How we fixed a positioning problem that capped our growth:

My company (Highland) has a problem I’m trying to fix.

Let me tell you about it, then I’ll show you the wireframes.

Highland started as small group CEO coaching. Every Wednesday I’d get on Zoom with ten founders and go through a different CEO topic – from alignment to accountability to attitude.

Why “founder community” was the wrong position.

It kept growing. So we started calling it a “founder community” (instead of CEO coaching) to better represent what it had become. We opened up a Slack channel for all the CEOs to connect with each other, gave them access to all my coaching content through Circle, and created an annual event on our farm here in Whitefish called Highland Workshops.

Highland 1.0 grew to about 70 unique companies (~100 core members when you count co-founders). We charged anywhere from $250-$1,000 per month to start, which got us to about $200k-$300k ARR. Enough to pay our tiny team of two a decent salary (excluding myself). But not enough to get excited about as a business.

And the growth was hard. Our first 10-20 CEOs found us because they already knew me (or Classy). This created a false confidence. Once I hit about 20 CEOs, I realized, rather humbly, that every new member would need some convincing. So I hired Fletcher to run sales and account management. We did outbound through LinkedIn, Instagram and email, but our hit rate was laughable.

This wasn’t Fletch’s fault. Highland had a positioning problem.

By calling ourselves a “founder community” we were getting grouped in with Hampton, YPO and EO (not to mention the thousands of other online communities that popped up like weeds from 2022 to 2024). Most of these communities focus on maximizing member-interactions. That was the value.

But that’s not what we were building at Highland. And it’s not how our members stack ranked the value once they were in the door. Here’s what they found most valuable:

1. CEO coaching

2. CEO systems

3. Community

Community was the cherry on top, not the core product. Yet we were leading with “community” and not “CEO coaching” or “CEO systems”.

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Making Highland Scalable

The other major problem was how heavy the model was. If CEO coaching was the product, and I was the one delivering it, the business had a natural ceiling (before I went clinically insane). Filling my schedule with 1×1 coaching meetings sounds like torture. Then, when you factor in new curriculum, guest interviews (we call them Firesides) and Workshops, it starts to add up fast.

So I gave myself a hard constraint. Three hours of live coaching per week, plus async conversations on Slack with our members. I had to make the business work around this, or I was probably going to shut it down. I quickly realized that with just me and a three-hour window, I had a hard cap around 100 members. And we were there already.

So around that same time, in the least splashy way ever, we launched Highland Academy, our new self-paced portal with all my coaching and systems pre-loaded in it. Call it Highland 2.0.

This test wasn’t cheap (around $150K all-in with design and development). But it solved our biggest issue. Highland could scale beyond 100 members. Now, any CEO, founder, business owner, executive, or manager could sign up for Highland, access pre-recorded CEO coaching and templated systems, without needing me to deliver anything live.

But would they?

We priced it at $2,000 per year (whereas the live version of Highland is around $12,000 per year, depending on company size). Still, compared to normal CEO or executive coaching, which usually costs anywhere between $60k to $180k per year, both options are a bargain.

The good news was pricing wasn’t the issue. The bad news was people weren’t fully biting on the Academy.

* * *

Repositioning Highland

There are a lot of great executive coaches out there. But here’s the reality: most have never actually been a CEO before. That isn’t necessarily a deal breaker. Coaches can add value in ways that don’t require CEO experience. But as my Highland members have told me, it’s exceedingly rare to find a coach who’s actually been in the seat before, at their stage and beyond.

But why?

Well, it’s simple. Most proven founders don’t dream about becoming a CEO coach after they exit. I certainly didn’t. I stumbled into this space after doing a favor for one of my investors (advising one of his portfolio company CEOs). I joke that I’m the only fucking idiot who still talks about all-hands and 1×1 meetings AFTER selling their company.

The more I thought about it though, that joke was actually the insight. We needed to lean into my experience leading Classy as its CEO for nearly two decades.

First, we had positioned ourselves as a community and walked right into a bloody red ocean. All our energy was spent explaining why this wasn’t like those other communities you already know. That’s a terrible place to be.

Second, after we launched Highland Academy, we made the mistake of broadening our message in paid ads. We did this because (technically) more people could sign up for Highland now. But all this did was muddy the water.

Then we started telling my actual story…

I was a founder struggling with the exact same things that you are. In fact, I almost got pushed out of my own company because I couldn’t figure out how to transition from founder to proper CEO. But once I did, I recorded every mistake, lesson and framework that helped me scale the company into the many hundreds of millions in value.

This new positioning started working. Highland was now CEO coaching + CEO systems, for CEOs running companies between $1M and $100M, built off the back of my operating experience, and the experience of other operators I bring into the program.

“CEO coaching by actual CEOs” is the position.

Highland Academy started growing. We’ve now had over 250 CEOs sign up for the annual recurring plan (without talking to a sales person). This is on top of the live coaching members (Highland 1.0) which stayed capped. Together they bumped our ARR to $600K-$700K with clear line of sight to $1M+.

Now this was getting interesting.

* * *

New website wireframes

That brings us full circle to the Highland website, which hasn’t changed since 2024. It still says “founder community” right on there. And on the Academy page we bolted on afterwards, it speaks too broadly to leaders and operators, not the CEO going through the same thing I did.

So for the last few weeks I’ve been working hard on wireframes for a new site, with this new positioning we’ve been testing through paid ads.

Here are a few shots (note: this is pre-design and purposefully black & white):

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What I’d love your feedback on

I’d genuinely love your feedback on the new positioning. Especially if you’re a founder and CEO.

Looking at the wireframes, is it clear what Highland does and who it’s for?

Shoot me an email and let me know HERE

Till next time,

Never say die 🏴‍☠️

Scot

→ scotchisholm.com
→ highlandacademy.com

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P.S. I’m super excited for this new website, but it’s only the beginning for Highland. The future involves building a product on top of this mountain of coaching and frameworks. I’ll write about it more in the future.

Onward.

🐐🏔️