Go from great founder to great CEO
Executive coaching to take you and your company to the next level.
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.
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
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Questions are more powerful than answers.
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Clarity comes from perspective
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Experience is the best teacher
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Accountability drives results
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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:
Client Testimonials
Ben Stephenson
CEO, Impala
RAISED $32M FROM
"Dave is a truly tremendous coach who really helped me through the numerous ups and downs that come with being a Founder who wants to scale. I highly recommend him for his breadth of knowledge and experience and his ability to dig into even the most unfamiliar problems."
Rebecca Kelly
CEO, VenueScanner
RAISED $2.5M FROM
"Dave’s expertise has helped me think through how I communicate with my team, my investors, and other stakeholders in order to really get my message across effectively."
Chris Edson
CEO, Second Nature
RAISED $18M FROM
"The role of CEO is complicated, stressful, and provides very few role models to turn to. Working with someone who is both so knowledgeable on being a CEO and also so empathetic to the strife of building companies is completely game changing for me. My two hours with Dave are the most valuable part of my week. I come out of our sessions invariably energised, with a fresh understanding and clarity on the problems that I brought to the session. I cannot recommend Dave enough."
"Dave’s insightful coaching and powerful questioning helps me achieve clarity of focus—an essential requirement in the startup world. Highly recommended!"
"Dave helped me to explain the value of our proposition which has been a massive support in our fundraising efforts. CEO coaching helps you to clarify what you want from your role and your business and then gives you the strategies to turn this into a reality. I’ve had several new business line ideas which have come directly from our sessions. He is great at encouraging you to clearly articulate your own thoughts and provides accountability and space to think. I would be less effective in my role without him."
"David will be there to prompt you, question your thinking, steer you in directions you may not have pondered, give you insight from the lessons and experiences that have shaped his career, and connect you with his vast network to help unlock problems you are facing."
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.
