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.
Role overview
We are looking for a talented and commercially minded Chief of Staff to report directly to the CRO. The CRO owns Checkout.com’s global revenue organisation (Sales, Account Management, Partnerships, Solutions Engineering, Revenue Operations and Pricing) across all regions. As the CRO’s right hand, you will extend their reach, speed up decision-making, and make sure the Commercial leadership team is aligned and delivering against its revenue targets.
This is not a back-office role. You will act as the CRO’s delegate on key approvals, work on live deals and pricing decisions, resolve the cross-functional blockers that slow down revenue, and contribute to the planning and operating rhythm of a global commercial organisation. You’ll be a trusted advisor and sounding board to the CRO and their leadership team. You’ll be expected to challenge them, not just support them, and to move comfortably from a board-level narrative to a merchant pricing decision on the same day.
Remit and Responsibilities
- As a thought partner and sounding board to the CRO, pressure-test ideas, bring an independent point of view, and turn strategy into clear, owned actions.
- Represent the CRO in internal forums and make decisions on their behalf when needed, including during absences.
- Work with revenue leaders on deal strategy for our largest new and existing merchants, and set up executive engagement to open or speed up opportunities.
- Stay close to the global pipeline and forecast, hold revenue leaders accountable for their numbers, inputs and follow-ups, and flag risks and opportunities early.
- Own the CRO’s leadership cadence (leadership team meetings, business reviews and decision forums), making sure each one has a clear purpose, clear decisions and accountable owners.
- Act as the CRO’s delegate for key approvals across the Commercial organisation, including pricing, offers and job requisitions. Apply agreed frameworks consistently, challenge where needed, and know when to escalate.
- Partner with Revenue Operations and Finance on annual and quarterly planning, including targets, headcount and capacity planning, budgets and OKRs.
- Drive the governance and prioritisation of the Commercial-wide hiring plan, partnering with Revenue Operations on capacity planning and with Talent Acquisition, People and Finance to keep hiring aligned with revenue priorities and budget as we scale.
- Design and run the Commercial Leadership Summit and other leadership offsites, from agenda and content through to follow-up and accountability.
- Be part of the Commercial organisation’s main link to Operations, Product, Finance, Legal, Compliance, Marketing and People leadership.
- Pick up the issues the Commercial team faces day to day, frame them clearly, get the right people in the room and push for a decision, especially where senior leaders are not yet aligned.
- Work with Operations, Legal and Compliance on initiatives to reduce time to revenue for new merchants.
- Own high-priority strategic initiatives from start to finish, usually with a clear revenue or efficiency target and several teams involved.
- Keep challenging how the Commercial organisation works, and simplify processes, governance and tools to increase productivity, including through AI and automation.
- Prepare the CRO for all key meetings and presentations, including exec and board meetings, All-hands meetings, business reviews, customer meetings and external speaking engagements. This covers pre-reads, briefings, presentations, speaker notes and follow-ups.
Desired Background, Core Competencies
- You have 5+ years of experience in roles such as Chief of Staff, strategy consulting, commercial or revenue strategy, or business management, ideally including time in a high-growth tech, fintech or payments company.
- Strong commercial instinct: you understand how revenue is built through pipeline, pricing, unit economics and forecasting, and you’re comfortable getting into the details of a deal.
- Sound judgement to exercise delegated authority on approvals, balancing commercial speed with discipline and knowing when to escalate.
- A proven track record of influencing senior leaders without formal authority, including handling disagreement between them and getting to a clear outcome.
- Excellent structured thinking and communication: you can reduce complex, ambiguous problems to a clear recommendation and write in a way that’s ready for executives.
- Critical thinker who is confident with data and financial models and uses them to support decisions.
- Excellent project and programme management skills, with the ability to switch contexts without losing focus.
- Discretion when handling confidential people, commercial and financial information.
- A low-ego, high-ownership mindset: you’re as comfortable doing the work yourself as you are orchestrating others.
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
