Trusted by 2,000+ scaling founders
Become a better CEO. Build a better run company.
Highland Academy Membership gives founders and CEOs the operating system, tools, and templates to build world-class companies, built by Scot Chisholm after scaling Classy from 5 people to $100M+.
👉 Full access. Cancel anytime.
No charge until after the 7 days.
What’s inside a Highland Academy Membership:
Explore the Academy Membership for 7-days, including 20+ Leadership kits, 50+ dashboards and templates, and the complete Northstar OS framework.
The Northstar Operating System
The complete system I used to scale Classy to $100M+. Learn how to create clarity, build rhythm, and scale without chaos.
20+ Masterclass Trainings
Step-by-step videos on every core system: goal setting, dashboards, meetings, compensation, and offsites.
Dashboards & Templates Library
Plug-and-play dashboards, review templates, bonus calculators, financial planning tools, and more.
Guides & Playbooks
Written breakdowns with examples, pitfalls to avoid, and rollout timelines you can follow.
Implementation Roadmap
A clear sequence to install the system in your company, tailored to team size and stage.
1 Year of Access + New Monthly Masterclasses
A new masterclass drops every month so the library grows with you.
Why most companies stall out
Companies rarely implode overnight. They stall quietly, held back by a few silent killers:
-
Confusing priorities scatter focus
-
Meetings drain energy instead of driving action
-
Leaders get dragged into every decision
-
Weak accountability lets things slip
-
Culture fades as headcount grows
These killers burn out founders and stall growth.
Highland Academy fixes them with one company operating system for clarity, rhythm, and alignment. Start your 7-day trial and see how it feels to scale without chaos.
“Highland has been one of the most valuable investments I’ve made. Practical, easy to implement, and designed for busy operators. Since applying the frameworks, my team is more aligned and we’ve already seen real gains in revenue and profitability.”
Academy Membership leaves you systems you can install today
-
1
A clear company Northstar
A focused goal-setting system
-
2
CEO Operating Rhythm Calendar
The meeting cadence, agendas, and decision rituals that keep your team aligned without adding more noise to the calendar.
-
3
Dashboards that show what's really happening
Practical scorecards for tracking performance, surfacing problems early, and giving leaders visibility without constant check-ins.
-
4
Stronger accountability model
Clear roles, owners, standards, and follow-through so priorities don’t disappear between meetings.
-
5
A better way to lead and retain top talent
Frameworks for 1:1s, feedback, performance reviews, compensation, and coaching your best people as the company scales.
Who is this for?
Highland Academy is built for leaders who are scaling fast and need a system that works in the real world.
It’s for you if you are:
- A Founder or CEO who is tired of winging it and wants a repeatable way to scale
- A COO or Head of Ops who needs structure without killing startup speed
- An Executive or Leadership team that needs alignment across departments
- Any Founder-led team crossing 10, 25, or 50 people and hitting management pain for the first time
If you are scaling and don’t want to lose your team or your sanity, this is for you.
“The content has helped me dial in our operating rhythm and I’ve learned a ton from it. I wish this resource existed when I first started out!”
Alexander Olesen
CEO, Buckstop
“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.”
Josh Smith
Managing Director, Me&U
“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.”
Akshay Krishnaiah
CEO, Beem
“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.”
Santhosh Cherian
CEO, Medtrics
…and many more.
Highland Academy's Framework
A note from Scot
Seven years into building Classy, I was nearly fired as CEO. We had hundreds of employees and tens of millions in revenue, but I still wasn’t a great CEO.
I spent the next several years making the real transition from founder to CEO, documenting every lesson, mistake, and framework along the way. Our growth exploded and we set up for the acquisition by GoFundMe.
Biggest lesson = becoming a better CEO was only half the job
I also had to build a company that could operate with clarity, rhythm, and high standards as we scaled.
That is what Academy is designed to help you do.
The CEO Kit taught you the foundations of the role. Academy Membership gives you the complete system for continuing to develop as CEO while architecting a better-run company around you.
Better CEO. Better-run company.
Scot Chisholm
Founder, Highland
Trusted by top founders around the world
Need help with the price?
Try Academy free for 7 days. If it feels right but price is a stretch, email us before day 7 and we’ll do our best to work with you!