Strategy and Operations Lead, CEO Office

Company description

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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.

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We are where the world checks out, enabling over 10 billion transactions yearly for more than one billion global shoppers.

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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.

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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.

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With 20 offices across six continents and London as our HQ, we’re shaping the future of fintech – and we’re just getting started.

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About The Team

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We’re building Strategy & Operations in the CEO Office to help Product and Engineering deliver the right work, at pace and with fewer surprises. Product sets what to build and why. Engineering builds it. S&O keeps the full picture in view, brings teams together and helps turn plans into results.

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As S&O Lead, you’ll own that work across a product pillar and help raise the bar for how the wider S&O team operates. The impact is visible: what you improve in your pillar can shape how Checkout delivers elsewhere.

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The role

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This is a high-ownership role. You’ll be accountable alongside the product leader for delivery, but you won’t own the roadmap. You’ll need to earn alignment, challenge commitments and stay close to the work. When priorities collide, you’ll help decide what moves, what waits and what stops.

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You will

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• Keep the pillar’s major initiatives in view. Know what matters, what is slipping and where teams are blocked. Raise risks early and bring a clear point of view.
• Be a trusted, independent partner to the product leader. Challenge dates and trade-offs, and help agree what to protect, move or stop. Product retains roadmap decisions.
• Personally lead the pillar’s hardest cross-functional work, from getting teams aligned through to launch.
• Build and lead the S&O team in your pillar. Hire, develop and manage performance, while setting practical standards that help S&O deliver better across Checkout.

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What you'll do

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• Own execution across the pillar. Keep priorities, delivery tempo, progress, dependencies and risks visible. Spot when plans are off track and bring a clear recommendation.
• Build deep expertise in the pillar’s products: how they work, who they serve and how they make money.
• Challenge priorities and commitments with the product leader. Recommend what to protect, re-sequence, move or stop. The product leader owns roadmap and commit-date decisions.
• Personally lead the pillar’s most important cross-functional initiatives, aligning Product, Engineering and partner teams and driving the work through launch to enable faster shipping.
• Lead and develop the S&O team supporting the pillar. People leadership is core to the role, including hiring, development and performance management. Alongside pillar delivery, help shape practical standards adopted across S&O.

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What you'll bring

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• You have strong problem-solving and analytical skills. You can frame an ambiguous business question, build the analysis yourself, test hypotheses, quantify trade-offs and turn findings into clear business decisions.
• You move between strategy, hands-on delivery and building the organisation. You personally lead high-impact, cross-functional work and stay accountable through launch and results.
• You make execution repeatable. You build practical operating mechanisms and use data, automation or AI where they remove recurring friction or help teams scale.
• You influence without relying on authority. You challenge senior stakeholders constructively, communicate complex issues clearly and bring people to decisions.
• You raise the performance of others. You set clear expectations, give direct feedback and help people grow. Prior formal line-management experience is helpful, but evidence of leadership matters more.

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Strongly Preferred

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• Payments, fintech or regulated money-movement experience would be a real advantage, especially if you’ve worked with licences, regulators, schemes or banking partners. It can help you see risks sooner and get up to speed faster. It isn’t a requirement: strong operators from other sectors can be a great fit.

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What This Role Is Not

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• Not support to the product leader. You own execution across the pillar and need to push back when commitments don’t add up.
• Not a short-term consulting project. You stay with the work through delivery and build ways of working the team can keep using.
• Not a product role. Product sets the roadmap. Engineering builds the product. You make sure the pillar executes well.

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Additional Information

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Bring all of you to work

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We create the conditions for high performers to thrive, through real ownership, fewer blockers, and work that makes a difference from day one.

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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.

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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.

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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.

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Life at Checkout.com

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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.

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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.

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