People
“I can’t find good people, and I can’t keep the ones I’ve got.”
The #1 challenge for small and midsize CEOs. 67% call hiring a major challenge, 62% retention.
Jeff Jackson
Certified EOS Implementer®
Somewhere along the way, the business started running you.
I help owners of privately held companies, 10 to 250 people, get clear, get aligned, and get the business running without them. You're not alone. 76% of owners say the same. And it doesn't have to stay this way.
No pitch. A real conversation to see if we fit. If we do, your leadership team gets 90 minutes with me, on me.
Where the line runs
The vision
Where you are going, agreed
The execution
Tools and disciplines that stick
The people
Clarity, courage, gratitude. Where we focus hardest
True
What owners tell me on the first call
You're not the only one carrying this.
Owners of privately held companies, 10 to 250 people, tell me the same things no matter the industry. Good people are hard to find and harder to keep. Growth has stalled. Profits are shrinking. The business depends on you, and 3 out of 4 of you lose more sleep over it than over anything at home. The research says the same thing my 60+ clients have: industry changes the vocabulary, not the issues.
Profit
“Revenue’s fine. So why isn’t the money there?”
62% of CEOs expect revenue to grow this year. Only 47% expect profit to improve.
Process
“Everything depends on somebody remembering how it’s done. Usually me.”
Only 37% of Boomer owners, and 59% of Gen X, are very confident their team could run the company without them.
Growth
“We hit a ceiling and I can’t see why.”
49% of midsize leaders name uncertainty their top challenge. CEO confidence is down three straight quarters.
All-consuming
“I can’t step away. The business owns me.”
77% of owners made personal sacrifices last year. 1 in 5 doesn’t take a full day off a week.
Alone with it
“Nobody around me gets what this is like.”
76% of owners lose more sleep over the business than over anything at home. Half of CEOs report loneliness, and 61% of those say it hurts their performance.
You led it here. You can lead it out. All of it is fixable.
I give business leaders their lives back. Work you love, with people you love, a business that makes great money and does good in the world, and time left over for everything else you're passionate about. The Entrepreneurial Operating System® gives us the tools. The work is helping you and your team use them, and clearing whatever is keeping you from leading the way you want to.
Start with a 30-minute call- of owners lose more sleep over the business than over anything at home
- 76%of owners lose more sleep over the business than over anything at home
- expect revenue to grow / expect profit to improve
- 62% / 47%expect revenue to grow / expect profit to improve
- challenge for small and midsize CEOs: finding and keeping good people
- #1challenge for small and midsize CEOs: finding and keeping good people
Sources: Vistage CEO Confidence Index Q3 2026 · Gallagher 2026 Survey of Business Owners · NAPEO · JPMorgan 2026 Business Leaders Outlook · Exit Planning Institute 2025 · Bluevine 2026 · RHR International
Stories of changed lives
Don't take my word for it.
The business is the vehicle. The owner getting their life back is the point. Two weeks off and never checking email. That's what done looks like.
“We were stuck. Jeff helped us align our leadership team, get focused, and start solving real issues, fast. He guided, challenged, and coached us into becoming a healthier leadership team.”
Chris Torrioni
President, Sensible Micro
“Jeff helped us simplify everything. The meetings, the language, the structure. It all just clicked. We had the right people, but no system to bring them together.”
Chase Carpenter
President, H&S Companies
“Jeff gave us tools we didn’t even know we needed, and showed us how to actually use them. Our leadership team was aligned, focused, and having the right conversations for the first time in years.”
Will Young
CEO, Aerowave Technologies
- full-day sessions
- 360+full-day sessionsin the room with leadership teams, teaching them to see clearly, decide, and execute
- companies
- 60+companiesdozens of industries, every size, one job: help them see what’s true and act on it
- as an operator
- 30 yrsas an operatorevery seat, every function. I don’t teach anything I haven’t had to do myself.
A selection of my clients
How it starts
Three steps. No pressure.
My guarantee
I provide value in every session, or you don't pay for it.
The first 90 minutes are free, no strings. And once we book your first full day, every session after it carries the same promise: if you don't get value, that session is free. I've never had to honor it. I'd rather you know it's there.
- 1
30 minutes, you and me
A call to see if we fit. You tell me what’s going on. I tell you how I work, who should be in the room next, and what to expect. No slides.
Request the call → - 2
90 minutes with your leadership team
Once we’ve talked, I come to you. I show your whole team how I work and what “done” looks like at the end of the journey I take with all my clients. On me. You keep what you learn either way.
