Dave Bailey

CEO coaching · Series A–D

Most CEO coaches bring good questions. I bring a leadership system.

CEO coaching for founders of venture-backed tech companies, built by someone who has been one. You get world-class coaching and a system of 500+ frameworks developed with 250+ CEOs.

A high-level summary of my coaching methodology

See how I coach.

I work exclusively with CEOs of post-product-market-fit tech companies, Series A to D. Earlier than that? Start with the essays, and the coaching will be here when you get there.

The system

If you want to scale, you need a system.

1

Build your CEO plan

Clarify the few priorities that will make the biggest difference, turn them into quarterly outcomes, and create real accountability around them.

2

Apply high-leverage tools

Use proven frameworks to solve predictable scaling challenges faster, from team structure and strategy to delegation and time.

3

Get world-class coaching

Reach out when a difficult decision or unexpected issue arises, and get responsive support exactly when you need it.

The work

What we’ll work on together.

Twelve areas, each with proprietary frameworks from the system.

Reimagine Your Role

Elevate yourself out of the details and redesign your role around the work only you can do.

Proprietary frameworks+
Role Reset™Calendar Upgrade™CEO Decision Matrix™CEO Game Plan™Founder Mode Foundations™

Streamline Your Meetings

Build a simple meeting system that creates alignment, improves decisions, and gets the best from your team.

Proprietary frameworks+
Meetings OS™The Offsite Builder™Better Board Blueprint™The Facilitators Playbook™The Thinking Meeting™

Boost Your Energy

Protect your energy, play to your strengths, and remove the physical, emotional, and operational drains that hold you back.

Proprietary frameworks+
Founder Needs™Personal Advantage™Courageous Conversations™Narrative Work™Beating Resistance™

Tell Powerful Stories

Turn your vision into compelling stories that inspire belief, shape your category, and attract attention.

Proprietary frameworks+
The Vision Verse™The Storyteller’s Playbook™The Category Leader™The Founder Brand Formula™

Strengthen Your Strategy

Create a sharper strategy by clarifying your customer, positioning, capabilities, and sources of competitive advantage.

Proprietary frameworks+
Need Narrative™The Strategy Summary™Achieving the Impossible™Shapes of Strategy™The Power Brainstorm™

Inspire Alignment

Give your team the context, expectations, and accountability they need to act with speed and commitment.

Proprietary frameworks+
Relationship Design™The Accountability Checkup™The Contracting Conversation™Mastery Transfer™The Delegation Brief™

Leverage Your Talent

Build a high-performing team by hiring the right leaders, clarifying expectations, and acting decisively when someone is not working out.

Proprietary frameworks+
The CEO Support Stack™The A-Player Audit™Serious About Talent™The Right Hire™The Startup Leadership Map™

Coach for Performance

Help your leaders think better, take ownership, and improve their performance through practical coaching conversations.

Proprietary frameworks+
Relationship Design™Coaching Foundations™The Faster Coaching Method™Powerful Questions™The Decision Toolkit™S*** Swapping™

Shape Your Culture

Turn the behaviours and mindsets you expect into practical systems that shape how people work, even when you are not in the room.

Proprietary frameworks+
The Mindset Filter™The Culture Campaign™Agile Performance Management™Leading with Love™The Round Robin Retro™The Change Maker™

Accelerate Growth

Build repeatable growth engines, align the company around what drives progress, and expand into new markets with confidence.

Proprietary frameworks+
Achieving the Impossible™The Launch Engine™The Profitability Hotseat™

Raise Capital

Create a compelling pitch, run a disciplined fundraising process, and maintain the mindset needed to keep momentum.

Proprietary frameworks+
The Perfect Pitch™The FOMO Formula™The Winner’s Mindset™

Master M&A

Build the knowledge and negotiating skills to buy or sell companies while protecting value and creating strong outcomes.

Proprietary frameworks+
The M&A Accelerator™The Negotiation Canvas™The Acquisition Playbook™
Fit

How to know if we’re a fit.

This is for you if…

  • You are the CEO of your company
  • Your company is post-product-market fit, Series A–D
  • You like a structured, results-focused approach
  • You decide fast and act on what we discuss
  • You believe investing in yourself has a huge return

It isn’t if…

  • You’re a CTO, COO, or investor
  • You’re pre-product-market fit or pre-revenue
  • You want on-demand hand-holding
  • You’re looking for life coaching or therapy
  • You believe the problem is everyone else
Dave Bailey
In your corner, quarter after quarter
Results

What clients say about the results.

Anastasia Leng
Anastasia LengCEO, CreativeX · Raised $30M+

I'll readily admit I was a coaching skeptic when we started, but I couldn't be more of a "fan girl" today. My sessions with Dave give me clarity, focus, and a roadmap to being a better CEO and a better leader.

Paul Ebert
Paul EbertCEO, Tabeo · Raised £750M+ (debt)

I am a better CEO thanks to Dave. Ultimately, the feedback I receive from my family, investors, and teams makes me greatly value his work.

Alan Jiang
Alan JiangCEO, Beam · Raised $135M+

Dave has been an incredible coach to work with. He has a way of asking questions to dig to the core of challenges, suggesting solutions, and also getting actionable commits that drive real change.

Jose Lorenzo
Jose LorenzoCEO, Bold · Raised $120M+

What I like the most about working with Dave, is the fact that he has been an entrepreneur himself and he speaks not only from theory but from practice.

Tim Heyl
Tim HeylCEO, Homeward · Raised $296M+

Coaching with Dave has transformed the way I show up as a leader in my business. Dave has a unique ability to uncover what's important with insanely good questions. I highly recommend all startup CEOs work with Dave.

Mikela Druckman
Mikela DruckmanCEO, Greyparrot · Raised $58.3M+

Being a founder is learning by doing but without reflection there is little to learn. Dave is exceptionally good at framing issues in a way that helps you to move forward and grow the company.

Questions CEOs ask
What’s the difference between an executive coach and a CEO coach for founders? +

Executive coaching was built for managers in stable corporations. Founder-CEO coaching addresses the job of running a venture-backed tech company you started: the pace, the board, the fundraising, the identity. I've only ever coached CEOs, and I've been one.

How is this different from other CEO coaches? +

Most coaches bring questions. I bring questions plus a system: 500+ frameworks and playbooks built over eight years coaching 250+ venture-backed CEOs. You leave every session with something you can run with your team the same week.

What stage of company do you work with? +

Post-product-market fit, roughly Series A to Series D, with teams from 20 to 1,500 people. Earlier than that, start with the essays. They'll serve you until the coaching fits.

How much does CEO coaching cost? +

I work with a small number of venture-backed CEOs on long-term engagements. Terms are shared privately with CEOs exploring fit. The first step is a short conversation.

What results should I expect? +

Faster, more confident decisions. A leadership team that executes without you in every room. And a version of the CEO role you actually want to do for the next decade.

Ready to talk?

Tell me about your company. If it looks like a fit, we'll find a time to speak.