Go from great founder to great CEO

Executive coaching to take you and your company to the next level.

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A startup performs only as well as its CEO.

That’s why top-performing Series A+ CEOs choose Dave Bailey as their executive coach. He helps them by asking the right questions, uncovering new perspectives and holding them accountable for fast and decisive action.

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Dave works with CEOs backed by world-class investors

Reflect on what’s really going on

We know it’s lonely at the top. That’s why every CEO needs a safe place to examine their doubts, reconnect with their purpose and talk through problems in confidence.


Learn with someone who's been there

Dave Bailey has over 10 years of experience in the trenches. Acquire new perspectives and new skills to help you stay in control as your business scales up.


Make better decisions faster

Good decisions come from a clear mind. Work on the tough questions, choose clarity over certainty, and be held accountable for getting stuff done.


Core beliefs

  1. Questions are more powerful than answers. 
  2. Clarity comes from perspective
  3. Experience is the best teacher
  4. Accountability drives results
  5. Great leaders embrace vulnerability


Dave's Credentials

Co-founded several companies (successes and failures)

Raised millions in angel and venture capital

Hired and managed hundreds of employees

Over 10 years of operating experience in the trenches

Invested in multiple startups with Downing Ventures


Worked as a Programmer, Product Manager & Marketer

Mentored hundreds of startups via Google ’s accelerator

Writes for several high-profile tech publications

Certified Agile Scrum Master / Product Owner

Graduate of Oxford University and Stanford Business School

Who is right for CEO Coaching?

CEO Coaching is for ambitious high-performing entrepreneurs that:

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Client Testimonials


Become the CEO your company deserves

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Frequently Asked Questions

You’ll receive deep coaching sessions every two weeks to work through the issues most important to you. You’ll also receive feedback and tailored training on the areas that you want to develop.

Yes. Clients receive 24/7 phone support for those moments when you need it most.

Of course! Everything we talk about in a coaching session is strictly confidential and between only you and your coach.

The best CEOs have a natural curiosity, a strong desire to improve, and the ability to communicate effectively. If you also have an open mind for new ideas, and the humility to admit that there is always room to grow (even after you know it all), then you’re coachable!

CEO coaching is highly affordable for late Seed and Series-A+ venture-backed startups. Even if you're pre-revenue or just starting out, one-on-one coaching might still be more cost-effective than you think.

CEO coaching is typically a business expense, paid for by the company.

Your company wins or loses based on the quality of its leadership. Taking better decisions earlier will save you months of wasted effort and cost. We estimate a return on investment of between 7X and 50X.

Working with an external coach allows you to fully explore your doubts and share ideas openly in ways that are hard to achieve with your co-founders and board.

Investors are investing in you. They want CEOs who are clear, confident and self-aware. Investing in yourself is completely aligned with your investors’ goals.

No, we specialise in, and work exclusively with, founder CEOs, concentrating on the specific challenges and opportunities that are unique to this role.

Stop putting it off. Get a coach.

Inquire about CEO Coaching

Inquire about CEO coaching

Dave takes on a limited number of scale up CEOs each year. To inquire, please, fill in the form below.