Become the CEO
your company needs.
You don't need an MBA, consultants, or years of screw ups to scale from $1M to $100M+ in revenue. Get the exact CEO system Scot used at Classy to scale into the hundreds of millions.
Go from builder to scaler
trusted by 5,000+ scaling founders
Topics covering goals, meetings, workplace culture, finance, goals, etc.
How to manage people, how to build a bonus plan, CEO priorities advisor, and more.
Attend virtual Fireside Chats with well-known operators
Members get exclusive access to every new Kit developed by Scot
Join 5,000+ CEOs building better companies
“We’ve used a number of frameworks in the past, such as EOS and OKRs. But none of them provided the guidance and tools at a practical level like this. As a founder & CEO, I found Highland to be exceptionally useful and would highly recommend it.”
“Scot’s ability to boil down complex operational theories into simple strategies is a superpower. For the first time we’re going into the new year with all functions and regions fully aligned.”
“Highland isn’t just another program. It’s an investment in developing yourself as a leader who can confidently scale. The methodologies have already created tangible improvements in how we operate.”
“In a few months, Highland has transformed how I lead. It has brought clarity to our mission, values, and goals, and aligned my team around concrete targets.”
“The content has helped me dial in our operating rhythm and l’ve learned a ton from it. I wish this resource existed when I first started out.”
“The content has been critical for my team’s alignment. We now have a language and a system for operating that everyone understands from the leadership team all the way down.”
Elite CEO coaching, without the elite price.
Highland's coaching and frameworks are from operators that have scaled real companies to $100 million and beyond. Not from consultants that have never actually done the thing.
Elite-level coaching. Now accessible to any leader.
I'm not a coach who read about this. I lived it.
I’m a 4x founder. I built Classy from a pub crawl fundraiser into a $100M+ company that was acquired by GoFundMe in 2022.
In 2017 my lead investor tried to replace me as CEO. And honestly? In that moment I wasn’t sure he was wrong. I had been leading on instinct for years and it stopped working.
I made a decision. I was going to become a better CEO than anyone they could bring in to replace me. I became obsessed with one question: what do the best CEOs in the world actually do?
What I found was that every great CEO masters seven core responsibilities. Not traits or personality types. An actual job description. Clear, learnable, and executable.
The investor who wanted me gone? We bought him out. We 5x’d our valuation and sold to GoFundMe. No founder should have to almost lose their company to learn this. That’s why I built this kit.
Never say die. 🏴☠️
Not another "course" platform
Highland gives you the tools for continuous growth in the CEO role.
- AI Coaching Assistants
- CEO System Templates
- Members-Only Deep Dives
- Member-Only Newsletter - Where we answer CEO questions you questions you can't ask ChatGPT or Claude.
