CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Every week I tackle management, operations & startup topics that are helping 250,000+ people. Sign up free: www.scotchisholm.com

I also run a leadership accelerator that helps founders develop into top CEOs. Apply here: https://joinhighland.com/apply/

My backstory: 

🚀 Founder of Classy, SaaS for nonprofits raising billions per year

🎗️ Acquired by GoFundMe in ‘22 to create largest giving platform in the world

🌲 Investor in dozens of startups out of family fund, Tall Timbers Holding Co, (Ripple, FanDuel, Hubble, Casetext, etc.)

🏔️ Founder of Highland, leadership accelerator & community for founders

🏡 Co-founder of Haskill Creek, modernized & healthier version of a Walgreens or CVS 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland & food 

⚙️ Industrial engineer & lean six sigma nerd, UMass Amherst grad 

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation

It's been a wild ride. If you're interested in any of the above, please visit my website and reach out to me there. 

www.scotchisholm.com

Scot Chisholm

Getting pushed out of my own company taught me what a CEO actually does...

In 2017, I got called to my lead investor's office in La Jolla.

I waited 30 minutes in the conference room. Then the head of the firm walked in.

"The partners aren't happy with Classy's performance. We think it's time for some change." Two missed quarters. That's all it took.

I had built the company to tens of millions through brute force. But something had gone wrong. Growth slowed. I had become the limiting factor.

I hated them for it. But they weren't wrong.

I was more builder than scaler. More brick layer than architect. It took 24 months to buy them out and get us back on track. Some of the darkest times of my life, but also the deepest reflections.

That experience lit a fire under me to understand the CEO role better than anyone they could bring in to replace me. Not to become the next Jobs or Bezos. But to answer basic questions no one could give me:

What should I be doing all day? What should I focus on? What does a CEO actually do? So I obsessed over studying the best CEOs in the world. What separates the ones who scale from the ones who plateau?

I found that every great CEO masters 7 core responsibilities. I now call them the CEO-7.

I wrote a complete breakdown in yesterday's newsletter. 

If you wanna check it out, I'll drop it in the comments.

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland, Just, Haskill Creek

How defining “great” changed our culture (and decision-making):

A new hire asked me a simple question after onboarding:

“What does great look like here?”

I didn’t have a clean answer.

Not because we lacked ambition, but because we’d never clearly defined it.

Mission, vision, and values weren’t enough.

What we were missing was our perspective on excellence.

That gap pushed us to document our company standards. The non-negotiables that guide decisions when things get messy, fast, or ambiguous. Inspired by how Patagonia articulated its philosophies, we created standards that outlived leadership changes and scaled with the company. 

Here's how I defined them 👇 

***
ps. If you want to read my in-depth article I wrote on this exact topic, I'll drop the link in the comments.

How to define what great looks like:

Here's how to create an unstoppable strategy in 3 simple steps:

First, what is a strategy? Most leaders get this wrong. Strategy is not vision. Strategy is not goals. It's the bridge between the two. Strategy is your unique approach to achieve vision. It shapes your annual goals and daily execution. Vision leads to strategy, which leads to goals.

To create an unstoppable strategy, you need three things:

- Unique approach
- Measurable impact
- Target market

I call this "strategic AIM." A stupidly simple, crystal clear description of strategy that anyone can understand.

1. Approach
What's our unique approach to accomplishing the company's 3 to 5 year vision? Why will people choose us? How are we 10x better than the competition? What are 3 to 5 core bets, multi year initiatives, that we will pursue? Your unique approach creates differentiation at all levels.

2. Impact
What does success look like when we achieve our 3 to 5 year vision? How do we measure it and track along the way? Customer impact, financial impact, shareholder impact. Get crystal clear on what success looks like from day 1.

3. Market
Most leaders target anyone that will buy from them. This is the wrong approach. Instead define exactly who your target market is. Think of it like an archery target. Primary is the inner ring, secondary is the 2nd ring, tertiary is the 3rd ring. Dominate the first before prioritizing the second.

