UK | Hybrid | Full-time
Reports to: CEO

flatfair is entering an ambitious phase of growth.

We are scaling multiple products, evolving how we go to market and taking on an increasing number of strategic priorities across the business. As that complexity grows, so does the challenge of turning good decisions into consistent execution.

We are looking for a Chief of Staff who can help us do that better.

Working directly with our CEO and leadership team, you will take responsibility for turning priorities into action, driving important cross-functional initiatives through to delivery and making sure blockers, trade-offs and missed commitments are dealt with rather than allowed to drift.

This is a role for someone who wants to be accountable for outcomes, not just advise on them.

The measure of success is simple: flatfair should execute better, faster and more consistently because you are here, while requiring materially less CEO intervention to make that happen.

The role

You will work across Commercial, Product & Engineering, Customer Operations and Finance on the priorities that matter most to the company.

Some will already have clear owners but need stronger coordination across teams. Others will start as an ambiguous problem, an important decision or an initiative that simply is not moving quickly enough.

Your job will be to create clarity, establish what needs to happen and stay close enough to the work to make sure it gets delivered.

That might mean structuring a problem and recommending a course of action one day, then working directly with teams to unblock implementation the next.

You will also help create a disciplined operating rhythm for the leadership team, so priorities, performance, decisions and risks are visible and commitments are followed through.

A major part of your impact will be increasing the leverage of our CEO: resolving issues at the right level, reducing the amount of coordination and chasing that reaches the CEO, and creating more capacity for strategy, growth, major relationships and leadership.

What you'll do

• Own the execution of high-priority cross-functional initiatives, from initial scoping through to implementation and measurable outcome.

• Turn company priorities into clear plans with outcomes, owners, milestones and measures of success.

• Step directly into delivery when an important initiative needs more structure, momentum or problem-solving.

• Identify dependencies, competing priorities, resource constraints and blockers early, and drive them towards resolution.

• Hold teams and senior stakeholders constructively accountable for agreed commitments.

• Make sure leadership decisions translate into action, with clear ownership and follow-through.

• Help run a disciplined but lightweight leadership cadence across company priorities, OKRs, business reviews and strategic initiatives.

• Give the CEO and leadership team a clear view of progress, risk and the issues that genuinely require intervention.

• Structure difficult decisions using data and commercial judgement, setting out the problem, options, trade-offs and a recommendation.

• Find and deliver practical improvements to how flatfair operates, including simplifying processes and using automation or AI where it creates meaningful value.

What we're looking for

We are much more interested in what you have owned and delivered than your exact job title.

You might already be a Chief of Staff, or you could come from Strategy & Operations, Business Operations, Transformation, Programme Leadership, Corporate Strategy, a CEO or Founder’s Office, or Management Consulting.

Whatever your background, you will need to show that you can move beyond analysis and recommendations into execution.

We would like to hear from you if you have:

• Taken ownership of complex, cross-functional initiatives and delivered measurable outcomes.

• Turned ambiguous problems into clear decisions, plans and action.

• Driven work through to completion when ownership was fragmented or progress had stalled.

• Influenced and challenged senior people without relying on formal authority.

• Used KPIs, financial information and commercial judgement to make better decisions.

• Made difficult prioritisation or resource trade-offs rather than trying to progress everything at once.

• Communicated complex issues clearly enough for senior leaders to make decisions quickly.

• Worked successfully in a fast-moving, scaling or rapidly changing organisation.

You will probably have around 5 to 8+ years of relevant professional experience, but capability matters more to us than tenure.

Experience in SaaS, FinTech, PropTech or another technology-enabled growth business would be useful, but it is not essential.

Practical experience using AI or automation to improve how a business operates would also be valuable. You do not need to be an AI specialist.

Why flatfair?

This role sits close to the decisions shaping the next stage of flatfair and gives you responsibility for helping turn those decisions into results.

You will work directly with the CEO and closely with leaders across the business, with the opportunity to solve difficult problems, improve how we operate and have a visible impact on the pace at which the company moves.

There will be ambiguity, competing priorities and situations where the route forward is not obvious. We are looking for someone whose instinct in those moments is to create clarity, take responsibility and move things forward.

At flatfair, our values are Brave, Connected, Show Up and Welcoming. They matter in how we challenge, collaborate and take responsibility for getting things done.