Role overview

Checkout.com is seeking a Chief of Staff to work directly with the Chief Revenue Officer, supporting the global commercial organization that spans Sales, Account Management, Partnerships, Solutions Engineering, Revenue Operations, and Pricing across all regions. This is a strategic, hands-on role—not an administrative position—where you will act as the CRO’s trusted advisor and operational right hand, enabling faster decision-making and alignment across the commercial leadership team.

Key responsibilities

Serve as a thought partner to the CRO, pressure-testing ideas, offering independent perspective, and translating strategy into clear, accountable actions.
Represent the CRO in internal forums and make delegated decisions on their behalf when required, including during their absence.
Collaborate with revenue leaders on deal strategy for major merchants and coordinate executive engagement to accelerate new and existing opportunities.
Monitor the global pipeline and forecast closely, hold revenue leaders accountable for their commitments, and identify risks and opportunities early.
Own the CRO’s leadership cadence by designing and running leadership meetings, business reviews, and decision forums with clear purposes and accountable outcomes.
Exercise delegated approval authority on pricing, offers, and hiring requisitions, applying agreed frameworks consistently and escalating when needed.
Lead annual and quarterly planning work with Revenue Operations and Finance, covering targets, headcount planning, budgets, and OKRs.
Drive the Commercial organization’s hiring plan governance, ensuring capacity planning aligns with revenue priorities and budget constraints as the company scales.
Design and execute Commercial Leadership Summits and offsites, including agenda development, content curation, and accountability follow-up.
Serve as the main liaison between the Commercial organization and Operations, Product, Finance, Legal, Compliance, Marketing, and People leadership.
Surface cross-functional blockers affecting revenue, frame them clearly, convene the right stakeholders, and push for resolution.
Partner with Operations, Legal, and Compliance on initiatives to reduce time to revenue for new merchants.
Own strategic initiatives from inception to completion, typically with defined revenue or efficiency targets and involvement from multiple teams.
Identify opportunities to simplify processes, governance, and tools—including through AI and automation—to increase Commercial team productivity.
Prepare the CRO for key meetings and presentations, including executive, board, all-hands, customer, and external speaking engagements, with pre-reads, briefings, speaker notes, and follow-ups.

Requirements

At least 5 years of experience in roles such as Chief of Staff, strategy consulting, commercial or revenue strategy, or business management.
Ideally, relevant experience in high-growth technology, fintech, or payments companies.
Strong commercial instinct with demonstrated understanding of revenue generation through pipeline management, pricing, unit economics, and forecasting, and comfort diving into deal details.
Sound judgment to exercise delegated authority on approvals, balancing commercial speed with appropriate discipline and knowing when to escalate.
Proven ability to influence senior leaders without formal authority, including resolving disagreements and reaching clear outcomes.
Excellent structured thinking and communication skills, capable of distilling complex, ambiguous problems into clear recommendations and writing executive-ready materials.
Strong analytical skills with confidence in working with data and financial models to support decision-making.
Demonstrated project and programme management expertise with the ability to switch between contexts while maintaining focus.
Ability to handle confidential people, commercial, and financial information with appropriate discretion.
Low-ego, high-ownership mindset—comfortable both executing work independently and orchestrating others to complete it.

What makes this role worth considering

This position offers the opportunity to work at a significant scale within a company that processes over 10 billion transactions annually for more than one billion global shoppers, powering payments for major brands like eBay, Spotify, Klarna, Uber, and Sony. Based in London with 20 offices across six continents, Checkout.com is a rapidly growing fintech company where you will have real ownership, fewer blockers, and the chance to make a meaningful impact from day one.