Chief Of Staff

Company Description

We’re Checkout.com – you might not know our name, but companies like eBay, ASOS, Klarna, Uber Eats, and Sony do. That moment when you check out online? We make it happen.

Checkout.com is where the world checks out. Our global network powers billions of transactions every year, making money move without making a fuss. We spent years perfecting a service most people will never notice. Because when digital payments just work, businesses grow, customers stay, and no one stops to think about why.

With 19 offices spanning six continents, we feel at home everywhere – but London is our HQ. Wherever our people work their magic, they’re fast-moving, performance-obsessed, and driven by being better every day. Ideal. Because a role here isn’t just another job; it’s a career-defining opportunity to build the future of fintech.

Job Description

Role overview

We are looking for a highly capable Chief of Staff to support an executive who holds both the Chief Operating Officer (COO) and Chief Human Resources Officer (CHRO) roles.

This is a high-impact, cross-functional role designed to provide leverage, structure, and analytical rigour across a broad operational and people agenda. The Chief of Staff will work closely with the COO/CHRO to help translate strategy into execution, drive key initiatives forward, and ensure clarity, prioritisation, and follow-through across multiple workstreams.

This role is ideal for someone with a background in Operations, HR, or management consulting, who thrives in ambiguity, is highly data-driven, and is comfortable working with senior stakeholders across the business.

What you’ll do

Strategic & operational support

• Act as a trusted thought partner to the COO/CHRO, helping to structure problems, analyse options, and drive clear recommendations
• Support the translation of strategic priorities into executable plans across Operations and People agendas
• Help manage competing priorities, sequencing work and surfacing trade-offs clearly

Data, insights & decision support

• Build and maintain dashboards, analyses, and insights across operational and people metrics (e.g. workforce data, performance indicators, delivery milestones)
• Use data to identify risks, trends, and opportunities, and to inform executive decision-making
• Prepare clear, concise materials for leadership meetings, reviews, and updates

Project & initiative management

• Own and drive multiple projects simultaneously, often across Operations and HR, from definition through to delivery
• Track progress, dependencies, risks, and outcomes across key initiatives
• Bring structure to ambiguous or fast-moving workstreams, creating clarity where it does not yet exist

Stakeholder & leadership engagement

• Work effectively with senior leaders across the company (beyond your direct executive) to align on goals, inputs, and execution
• Support preparation for leadership meetings, including agenda setting, pre-reads, and follow-ups
• Act as a connective tissue between teams, ensuring information flows smoothly and decisions are clearly communicated

Business rhythm & hygiene

• Help ensure leadership forums and operating rhythms are effective, well-run, and outcome-focused
• Capture decisions, actions, and accountability, and ensure follow-through
• Continuously identify opportunities to improve how the organisation plans, executes, and communicates

What we’re looking for

Experience & background

• 5+ years of professional experience, ideally in:
  • Operations
  • Human Resources / People teams
  • Management consultancy (particularly operations, organisation, or people-focused work)
• Experience working in fast-moving, growth-oriented environments
• Exposure to senior stakeholders and complex, cross-functional work

Skills & Capabilities

• Highly analytical and data-driven: comfortable working with metrics, dashboards, and structured analysis
• Strong project management skills, with the ability to manage multiple priorities at once
• Excellent stakeholder management skills, including confidence working with senior leaders
• Able to operate effectively in ambiguity, bringing clarity, structure, and momentum
• Clear, concise communicator — able to synthesise complex information for executive audiences
• Strong judgement, discretion, and professionalism

Ways of working

• Proactive, organised, and execution-focused
• Comfortable switching context frequently without losing attention to detail
• Curious, pragmatic, and outcomes-oriented
• High integrity and trusted with sensitive 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.