- 3
You decide
If it’s a yes, we book your first full day. If it’s a no, we shake hands and I’m still a phone call away.
Who I work with
Owners and leadership teams of privately held companies (non-profits too), typically 10 to 250 people, who are coachable, abundance minded, and great to be around.
You love learning and you want to grow, personally and in the business. You don't take yourself too seriously. Any industry. If you've got humans, I can help. Who you are matters more than how big you are.
Probably not a fit
If you're not coachable, I can't help you, and I'll say so on the first call. If you lead with negativity, we'll both be miserable.
Where I'm taking new clients
- Central Florida · within about three hours of my session room in Clearwater
- West Michigan · I'm there regularly
- Virtual, anywhere · companies that are remote, or want to run the whole thing 100% virtually
What I do
Two ways in.
One practice, one way of working, one goal. Stories of changed lives. Find the one that fits where you are, and come join me.
Primary
EOS® Implementation
Owners of privately held companies, 10 to 250 people · Central Florida, West Michigan, or fully virtual
I help leadership teams implement EOS, the Entrepreneurial Operating System®, as a Certified EOS Implementer®. Everything about that work lives on my EOS Worldwide page.
Every 90 days
Owner Roundtable
Twelve seats. Business leaders only.
A room of business leaders around a table in Clearwater for two hours. We walk the six things every company runs on, Vision, People, Data, Issues, Process, and Traction®, and where companies get stuck in each. Then we stop talking and put a real issue through the IDS® process, live. Somebody brings a genuine problem from their business and we work it in front of everybody. Then we solve a few more at our tables.
Next: Tue 12/1, 7:30 breakfast · 8-10a · Clearwater
Also
Two more rooms I host
ENRG, Clearwater chapter · monthly, free
A help-first community for business leaders. Ninety minutes a month: a short teaching segment, then the room works through the real issues members bring. Say it "energy."
Join the Clearwater chapter →Advisor Roundtable · every other month
For the people who advise owners: fractional CFOs, CMOs, bankers, attorneys, brokers. Bring the client issue you're stuck on and leave with a next step.
Ask about the next one →
Who's behind it
Jeff Jackson
Certified EOS Implementer®
Recovering President and CFO
MBA, University of Florida
Lean Six Sigma Black Belt
Among many things, I'm a recovering CFO. For 30 years I ran and fixed businesses from the inside: President and CFO of private equity-owned and family-owned companies, interim CFO brought in to get companies back on their feet, consultant to PE firms and their portfolio companies, and an operator inside everything from pre-revenue startups to multinational, multi-billion-dollar businesses, worldwide. Today I'm a Certified EOS Implementer®, and that work has its own home on my EOS Worldwide page.
Along the way I've led or advised every function a company has. Marketing, sales, operations, customer service, manufacturing, professional services, IT, finance. M&A, from due diligence through integration. Business process redesign, lean enterprise, Lean Six Sigma. Dozens of industries. I've mentored founders in university and chamber of commerce accelerators and incubators. There isn't much I haven't seen, and very little that surprises me anymore. That's the part owners find useful.
I help leadership teams get crystal clear on where they're going and put the discipline in place to actually execute it. But the tools alone don't change a business. The people do. So all along the way, I help the people running the company get out of their own heads, let go of what isn't true, and lead from a place of clarity, courage, and gratitude. That's where I focus hardest.
Relationship comes before results. And the results will come.
The one question
Does it ring true?
Where the line runs
A plumb line doesn't argue. It just shows you where true is. That's what I listen for in every session: the place a team has drifted from its true line. It usually shows up in the language first. “If” instead of “when.” Doubt dressed up as prudence. A limiting belief nobody has questioned in years. So we get the strategy straight, build the muscle to execute it, and work on the people the whole way through. Clear the drift, and the line holds.
The vision
Where are you actually going, and does everyone in the room agree? Most teams think they do. Ten minutes in, they find out. This is where we start.
The execution
Do you have the tools and disciplines to get there, or just good intentions and a long to-do list? What gets planned, gets done. Period.
The people
Is the owner leading from clarity, courage, and gratitude, or from the stuff rattling around in their head at 2am? The business follows its people. Every time.
Let's talk.
Everything starts with a 30-minute call. Tell me a little about what's going on and how I can best serve you, and I'll reply within one business day with a couple of dates and times for us to meet.
972-743-0069 · jeff.jackson@eosworldwide.com