Ops Articles & Business Operations Insights – Scot Chisholm

Scot Chisholm

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Highland Academy
Highland Society
JustClaims
Haskill Creek
GoFundMe

Popular Articles

What a CEO Actually Does: 7 Essential Responsibilities
Are Leaders Born or Made? Evidence from 20 Years of Leading Teams
How to Create a Company Vision
The Perfect Bonus Plan for Any Company (updated for 2026)

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Culture

How to Create a Company Vision
5 Rules of Giving Feedback
7 Company Culture Killers and What to Do About Them
10 Ingredients of a High-Performance Culture
How to Create Company Values
Fix the 5 Dysfunctions of a Team
How to Write a Great Mission Statement

Founders

The PDP Leadership Framework: 3 Questions Every CEO Must Answer
The Perfect Bonus Plan for Any Company (updated for 2026)
The Business Operating System That Replaced EOS and OKRs at My Company
What a CEO Actually Does: 7 Essential Responsibilities
Why I Started Highland: A CEO Coaching Program for Founders (and their teams)
Are Leaders Born or Made? Evidence from 20 Years of Leading Teams
How to Create a Company Vision
Three Rules for Early-Stage Startups
5 Rules to Master Delegation
Founder Mode: What It Actually Means
5 Calendar Rules Every Leader Should Follow
Top 10 Lies Startup Investors Tell
7 Startup Mistakes That Kill Companies
7 Mistakes Raising $200M
The Ideal Founder Compensation Package
How to Create Company Values
7 Critical Lessons for New Startup Founders
How to Write a Great Mission Statement
10 Worst Pieces of Startup Advice
Top 7 Startup Founder Mistakes

Leadership

The PDP Leadership Framework: 3 Questions Every CEO Must Answer
Test Your Leadership Skills: A 3-minute PDP self-assessment
The WhyGo Framework: An OKR Alternative
How to Crush Your 1-on-1 Meetings (updated for 2026)
The Perfect Bonus Plan for Any Company (updated for 2026)
Resilience for Leaders: The #1 Predictor of Success (and how to build it)
The Business Operating System That Replaced EOS and OKRs at My Company
What a CEO Actually Does: 7 Essential Responsibilities
Why I Started Highland: A CEO Coaching Program for Founders (and their teams)
Are Leaders Born or Made? Evidence from 20 Years of Leading Teams
5 Rules to Master Delegation
How to Run the Perfect Leadership Meeting
The Annual Performance Review Is Dead
7 Reasons You’re Losing Your Top Performers
How to Resolve Conflict as a Manager
12 Habits to Become a High-Performing Manager
Top Interview Questions to Hire
Meetings Suck (Here Are the Only 3 You Need)
Fix the 5 Dysfunctions of a Team
10 Worst Pieces of Startup Advice

Management

Test Your Leadership Skills: A 3-minute PDP self-assessment
The WhyGo Framework: An OKR Alternative
How to Crush Your 1-on-1 Meetings (updated for 2026)
Resilience for Leaders: The #1 Predictor of Success (and how to build it)
7 Essential Rules For Setting Business Goals
5 Rules to Master Delegation
5 Rules of Giving Feedback
How to Run the Perfect Leadership Meeting
The Annual Performance Review Is Dead
7 Reasons You’re Losing Your Top Performers
How to Resolve Conflict as a Manager
12 Habits to Become a High-Performing Manager
Top Interview Questions to Hire
Meetings Suck (Here Are the Only 3 You Need)

Ops

The WhyGo Framework: An OKR Alternative
How to Crush Your 1-on-1 Meetings (updated for 2026)
7 Essential Rules For Setting Business Goals
How to Build a Financial Plan for a Startup Business
Three Rules for Early-Stage Startups
5 Calendar Rules Every Leader Should Follow
7 Startup Mistakes That Kill Companies
Meetings Suck (Here Are the Only 3 You Need)
Fix the 5 Dysfunctions of a Team

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Leadership,Culture,Ops / December 1, 2023

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Welcome, friend!

