CEO & Executive Coaching in Orlando, FL
A CEO Coach Who Has Had Your Job. Already Working With Orlando.
SealShield and Rockway Exhibits + Events are two of the Central Florida companies I’ve worked with, and what their leaders brought into the room looks a lot like what you’re carrying: everything routes through you, the leadership team has titles but you’re still leading their functions, and decisions sit.
Executive coaching for B2B CEOs in Orlando and Central Florida. Weekly, virtual, month to month, and priced on the page.
$3,000/month·Weekly 1-hour sessions·Virtual·Month to month
Orlando has plenty of coaches. Compare records, not websites.
Peer groups, executive coaches, strategy firms: Orlando has them, and some are good. So don’t hire on a website. Hire on a record. Mine: senior leadership at 23. Five companies led across B2B and B2C. Soccer Post from $5.9MM to $15MM in eighteen months, on to $25MM+ and the Franchise 500 three times. NFFS, a construction company, from $7MM to $30MM in three years, Inc. 5000 twice, Best Places to Work.
Since the operator years, 100+ B2B companies advised, from under $1MM to just shy of $1B, Orlando companies among them. If a coach you’re comparing me to has run the stage you’re entering, that’s a fair fight and you should take the meeting. If they’ve only read about it, you already know the difference.
What Orlando CEOs bring into the room
Different industries, same stage. The pattern doesn’t care about the zip code.
- “I’m still the bottleneck.” Decisions pile up on your desk and the company slows the week you’re at the coast. Not a work-ethic problem: your company runs on an operating system that lives in your head. I call it the Invisible Operating System.
- “My leadership team has titles, and I’m still leading their functions.” The tempting diagnosis is talent. Usually it’s structure. Here’s the difference.
- “I promoted my best doers and got my worst managers.” They aren’t failing you. First-time managers land on the wrong side of the line between accountability and policing. That’s Coaching versus Catching.
- “We’re growing and it’s getting harder to run, not easier.” Growth creates complexity faster than capability. That’s the whole thesis, and it’s why the fix is capability, not heroics.
If none of those stung, this isn’t your page. If three did, keep reading.
What you’re paying $3,000 a month for
Not advice. Not a sounding board. A changed CEO.
01
A second operator, weekly
One hour a week, virtual, twelve sessions a quarter. I do my homework between sessions: I know your numbers, your pipeline, the names of your key people. When your org design is broken, it’s our broken org design to fix.
02
Accountability, in writing
Every session ends with a clean list: the deliverable, one owner, a by-when. Every next session starts with a review of the last list. Missed commitments get named, not explained around. Three misses is a pattern, and patterns get named early.
03
Hard truths, delivered with care
If you’re lying to yourself about a co-founder, a market or a hire, you’ll hear it now, not three sessions from now when it’s advice nobody can use. Every hard thing I say comes from wanting you to win. Being nice usually means not telling the truth.
04
Month to month
No annual contract, no exit fee. The work compounds over quarters, but the decision to continue is yours every month. If it stops being the highest-leverage hour in your week, stop.
The full page, including a real session anonymized and the questions you’ll hear in it: Executive Coaching →
In an Orlando leader’s words
“We all benefit from learning from others. Learning and growing with Jerry has been a joyful experience. In my past ~20 years of professional experience, Jerry ranks in the top 5 of my favorite leadership mentors. I am blessed our paths crossed.”
Russell Verhovec · SealShield, Orlando
Two Orlando companies, named
SealShield and Rockway Exhibits + Events. Different industries, the same stage of growth.
Five companies led
$5.9MM to $15MM in 18 months. $7MM to $30MM in three years. Franchise 500 3x, Inc. 5000 2x.
100+ B2B companies advised
From under $1MM to just shy of $1B.
Matt Kleinrock, CEO of Rockway Exhibits + Events, brought a wholly events-based company through the pandemic without losing it. We talked about how on Best Places to Lead: three lessons on resilience →
More proof, and the line between what Jerry ran and what clients changed: Results →
Why an Orlando page for a virtual offer
Sessions are virtual on purpose. The hour should be about your business, not I-4. Virtual is how the hour lands on your calendar every week without fail, and how an Orlando CEO and a Jacksonville CEO end up in the same coaching practice, working the same problems.
But who you hire is still a local decision, and Central Florida’s business community is small enough that a reputation is checkable. Ask around. Then bring your hardest question to the first conversation and judge for yourself.
The full fit test, including who we turn away: Who we work with →
The price, published
$3,000 a month. Weekly one-hour sessions, twelve per quarter, virtual, month to month. Executive coaching runs $3,000 to $10,000 a month across the industry, and most coaches make you get three meetings deep before anyone says a number. I think that’s a tell.
Questions Orlando CEOs ask
Do you coach in person in Orlando?
Weekly sessions are virtual, and that’s a design choice, not a cost cut: the hour stays about the work and never loses to traffic or travel. If you’d rather meet face to face before you decide, say so when you book.
Who is this for?
The CEO of an established B2B company, typically $3M to $9M in revenue that should be $25M, growing faster than the way it’s being run. If you’re pre-revenue or the leadership team is you, this isn’t the right hour yet. The full fit test is here.
How is this different from Vistage, EO or an Orlando peer group?
A peer group gives you perspective. A coach changes how you operate. Both have a place, and I run a room myself, so I wrote an honest comparison with real prices, including the cases where a peer group is the better call.
What does executive coaching cost?
$3,000 a month: weekly one-hour sessions, twelve per quarter, virtual, month to month. No three-meeting dance to get to the number.
I’m in Winter Park, Lake Mary, Kissimmee or Tampa. Same offer?
Same offer, same price. It’s virtual, so the address doesn’t change anything, and Central Florida CEOs share the same labor market, the same customers and the same growing pains.
Two Orlando companies are already on the list. Add yours.
One honest conversation about how your company actually runs. You’ll walk out knowing the blind spots you can’t see from your seat, whether we ever work together or not.
Planning an offsite instead? Strategic planning facilitation for Orlando leadership teams →