Chief of Staff to the Founder

Meet The Team 👥

This role offers direct involvement in how a company is built and run: the choices about products, people, capital and execution that determine its success.

You’ll work with Barney and the leadership team to investigate difficult questions, develop independent recommendations and turn them into results. Your work might range from diagnosing why a product is underperforming to evaluating a new market, shaping a fundraising narrative or leading a company-wide initiative.

The standard is high. You’ll need to get deep into unfamiliar subjects, interrogate the numbers, challenge assumptions and explain your reasoning clearly. You’ll be expected to contribute your own view and take responsibility for what happens next.

As you build trust and context, you’ll take on greater autonomy, represent Barney in important discussions and own substantial work on his behalf. You’ll see how decisions play out and develop your judgement through direct experience.

For someone who intends to found a company, lead a business or become an investor, this is an opportunity to build the operating experience and commercial judgement to do it well.

About The Role ✍️

We’re hiring a Chief of Staff to partner with our CEO. Working alongside the leadership team, you’ll be the right hand to our CEO, driving the priorities that matter most across Cleo 🌱

• Investigate consequential questions. Analyse markets, products, customer behaviour and business performance. Establish what the evidence says, identify the choices and trade-offs, and make a clear recommendation.

• Own major initiatives. Take priorities off the CEO’s plate and drive them from an ambiguous starting point through to delivery. Work across functions, establish ownership, resolve obstacles and stay accountable for the outcome.

• Improve business performance. Get close to Cleo’s numbers. Identify where results diverge from expectations, work with leaders to understand the causes and help drive a credible response.

• Support fundraising and board decisions. Work with the CEO, Finance and leadership team on rigorous analysis, compelling materials and a clear account of our strategy, performance and capital needs.

• Make leadership time count. Shape discussions around the decisions that matter, prepare useful briefs and follow commitments through to completion. Partner with the CEO’s EA to align his time with his priorities.

• Write and communicate with precision. Produce decision papers, presentations and internal and external communications. Make complex ideas understandable and the reasoning behind recommendations easy to assess.

• Exercise independent judgement. Surface uncomfortable facts, challenge assumptions constructively and explain what would change your view. Build relationships across the business so your recommendations are informed and your work gets done.

What We're Looking For 🕵️

We’re looking for someone with exceptional ability, independent judgement and the ambition to take on consequential work. You may have developed these qualities in strategy, finance, technology, research, entrepreneurship or another demanding field. We’ll assess the quality of your thinking, the difficulty of what you’ve taken on and what you personally achieved.

• A record of exceptional achievement. You’ve distinguished yourself through the quality and impact of your work. You can point to difficult problems you solved, significant responsibility you earned and results you personally delivered. We’ll want to understand your contribution and what made the work demanding.

• Intellectual depth and range. You’ve gone deep in at least one area and can get to grips with unfamiliar subjects quickly. You ask incisive questions, reason from first principles and connect ideas across disciplines.

• Independent judgement. You distinguish evidence from assumption, form a clear view and explain your reasoning. You’re comfortable challenging strong opinions, admitting uncertainty and changing your mind when the facts warrant it.

• Analytical and commercial ability. You’re confident working with numbers, interrogating business performance and evaluating trade-offs. You can turn incomplete information into a sound recommendation and connect detailed analysis to its implications for the company.

• A record of execution. You bring structure to open-ended problems and take ownership through to the outcome. You earn cooperation from strong colleagues, resolve obstacles and follow through without needing to be chased.

• Exceptional communication. You write precise, persuasive prose, listen carefully and make complex ideas clear. You can disagree constructively, earn credibility with senior leaders and represent the CEO’s thinking accurately while contributing your own.

• Ambition, composure and low ego. You seek significant responsibility, welcome direct feedback and hold yourself to a demanding standard. You remain effective under pressure, handle sensitive information with discretion and bring care to both consequential decisions and routine preparation.

• Intelligent use of AI. You actively use AI tools to accelerate research, analysis, writing and execution. You test their outputs and retain responsibility for the quality of your work.

  We welcome unconventional paths and evidence of excellence from different settings. Be ready to show us how you think, what you’ve built or changed, and what you learned from the results.

What you’ll gain
Direct access to the CEO’s thinking, close work with experienced leaders and the opportunity to see your recommendations tested in a real business. Your responsibility will grow as you demonstrate judgement and deliver results.

You’ll develop a practical understanding of how to set direction, allocate resources, evaluate performance and lead through others at a profitable AI company operating at scale.

What we offer

We offer benefits package built to support you in and out of work. Benefits vary by country 🌍 and include meaningful equity, comprehensive health insurance, mental health support, a paid one-month sabbatical after four years, a learning & development platform, pension or retirement contributions, and location-specific leave entitlements.

For the full breakdown on what's available in your location, visit our Candidate Hub 👈