About Chester

I actually give a damn.
That matters more than you think.

I am not a consultant in the traditional sense. I am an External Strategic Partner — someone who has seen the inside of enterprise, survived the moment that resets all priorities, and built something on their own terms. What I bring to your business is not theory. It is hard-won clarity.

20+
Years in enterprise software & sales
£100M+
In operational leakage identified
MSc
Psychology — understanding how humans create complexity
28%
Survival rate. The number that changed everything.
The story

The day that clarified everything.

I spent my career in corporate roles — chasing the milestones, supporting my family, building something that looked right from the outside. I was good at it. Almost twenty years in enterprise solutions — on-premise, SaaS, cloud, consulting. Rooms full of senior leaders, projects worth hundreds of millions, and teams full of credible, engaging colleagues.

8:35am, 2020

That all changed one morning in 2020. What followed was a major heart attack, two surgeries, and months of recovery. The survival rate for what happened to me is 28%.

What struck me was not the physical recovery — it was the response from those around me. Fresh out of surgery, mid-pandemic with no visitors, just my phone. As I messaged family to let them know I had survived surgery, work called asking for logins; my near-miss was an inconvenience. I was focused on gratitude for being alive, the business was focused on protecting pipeline.

That was the day everything changed.

I resigned with no next step. No safety net. Just a clear decision that I was done building someone else's thing at the cost of my own.

"I realised I actually give a damn about people. About their time. About their wellbeing. I will never be someone who values business over a person's life. We are all replaceable in someone else's spreadsheet. We are not replaceable to the people who love us."

What I built after that is CHESTe. Not out of ambition — out of alignment. I want to use what I genuinely know to help founders who are doing real things and losing real money to problems they can see but cannot quite name.

I completed a Masters in Psychology because I already understood that most operational problems are human problems. Systems do not fail in isolation. People create the complexity, usually without realising it, and usually because nobody has ever mapped the whole thing back to them in plain language.

That is what I do. I map how your business actually flows — and I show you, clearly and honestly, what it is costing you. Then I help you decide what is worth changing. Sometimes old is gold. I will tell you that too.

Background

What I bring to the table.

20+ years in enterprise solutions

On-premise, SaaS, cloud, consulting — I have worked inside the complexity that most consultants advise on from the outside. I know how these systems actually behave, not how they look in a slide deck.

Sales & commercial leadership

Long-cycle, high-value B2B sales across defence, engineering, marine, and technology. I understand how commercial pressure creates process shortcuts — and what those shortcuts ultimately cost.

Psychology MSc

Most operational problems are human problems. Understanding why people create complexity — and how to help them get out of their own way — is as important as any process framework.

Business diagnostics

I have identified operational leakage at scale — including a single project where the cost of misaligned processes exceeded £126 million. The principle is the same at every size.

Fractional & interim leadership

I have stepped into senior roles as an interim strategic partner — providing the external perspective that internal teams cannot give themselves, without the cost or overhead of a full-time hire.

Full NDA confidentiality

My entire professional career has operated under NDA. The founders I work with do not advertise that they needed help. That discretion is part of what I provide — and I take it seriously.

The framework

How I work: ACE.

Every engagement — from a 15-day diagnostic to a six-month partnership — is built on the same three foundations.

A

Accountability

Most founders already know what needs to change. The hard part is owning it. I help people accept the reality of where they are — without judgement, and with complete clarity about what comes next.

C

Clarity

Not the clarity of a nice report. The clarity of knowing — precisely and specifically — what is working, what is not, and what is quietly costing you. Shown back to you in plain language.

E

Enablement

The right decisions become obvious when you can see clearly. I do not tell you what to do. I create the conditions in which you already know — and feel confident enough to act on it.

A note on confidentiality.

I do not have a wall of client logos. I do not have public case studies. That is entirely by design. The founders I work with are dealing with sensitive operational and commercial realities. They did not hire me to become a testimonial. They hired me for clarity — and my discretion is part of that.

If you want to understand the depth of what I have worked on, the best way is a conversation. I will be honest about what I can and cannot share.

Ready to talk to someone who actually gives a damn?

20 minutes. No pitch. Just a straight conversation about whether a Flow Diagnostic makes sense for your business right now.