A private community for badass founders

In today's crowded ecosystem of scammy LinkedIn DMs and sales pitch emails promising instant value-add to your company, it's incredibly refreshing as a founder to have found a resource and community that actually does.

Scot and the Highland team are about as thoughtful as they come, and fill a real gap in serving as a sounding board with tangible tools, templates, and strategies during the scary period that is scaling past $1MM. There's a lot of advice out there to be taken with many grains of salt and a lot of learnings that get gate-kept; that which you get from Highland is genuine, personalized, actionable, flexible, generous, and based on real experiences from really successful — and just plain good — people.

I'd recommend Highland to any CEO looking to expand their network, gut check themselves and their journey, get inspired after a rut, execute on big future goals and projections, or personally grow and develop alongside their company.

Scot and the team at Highland are building a unique experience that's invaluable for any startup founder looking to scale their venture. The content has helped me dial in our operating rhythm, and I've learnt a ton from the community of founders looking to scale their ventures. I wish this resource had existed when I was first starting out! It's an experience that will help you and your business grow.

Joining Highland has been the best thing I’ve done for my personal development in years. I feel like I’m learning so much, so fast, at the moment. Scot’s ability to boil down complex operational theories into simple to understand strategies in the Northstar OS is definitely a superpower of his. We’ve been able to adapt it to suit our business, and for the first time we’re going into the new year with all functions and regions fully aligned. Also it’s pretty cool to be able to just slack someone who’s been through it all before and get an answer immediately. After our conversations, I have such high conviction to be able to drive change in our organization.

I often get invited to join private startup groups and eco-systems, but in all of my years running VC backed companies, the Highland program has delivered the most compelling, unique, and substantive value for me as an entrepreneur and tech CEO. Being able to interact with and learn from some of the leading tech CEOs is invaluable as I build my business, and specifically learning from Scot's experience and his eagerness to help Highland companies is truly remarkable.

The Highland operating system has worked wonders for my team as well and we have all benefited from being a part of the Highland community. If you are a startup founder/CEO and are lucky enough to be asked to join Highland I strongly recommend you do it!

As a first-time CEO & founder, Highland has been extremely valuable for Boost My School in 2 regards - 1) access to growth-stage ops playbooks (e.g. operating cadence, OKR framework, meeting structure) and 2) a community of CEOs at a similar stage of growth. I'd recommend Highland for other CEOs looking to level up and lead their companies in the post PMF phase of growth.

As a first-time CEO & founder, Highland has been extremely valuable for Boost My School in two regards — 1) access to growth-stage ops playbooks (e.g. operating cadence, OKR framework, meeting structure) and 2) a community of CEOs at a similar stage of growth. I'd recommend Highland for other CEOs looking to level up and lead their companies in the post PMF phase of growth.

Learning from someone who has scaled a billion-dollar, values-aligned company has been wildly impactful, but what I love most about this program is the ability to get down to the nitty, gritty of how, when and why! In addition, I've loved having the opportunity to dialog and discuss real-time challenges with Scot and fellow founders at a similar stage.

I've participated in several founder programs, but my favorite part about Highland is the opportunity to include my right-hand woman. For the first time, I'm not the only one on my team hearing valuable information and then trying to put it into action myself.

For founders who have achieved product-market fit, Scot Chisholm's Highland is the single best investment you can make in yourself and your company. Scot shares battle-tested wisdom from his journey scaling Classy to $1B. Through Highland, he gives you the operating system necessary to go from PMF to a successful business that can outlive you.

In a few months, Highland has transformed how I lead — bringing clarity to our mission, values, and goals, and aligning my team around concrete targets. Scot's no-BS mentorship, grounded in empathy for the founder experience, has accelerated my development as a leader.

If you want to level up as a leader, you need to learn from someone who's been there. Scot is that rare mentor who can light the path, push you to grow, and give you the necessary tools to implement what you learn. Sign up for Highland — your future self will thank you.

Learning from someone who's scaled a $1 billion company is a rare opportunity. I've seen how much time and energy Scot has invested in creating something genuinely useful and practical for CEOs and founders to scale their businesses.

