checkout.com - Chief of Staff

• 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.