You did this… but can I get more?

A few weeks back I asked for your feedback.
And boy, did you deliver…

We received dozens and dozens of emails about the new website for Highland, my CEO coaching company. Your feedback also pushed us to rethink how people join Highland in the first place.

If you remember, Highland was having an identity crisis. The business is doing well, but our website still described an earlier version and it was confusing people.

To make matters worse, the CEO coaching and community space is super crowded. You have everything from traditional 1-on-1 executive coaching, to the operating system gurus (EOS, OKRs, etc.), to hundreds of “founder communities” (YPO, Hampton, etc, etc, etc.). Highland combines elements of all three. But when we asked our members what they valued most, the order was clear:

1. CEO Coaching

2. CEO Frameworks

3. CEO Community

Our website had it backwards.

So we started working on new messaging and a new site. We also decided to make “Highland Academy” our consistent public-facing name. I’ll probably always call it “Highland” shorthand, but adding Academy helps people understand it quicker.

Then we shared the early wireframes with you and received mostly positive feedback on the direction, but with lots of great ideas and critique. If I had to boil the feedback down to three main themes, they were:

• Make it crystal clear who it’s for and why

• Better explain what you get with the purchase

• Make it super easy and accessible to get started

Since then we’ve been incorporating your feedback into the polished designs (and I’m excited to share some previews with you below). But that last bullet pushed us to go even further.

When Highland first started, it was me on Zoom doing small group CEO coaching. There was no self-paced version. It was all “live”. We grew it to about 100 companies because that’s all I could handle. Then, in late 2025, we launched the self-paced, content-only version.

The v1 business model was:

• Buy a single Highland Kit ($99-150)

• Go into a 7-day free trial for the whole thing

• Make a purchase at the end of the trial ($1,500 – $2,000)

• Renew annually, and some people upgrade to live coaching

It worked. We grew the self-paced part of the business to $300K in ARR (excluding revenue from single kits — which was mostly a wash with paid ad spend). And this growth fed the live coaching side too.

But your feedback gave us a reason to look at the model again.

For some people, paying a year up front wasn’t a big deal. For others, it was too big of a jump from the single kit.

So, as part of the Highland relaunch, we are simplifying the crap out of the model.

Two simple membership tiers — Self-Paced and Live. And if you choose a Self-Paced membership, you’ll be able to join for only $120/month!

We’re also planning a more guided experience so the content is more digestible. In month 1 you’ll get our core CEO System. That’s PLENTY to work on for the first 30 days. Then in month 2 we’ll unlock more, and so on, until the entire content library is available to you. If you’d rather get everything right away, you can purchase annually like before (but at a new discounted rate).

So, the Highland business model now looks like this:

Free content through social, my personal website and this personal newsletter drives initial interest in Highland. Some will join Highland Academy as Self-Paced members. Some will want live coaching and can apply for the Live membership. And some will just keep reading this free newsletter and be cool with that (also awesome).

Either way, I enjoy sharing how we’re building out Highland (with all the trials and tribulations), and your email replies have genuinely made the business better. Thank you!

Now on to the designs…

* * *

We’re aiming to launch the first phase of the new website by the end of the year. This phase will include a brand new website, new URL (HighlandAcademy.com), new messaging, new membership tiers (discussed above), new Highland-specific blog, and new onboarding into the product itself.

Here’s a sneak peek.

New home page hero:
(Note: the image is really a motion video so you’re only seeing one frame). The home page needs to explain both membership tiers in one unified value statement. You guys gave us lots of great feedback on this. How did we do?

Personal letters throughout:
We use this personal letter format in several places around the site. The goal is to introduce myself, explain Highland, or explain the page or section they just viewed from my personal perspective. We hope it adds a personal touch to the whole thing.

Who’s it for and why:
We think the new site does a much better job explaining who Highland is for and how we help you. We have a page for the Self-Paced membership and for the Live membership. This is the hero section for Live.

Transformation from Builder to Scaler:
This transition from early stage founder to scaling CEO is our sweet spot. There are several sections like this that speak to the transformation we hope you’ll see by joining Highland in either membership tier.

Clearer pricing and comps:
In addition to the membership comparisons, we also show our pricing against other related services. We’re not trying to replace these other offerings, but it’s useful to see the comparison. Highland offers a super affordable entry point to proven coaching and frameworks.

What’s included (Self-Paced vs. Live):
The new site does a better job of explaining what you get as each type of member. This section is from the Live Membership page and talks about that premium offering.

Better testimonials and case studies:
We’ve now worked with (literally) thousands of CEOs, founders and executives, so we have lots of great testimonials and success stories to share.

Highland-specific Content Hub:
Highland’s old website was mainly a sales page. The new website includes a new blog with various content types that we can push out to members. This section, alongside our guest interviews and new ‘Ask Highland’ newsletter, showcases new content monthly.

⁂

Phew! That was a lot. What do you think?

I’d love to get another round of feedback. Just reply to this newsletter. It might take me a second to respond, but I read every one.

In the meantime, we’ll keep plugging away towards launch in December!

Till next time,

Scot

→ scotchisholm.com
→ highlandacademy.com

~~~

P.S. Last week I completely rewrote one of my pillar articles for 2027 (4,000+ words!). I recommend throwing it Speechify, or something like it, and listening to it like an audio book.

What Is Founder Mode?
And How Can CEOs Use It? (updated for 2027)

I hope you like it!

🐐🏔️