Most advisors will give you a framework. A few will give you a process. Almost none will help you see your business — and yourself — more clearly than you currently do.
That clarity is the work.
Enterprise operator and CEO advisor, Kent McKown partners with CEOs when intuition no longer scales and decision quality becomes the constraint.
Kent McKown partners with a small number of CEOs and boards at the point where intuition stops scaling and decision quality becomes the constraint.
There Is a Moment in Every Growing Business When the Rules Change
Not gradually. Not obviously. But unmistakably — if you know what to look for.
The business is still moving. Revenue is up. People are busy. Execution hasn’t broken.
But something has shifted. Decisions feel heavier than they used to. The cost of being wrong stretches further out. What worked through instinct and intensity quietly stops working the same way. You find yourself pushing harder — and getting less for it.
This isn’t a failure of effort or capability. It’s the moment when the entrepreneurial operating system that built the business begins to constrain it. The business has outgrown its leadership architecture — not because the CEO isn’t capable, but because complexity has outpaced clarity. Decisions stop compounding in the right direction. Alignment drifts. The same issues resurface in different forms.
Most CEOs respond by doing more of what worked before. That’s usually what breaks the system next.
This moment doesn’t require more effort. It requires a different level of clarity — about the business, about leadership, and about what the enterprise is actually becoming.
The good news: this moment is navigable. With the right partner, a CEO can slow decisions down without stalling momentum, see the system clearly, and lead in a way that restores coherence and confidence over time.
Why This Perspective
I’ve operated inside this transition myself, more than once — as CEO, CFO, COO, Operating Partner, and Board Member, across founder-led, private equity-backed, and institutionally governed businesses. I’ve led or advised on more than 35 mergers, acquisitions, and ownership transactions, as both principal and advisor, across industries and across the U.S. and Europe.
That range matters less for the breadth of it than for what it makes visible. Sitting in the CFO’s chair changes how you read a CEO’s confidence in a board meeting. Sitting on the other side of the table in 35 transactions changes how you read a deal that’s about to go sideways three months before it does. The pattern recognition isn’t a gift — it’s what three decades of being accountable for real decisions, with real capital at risk, leaves behind.
I’m not a coach, and not a consultant in the traditional sense. I work alongside a CEO or board the way someone who has actually carried the weight of those decisions would — because I have.
The Domains Where Enterprise Value Is Won or Lost
The work typically spans four integrated domains, each one shaping enterprise value in ways that compound over time. These domains are inseparable. Weakness in one eventually erodes the others.
Enterprise Strategy
Clarifying the future state of the business and the value thesis it is building toward.
Financial Discipline
Strengthening margins, working capital, and capital allocation to support resilience and optionality.
Operating Leadership
Establishing cadence, accountability, and decision rights that scale beyond the CEO.
CEO Identity & Presence
How the leader shows up - aligned with what the business now requires, not what worked before.
What This Work Ultimately Creates
Clearer, faster, high-quality decisions
Stronger leadership and operating cadence
Improved cash flow resilience and capital allocation
A CEO who scales as fast as the enterprise does
Who This Is (and Is Not) For
I work with a very small number of CEOs who meet most of the following criteria:
Founder or long-tenured CEO of a business in the $5M–$100M+ revenue range
Leading through scale, professionalization, or ownership transition
Carrying real responsibility for employees, families, investors and lenders.
Navigating complexity across leadership, governance, and capital
Self-aware, reflective, and willing to be challenged
This work is not for:Early-stage startups
Lifestyle businesses without ambition for durability or scale
CEOs seeking tactics, motivation, or accountability alone
How Engagements Work
Engagements are structured around a disciplined cadence, not constant involvement. Most partnerships include:
Monthly CEO sessions focused on enterprise judgment, leadership posture, and decision quality
Periodic deep dives into financial architecture, operating cadence, or leadership structure
Selective ad-hoc access when judgment is needed in real time
The goal is not reliance on an external advisor, but to build internal clarity, confidence, and enduring leadership maturity.
How Engagement’s Begin
Working together typically starts with a conversation, one that’s meant to be useful whether or not we decide to move forward.
1
Request a Private Conversation
If the work described here resonates, the first step is to request a private conversation. This isn’t a pitch or a presentation. It’s a chance to slow things down and talk through what you’re carrying and what has changed in the role.
2
Determine Fit
Not every conversation leads to an engagement, and that’s intentional. We’ll use this time to understand the enterprise, the inflection point you’re navigating, and whether the work I do is actually what’s needed right now.
3
Begin the Work
When there is clear alignment, we move forward deliberately. The work is structured, ongoing, and designed to support better judgment and leadership maturity over time, not quick fixes or surface-level change.