I’m Scot, multi-time founder, investor and industrial engineer by trade. I started a company called Classy, a SaaS platform used by over 10,000 nonprofits to raise money and manage their fundraising. In 2022 we were acquired by GoFundMe and together the companies have raised over $40 billion for individual and nonprofit causes. More recently I founded Highland Academy, a leadership program and community for founders transitioning into world-class CEOs.

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Frequently
Asked Questions

Who is Scot Chisholm?

Hey, thanks for asking. First, I’m a human, just like you (hopefully). Second, I’m a proud dad and husband. Third, I’m a multi-time founder, investor and (originally trained as) an industrial and mechanical engineer. I started a company called Classy at 25, with my friends and roommates in San Diego, CA. We grew it pretty big over the next 10+ years, and sold it to GoFundMe in 2022. Now I write a lot, teach founders in Highland, and help manage several businesses across our family’s portfolio. I recommend signing up for my free newsletter and if you want to work with me directly, check out Highland Academy.

What companies has Scot Chisholm founded?

Classy is the company I’m best known for (at least in nonprofit and tech circles). Classy was acquired by GoFundMe in 2022, and they rebranded the company to GoFundMe Pro. I founded Highland in 2024, a leadership program and community for founders transitioning into world-class CEOs. I also co-founded Just Holdings (first brand launched is JustClaims) with Chris Himes in 2025, an AI-powered platform that helps property owners navigate insurance claims. Lastly I co-founded a few local businesses in Whitefish, Montana, including Haskill Creek — a reinvention of the traditional drug store — with my wife Carrie, high school friend Craig McViney and early employee Colette Stroia.  

What is Highland by Scot Chisholm?

Highland is a leadership program and community for founders, CEOs and high-level operators that I founded in 2024. It has two parts:

Highland Academy is a self-paced online “school” for founders, CEOs, and high-level executives scaling businesses from $1 to $100M+.
Highland Society is an exclusive community of 150 or fewer founders & CEOs (and their leadership teams) that includes live training, events, and peer support. Society members span the US and beyond.

Why did Scot Chisholm start Highland?

Back in 2017, I lived the nightmare most founders fear most: being pushed out of my own company by my lead investor. I got us far on brute force, but I wasn’t yet a great CEO. I was more builder than scaler. More brick layer than architect. The experience was painful, but it lit a fire under me to understand the role of CEO better than anyone they could possibly bring in to replace me. I studied the best, took what worked, threw out what didn’t. And I made a promise to myself that if we were lucky enough to survive the ordeal (we did!) and have a great exit (we did!), I would share everything I learned with others going through the same scaling challenges.

What is the Northstar Operating System (NOS) by Scot Chisholm?

The Northstar Operating System (NOS) is a business operating system I developed while scaling Classy, and now teach to thousands of founders, CEOs and operators through Highland. I was frustrated by existing systems (EOS, OKRs, etc.) that were breaking down on our way to $100M+. I purposefully designed it to remove organizational complexity and create extreme alignment across my team. It’s built on three core pillars: Operating Clarity, Operating Rhythm and Operating Standards. You can learn more about it on my blog and at Highland Academy.

What companies has Scot Chisholm invested in?

I invest across software, AI and sports through our family fund, Tall Timbers Holding Co. Some of our investments include CaseText (acquired for $650M), Ripple, FanDuel (acquired for $11.2 billion), Hubble and Albion Soccer Club.

What is Scot Chisholm’s affiliation with Albion Soccer Club?

Albion Soccer Club holds a special place in my heart. My son first started playing for the club at 4 or 5 years old in San Diego. I became friends, and then business partners with long-time CEO Noah Gins. Our investment (through our family fund, Tall Timbers Holding Co.) helped kick start Albion’s national expansion around 2016. I continue to serve on the Board of Directors today and play an active role as a board member and close adviser.

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Scot Chisholm

Articles
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CEO Coaching
Highland
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Current Projects

Highland Academy
Highland Society
JustClaims
Haskill Creek
GoFundMe

Popular Articles

What a CEO Actually Does: 7 Essential Responsibilities
Are Leaders Born or Made? Evidence from 20 Years of Leading Teams
How to Create a Company Vision
The Perfect Bonus Plan for Any Company (updated for 2026)

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