checkout.com - Strategy and Operations Lead, CEO Office
Requirements
• 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. • Strongly preferred: • 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. • What this role is not: • 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. • 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 http://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 https://www.checkout.com/careers to learn more about our culture, open roles, and what drives us. • For a closer look at daily life at Checkout.com http://Checkout.com, follow us on LinkedIn https://www.linkedin.com/company/checkout/life/ and Instagram https://www.instagram.com/checkout_com/
Responsibilities
• 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. • 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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