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.

The CEO Office

The CEO Office works with senior leaders across Checkout.com on high-priority strategic and operational problems. The team turns important questions into clear decisions, coordinated execution and measurable business outcomes.

The role

This is a manager-level individual-contributor role for a hands-on operator. You will own defined, high-priority, cross-functional initiatives end to end—from framing problems and aligning stakeholders to implementing solutions and delivering measurable outcomes.

Working closely with the Head of the CEO Office, you will combine structured problem-solving with hands-on execution. You will translate priorities into coordinated action, strengthen how teams operate and drive initiatives through to impact.

This is neither a traditional PMO nor a presentation-led strategy role, and it is not an executive-level position. Success requires sound judgement, analytical rigour, clear communication, operational follow-through and the ability to influence effectively without formal authority.

How You'll Make an Impact (Role overview)

• Support the CEO and Head of the CEO Office on critical cross-functional initiatives by helping coordinate day-to-day delivery, stakeholder collaboration and progress towards measurable outcomes.
• Help investigate complex, ambiguous problems by clarifying the problem, developing practical solutions and supporting the implementation of durable processes or systems.
• Support departments in scaling by contributing to organisation design, objectives and KPI setting, and the development of robust operating processes.
• Assist leadership in navigating ambiguity by surfacing insights, decisions and risks, coordinating follow-through and supporting alignment across teams, particularly where there is no natural owner.
• Projects may include organisational model design, international expansion strategy, scaling new business lines, strategic planning and goal setting, go-to-market execution, regulatory, data and financial infrastructure initiatives, and supporting board and shareholder reporting.

What We're Looking For (Background and core competencies)

• Relevant background and impact: Experience in a fast-paced, high-performance environment.Relevant backgrounds include consulting, high-growth technology, investing, investment banking, strategic finance or entrepreneurial operations. Payments or fintech exposure and international experience are advantages.
• Problem-solving and analytical rigour: Use first-principles thinking, data and judgement to structure ambiguous problems, identify key measures and move between strategic questions and operational detail. Advanced SQL or hands-on data analysis is a plus.
• Building and execution: Turn analysis into practical plans, KPIs, processes, tools or systems that create durable value. Experience building low-code/no-code or AI automations that others continue to use is a plus.
• Ownership and impact: Personally own cross-functional work and deliver measurable outcomes.
• Influence and collaboration: Build trust, navigate trade-offs and make progress across functions without formal authority, with a low-ego and collaborative approach.
• Learning agility and entrepreneurial mindset: Learn quickly, respond well to feedback, adapt to changing priorities and show evidence of creating, launching or materially improving something from scratch. Founding or entrepreneurial experience is valued but not required.

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