Chicago · Twin Cities · Wisconsin
Guiding Founder-Led Businesses to Profitable Prosperity.
More revenue. Stronger margins. A business that runs without you.
Built on Clarity, Alignment, Execution, and Guidance using the Pinnacle Approach™.
WHO WE GUIDE
You’ve built something real. Now, scale it — without burnout, bottlenecks, or the business running you.
We guide founder-led companies to align around a clear vision, install a simple rhythm for execution, and build a business that can grow and run without you at the center of everything — using the Pinnacle Approach™. We work with businesses in Greater Chicago, the Twin Cities, and Wisconsin.
DISCOVER WHERE YOUR BUSINESS STANDS
Most founders have a sense something is off. The Baseline Assessment tells you exactly what — and where to focus next.
In about 9 minutes, you'll evaluate your business across the five Pinnacle Principles — People, Purpose, Playbooks, Performance, and Profit — and receive a personalized report showing where you're strong and where you're exposed.
It's free. And it comes with a complimentary 20-minute call with Keith to walk through your results.
NOT ALL GROWTH IS GOOD GROWTH
On the surface, the business looks strong — revenue is up, the team is busy, and some goals are getting hit. But behind the scenes, you're working harder than ever, profits are thin, accountability is spotty, and the business is too reliant on you.
That’s not real prosperity.
That’s Profitless Prosperity — and it's more common than you think.
At Eskaygee, we help founder-led companies move from Profitless Prosperity to Profitable Prosperity: intentional, healthy, and transferable growth that creates lasting value — for your business, your team, and your future.
PROFITLESS PROSPERITY
⛔️ Revenue is up, but profits are flat
⛔️ You’re the decision bottleneck
⛔️ A-Players burn out or leave
⛔️ Projects stall or drag on
⛔️ Meetings are unproductive or skipped altogether
⛔️ Priorities shift week to week
⛔️ You work in the business, not on it
⛔️ You solve every problem
⛔️ Strategy feels reactive or unclear
⛔️ Can’t step away - the business isn’t transferable
PROFITABLE PROSPERITY
✅ Revenue and profits grow together
✅ Leadership owns decisions and results
✅ A-Players thrive and stay
✅ Goals are clear, projects get done
✅ Meetings are focused and productive
✅ Everyone is aligned on priorities
✅ You lead with vision and space to think
✅ Your team solves problems without you
✅ Strategy drives action and focus
✅ The business is built to scale, transfer, or exit
If you see yourself in the left column, you're not alone.
Eskaygee helps founder-led companies build stronger leadership teams—one decision, one quarter, and one meaningful improvement at a time.
THE PATH TO PROFITABLE PROSPERITY
True prosperity means strong margins, aligned leadership, and a culture built to last. We guide you through a proven rhythm:
🔹 Clarity — Define what matters most and where you’re going
🔹 Alignment — Get your team rowing in the same direction
🔹 Execution — Install the systems and rhythms that drive results
🔹 Guidance — Stay focused, steady, and supported as you scale
WHAT CLIENTS ARE SAYING
Ryan Quinn | President of Quinn Design-Build Inc.
“Keith is our Pinnacle guide and a big part of the foundational success we’ve had at Quinn Design-Build. Keith’s insight, structure, and ability to guide without pressure have been invaluable to us as we’ve navigated ownership, leadership, and long-term planning. He has a gift for meeting business owners exactly where they are and helping bring clarity and alignment to the table—without ever overwhelming the process.”
Tom Grady | CEO of BANLEACO Equipment Finance
“Keith has a knack for cutting through the noise. Through a structured process and PInnacle’s Strategy Builder tool, he guided us toward clearer thinking, better alignment, and practical steps we could act on right away. It wasn’t just a good conversation — it moved us forward.”
Joe Skotarzak | CEO of Big Bumper Company
“Working with Keith through Pinnacle’s Strategy Builder Tool and Strategic Vision & Execution Plan (SVEP) brought real clarity to our strategies, tactics, and direction. The tools were sharp — and Keith’s guidance helped turn good ideas into focused, actionable steps that are moving Big Bumper Company forward.”
“I’ve sat on your side of the table — leading teams, not just advising them.”
MEET KEITH SEEBECK
FOUNDER & CEO, ESKAYGEE | Certified Pinnacle Business Guide
I help founder-led companies build stronger leadership teams through clarity, alignment, disciplined execution, and consistent guidance using the Pinnacle Approach™. The result is a business that grows with greater confidence, stronger leadership capacity, and increasing enterprise value—not greater dependence on the founder.
My background includes executive leadership in investment and finance, commercial construction, IT managed services, and banking. Throughout my career, I've helped organizations implement business operating systems, strengthen accountability, and build high-trust leadership cultures in fast-moving environments.
Today, I bring that experience to founder-led companies. I've sat on your side of the table—leading teams, making difficult decisions, and navigating the challenges that come with growth. My role now is to guide leadership teams in building a simple, repeatable operating rhythm that allows results to compound while complexity gradually fades.
The climb isn't easy. You don't have to make it alone.
ON THE FOUNDER TALK PODCAST
Stop Being the Bottleneck! Build a team that executes, meetings that move the needle, and a rhythm that scales without burning out.