Chief of Staff - Commercial

About the role

Checkout.com is looking for a commercially minded Chief of Staff to report directly to the CRO, who owns the global revenue organisation (Sales, Account Management, Partnerships, Solutions Engineering, Revenue Operations and Pricing) across all regions. The role is not back-office: it acts as the CRO's right hand, extending their reach, speeding up decision-making and keeping the commercial leadership team aligned on revenue targets. It sits in London.

Key responsibilities

• Act as a thought partner and sounding board to the CRO, pressure-test ideas and turn strategy into owned actions.
• Represent the CRO in internal forums and make decisions on their behalf, including during absences.
• Work with revenue leaders on deal strategy for large new and existing merchants and set up executive engagement.
• Stay close to the global pipeline and forecast, hold revenue leaders accountable and flag risks and opportunities early.
• Own the CRO's leadership cadence: meetings, business reviews and decision forums, with clear purpose, decisions and owners.
• Delegate key approvals (pricing, offers, job requisitions) and escalate when needed.
• Partner with Revenue Operations and Finance on annual and quarterly planning, targets, headcount, budgets and OKRs.
• Drive the governance of the commercial hiring plan and run the Commercial Leadership Summit and other offsites.
• Be the main link between Commercial and Operations, Product, Finance, Legal, Compliance, Marketing and People, and drive initiatives to reduce time to revenue for new merchants.
• Own high-priority strategic initiatives and simplify processes, governance and tools, including through AI and automation.
• Prepare the CRO for key meetings, including board and executive meetings, all-hands, business reviews and external speaking.

Required profile

• 5+ years in roles such as Chief of Staff, strategy consulting, commercial or revenue strategy, or business management, ideally in a high-growth tech, fintech or payments company.
• Strong commercial instinct: understanding of pipeline, pricing, unit economics and forecasting, and comfort with deal details.
• Sound judgement on delegated authority, and a track record of influencing senior leaders without formal authority.
• Excellent structured thinking, communication and project management; discretion with confidential information.

What we offer

• Hybrid working: three days per week in the office.
• A culture of ownership, fewer blockers and meaningful work from day one.