Break the dependency your business has on you.
Leadership coaching for the people at the top of a scaling business.
to a successful exit.
Gerry Tombs, Leadership CoachYou’re the bottleneck, and you know it.
“Everything routes back to me.”
“I still can’t switch off on holiday.”
“If I step away, progress slows down or stops altogether.”
If you stepped away for two weeks, what would happen?
For most founders and their COO, the honest answer is: things would slow down, or stop. Decisions stack up waiting for you. The team is good, but they’re a set of functional heads, not a leadership team that can run the business without you in the room.
You’re growing, which should feel like winning. Instead it feels like more chaos, more reactive decisions, more of you holding it together by sheer hours. You can’t switch off on holiday. Every hard call still gets routed back to you or your COO to referee.
That dependency has a cost. It shows up in growth, and it shows up in value, most clearly in the areas below.
I’ve seen this in leadership team after leadership team. Good people, real effort, and still every decision waits on the founder. Fixing this is the whole job.
Who I am and why I coach.
I started Clearvision in a garage in Southampton in 1997. Over the next 25 years it grew into a software tooling consultancy working with the likes of Procter & Gamble, Royal Bank of Scotland, and Vodafone, eventually reaching around 100 people across the UK and US. I ran the business on Scaling Up and EOS, real operating systems, not theory, and used them to build a culture that held up under scrutiny.
Clearvision climbed the UK’s Best Companies to Work For list year after year, from around 96th on first entry to #9, and finally to #1 in 2022. That ranking is the clearest proof the culture was real, not a slide in a deck.
In October 2022, I sold Clearvision to a Finland-based DevOps company. The deal closed with 98% of the price paid up front, which only happens when the buyer isn’t pricing in founder-dependency. I’d spent years deliberately making myself scarce, handing over relationships and decisions, so the business could run without me. By the time we sold, it did.
I know first-hand what a good coach is worth. Even with a leadership team I trusted completely, I always wanted someone impartial outside the room, no skin in the game, to think things through with. That’s what coaching CEOs and COOs now lets me pass on.
I’m Hampshire-based. Since selling Clearvision I’ve founded AgentimiseAI, helping founder-led SMEs use AI properly, and built GuidanceAI, a digital coaching tool that gives leaders access to their coach’s thinking between sessions.
Areas of Experience
Leadership challenges
- Founder and leadership-team dependency: delegation, decision rights, removing yourself as the bottleneck
- Leadership team design: the right seats, clear scorecards, peer accountability
- Operating rhythm: weekly meetings, a simple prioritisation filter, every leader owning a number
- Cash discipline: building a cash fortress, not running deal to deal
- Culture and hiring: values-based hiring that holds up when the founder isn’t in the room
Preparing for exit or a major event
- Exit-readiness coaching from someone who has actually sold, on strong terms
- Building a business a buyer will pay full price for, because it doesn’t depend on you
AI in leadership roles
- Where AI genuinely creates leverage, not where it just adds noise
- Practical, current guidance from someone building AI systems for SMEs right now
Most coaches stop at the CEO. I don’t.
The usual model is one coach, one relationship, filtered entirely through the top of the org chart. Everything the CEO learns has to be re-taught, second-hand, to the rest of the leadership team, if it reaches them at all.
- Coaching stops at the CEO’s office door.
- The rest of the leadership team leads without a coach, and without the thinking behind the CEO’s decisions.
- What the CEO learns in a session has to be relayed, imperfectly, weeks later, if it’s relayed at all.
- I put a digital version of myself, built on my own thinking and methodology, in reach of the whole leadership team.
- 24/7 access, so a functional head can think something through the same day it comes up, not next month.
- Everyone benefits from a coach, not just the person at the top.
What working together looks like.
This isn’t generic executive coaching. It’s built around the two people at the top, coached individually and together, though single-leader coaching is available too if that’s a better fit right now.
Start with a conversation
A free 30-minute introductory call. No pitch, no pressure. Just a conversation to see if this is the right fit, for both of us.
Book a call→See it in action
A 2 hour workshop with you and your COO together. £300. Not a sales pitch dressed up as a workshop, but real work on your business, so you experience how the coaching actually operates before committing to anything ongoing. If the workshop doesn’t give at least one concrete thing to act on, it’s free.
The ongoing partnership
A monthly retainer, built around a consistent cadence:
- A monthly 1:1 with the CEO
- A monthly 1:1 with the COO
- A monthly 2:1 session with both of you together
- Ongoing support between sessions, calls and WhatsApp access
- 24/7 access to a digital coach built on my own thinking and methodology
- Optional: Gerry sits in on a monthly leadership session (L10) with your wider team
Give this three months, and most CEOs notice the same thing: fewer small decisions land on their desk, because the team’s finally making the calls that were always meant to be theirs.
In their words.
Since meeting Gerry in 2023, my career has been on a challenging, intense, and at times overwhelming journey — but one that has been transformative in all the right ways. Gerry has been there throughout: offering business guidance, reassurance, and perspective, but also supporting me as a person.
What sets Gerry apart is the combination of real-world experience, structured thinking, and deep emotional intelligence. His knowledge is rooted in decades of building, leading, and scaling businesses, yet he brings it with a humility and clarity that make it instantly practical. He has a passion for process and a systematic approach that helps turn complexity into focus and action.
Perhaps most importantly, Gerry doesn’t shy away from telling you what you need to hear. He’ll call you out on your own bull….(blind spots), challenge your assumptions, and push you to grow — always with the intent to help you become a better version of yourself. Working with him has been one of the most valuable experiences of my professional life.
Who this is for, and who it isn’t.
This isn’t for everyone, and I’d rather tell you that now than waste your time.
- A founder-led business, roughly £4m–£100m in revenue.
- A CEO and a COO (or a clear operational number two) at the top.
- Growing, and feeling the drag of founder-dependency.
- Genuinely willing to delegate and let go. That’s the work.
- Wants a coach to think with, not a consultant to execute for you.
- Pre-revenue or under £4m — no COO yet, and likely not the budget. Too early.
- A large corporate over £100m — management layers, not founder-dependency.
- A solo founder with no number two — the dual model won’t apply (single-leader coaching still can).
- Anyone wanting done-for-you consulting or a quick fix. I coach, I don’t execute.
- A business in decline or needing a turnaround — that’s a restructuring specialist.
How much does this cost?+
The workshop is £300. The ongoing monthly retainer is £900 a month, on a three-month minimum commitment with one month’s notice after that. It covers everything in the offer above: individual sessions, joint sessions, between-session access, and a digital coach. We’ll talk specifics on the intro call.
Why only five clients?+
Because this only works with real attention. Five CEO and COO pairings is the most I can properly hold in my head at once. More than that, and something slips.
Is this therapy, or business coaching?+
Business coaching. We’re fixing decision rights, delegation, and the operating rhythm of your company.
What if my COO and I aren’t on the same page about needing this?+
That’s common, and it’s usually worth exploring on its own. The free 30-minute call is a good place to start, even if only one of you is convinced right now.
Do you work outside the south coast?+
The model works fully online. South coast is where I’m based and where in-person sessions are easiest, but plenty of the work happens over video and async either way.
Do I need to be running Scaling Up or EOS already?+
No. I coach from having run both, but plenty of clients aren’t on either system yet. We build what your business actually needs.
Start with a conversation.
I work with a maximum of five CEO and COO pairings at any one time. This means I’m never spread too thin to notice what actually matters in your business. When there’s room, there’s room. No countdown clocks, no false urgency.
Let’s have a conversation, view my calendar for availability.