable.

Life at Checkout.com

We understand that work is just one part of your life. Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.

Curious about what it’s like to be part of our team? Visit our Careers Page to learn more about our culture, open roles, and what drives us.

For a closer look at daily life at Checkout.com, follow us on LinkedIn and Instagram