He's helped me create systems of unity so that my team spends more time doing the things that move the needle and less time doing busy work.

At any point in your journey, there'll be problems that you can't solve by yourself. Scot's community provides a great environment to learn and continue to build with the guidance of someone who's done it before. Joining the community is a no-brainer.

Working with Scot as my CEO coach through the Highland program, has been pivotal to my growth as a company leader. Scot excels at simplifying highly complex concepts into a simple system, empowering me to enhance my performance and unite our organization around a clear vision. His guidance has been invaluable in my development journey.

I joined Highland as my business entered scale up mode. As a first-time founder, I was looking for a resource to learn how to scale myself alongside my company. What I found at Highland has not only been valuable for myself, but also my team who is learning alongside me. We are getting more focused, more efficient, and more effective from the lessons learned.

What you will find in the Northstar operating system is clarity of purpose for yourself and your team. And you’ll also gain a network of people that simply get it, having been in your seat past and present. If you’re a founder in scale up mode, this is for you.

Highland has become a not-miss meeting. In a relatively short period of time these masterclasses have improved company alignment and clarity on our vision, goals, and objectives. If we hit our stretch goals this year, it will be because of Scot’s playbook.

Highland has by far been one of the best decisions I've made as a CEO. The time to value has been unbelievable. The clarity and alignment we have as a growing startup now that we've implemented the Highland operating system helps me see things more clearly. Scaling feels less impossible, and more inevitable.

Highland is the program that empowers you to translate the theories behind all the great management books into practical, reliable, and steadfast resources. The program focuses on developing your ability to manage, make decisions, and create clarity, focus, and alignment throughout your entire organization by providing you with the tools and knowledge to work smarter.

Scot and his team use real examples and provide valuable and candid insights to help you understand the underpinnings of how each mechanism is supposed to work. They will spend the time answering any questions, deep diving into an issue, and work tirelessly to help you find the right fit for you and your team.

As a CEO and entrepreneur, Highland was the best investment I have made in myself. As a company, it has revolutionized how we approach and do business.

Are you kidding me? Learn from a billion dollar founder & CEO. I'd kill for this earlier in my career.

Last week's class was amazing! Love how the online community is setup too, very positive experience!

Product-market fit is often celebrated as the summit, but experienced founders know it's just basecamp. The real challenge lies in scaling those heights, and that's where Highland has been transformative for us. What sets Highland apart is how Scot and his network of accomplished founders don't just share theoretical knowledge – they guide you through battle-tested methods they've personally used to scale their own companies. Every framework and strategy comes with real-world context and practical wisdom about the pitfalls to avoid. For founders navigating the crucial journey from 10 to 100 million, Highland isn't just another program – it's an investment in developing yourself as a leader who can confidently scale those heights. The methodologies we've implemented have already created tangible improvements in how we operate, and the ability to learn from founders who've successfully made this journey is invaluable. If you're serious about scaling beyond PMF, Highland provides the roadmap, tools, and support system you need to do it right.

I've been loving Highland. Scot and the rest of the crew operate at a super high level, but at the same time, are super down to earth. It's refreshing. A few years back I took my company through a pretty big pivot. We were essentially back in startup mode. Since then, we've grown a lot and mid-2024 I felt like it was time to get some support. Specifically, I wanted proven systems that would help me be the best CEO and set my team up for long-term success. I've been following most of the Highland frameworks to a T and it's helped give myself and my team clarity over our vision and how we're going to reach it.

This year, we set out to scale our business, and Highland was the perfect guide. After 10 months in the program, we now have a clear roadmap and the structure to effectively operate and grow our company. The support system is incredible; we have access to experienced operators and a network of founders who have been through it all. What truly sets Highland apart is the insightful dialogue with fellow founders; the shared knowledge on building a strong company has been invaluable. Highland has been instrumental in our progress, and we're excited for what the future holds. If you're a CEO looking to scale with purpose, direction, and progress, I highly recommend Highland.