Your strategic AIM informs how you set pricing, packaging, and messaging. It also makes annual goal setting a lot easier. What are the company's top three annual priorities that advance our strategic AIM? Pay special attention to your multi year core bets. These help shape annual goals.

Revisit your strategic AIM at least annually. As your vision evolves, your strategic AIM should evolve. They're joined at the hip. You should always have a company wide strategic AIM, but you could also have one for different products or markets as you get bigger.

If you're a founder or operator and you enjoy my content, you should check out Highland Academy: https://lnkd.in/eAVA5ekz

How to create an unstoppable strategy in 3 simple steps:

In 2017 I was called to my lead investor’s office in La Jolla. 

I had no idea what the meeting was about. 

They wanted me out as CEO after nearly ten years running the company. 

I had missed two quarters and lost their confidence. 

That was enough. 

But they weren’t wrong, I wasn’t yet a great CEO. 

While they tried to push me out, I studied the role like a maniac. 

Determined to be better than anyone that could replace me. 

Ultimately, it worked and the company 5x’d in valuation. 

Now I teach everything I learned through Highland Academy. 

If you’re a founder working to become a great CEO, this is for you.

I'll drop a link in the comments if you want to apply.

Or shoot me a dm.

Don't screw up your annual company kick-off!

Most CEOs don't realize how high-stakes their company kick-off really is. They waste the moment. Why? 

Because they don’t realize how high-stakes it is. They think B- work is ok. Check the box. Get back to the “real work”. I mean, you do have lots of shit going on. Carving out a half-day for a company kick off can feel like a waste of time.

I've been on both sides of this. As a founder, I learned the hard way that the leaders who put their heads down and "get back to work" in January are making one of the costliest mistakes of the year. The annual kick-off isn't a distraction from the real work. It IS the real work.

Andy Grove called this "managerial leverage" in High Output Management. The idea is simple: what you put in is nothing compared to what you get out. A few hours of intentional effort in January can shape the behavior of your entire company for months, if not years. Skip it and you put your team at an information disadvantage you'll be fighting all year long.

The truth is, your kick-off is the highest-leverage meeting of the entire year.
Get it right and your team has the clarity to do their best work all year long. Get it wrong, and you're playing catch-up on culture and alignment for months.

I've worked with hundreds of CEOs on this. The ones who treat their kick-off like the Super Bowl moment it is? They never say die. They show up prepared, energetic, and locked in, and their teams follow suit. The ones who phone it in? They spend the rest of the year wondering why nothing is sticking.

I wrote a guide to follow in a recent newsletter. It includes the one thing your team needs from their leader going into the new year: Purpose, Direction & Progress.

link in the comments to go in depth on this topic 👍

This is where companies quietly fall apart:

Most founders inherit the CEO title before they have any idea what it actually requires. 

You start the company, you get the title. 

No one sits you down and explains what the job is supposed to look like. 

You have to be intentional about learning the role. 

It’s not the same as being a founder. 

Two very different things.

***
Learn what the role of a CEO actually looks like in my recent article (link in comments)

How to speak like the top CEOs on the planet:

Most people communicate: 
- nervousness
- indecision
- selfishness

When they should be conveying: 
- conviction
- thoughtfulness
- partnership

Not all CEOs get it either, but the best certainly do. 

Here’s how 👇 

1/ Keep it clear & simple: Avoid jargon. Use plain English. Be yourself. Don’t over-share or talk in circles. Focus on nailing one main point but never exceed three. Don’t assume understanding. Ask the person if they get it.

2/ Speak with energy: Show enthusiasm & belief in what you say. Avoid fidgeting or whispering. Makes you look nervous. Stay solution-oriented. Don’t be a negative Nancy. You’ll demotivate everyone. Use storytelling to inspire & provide tangible examples.

3/ Talk like a partner: Say “we,” not “I”. Stay relatable to every level of the organization. Create a sense of shared ownership. Ask people: “What do you think?” Take people’s feedback seriously. Even if you make the final call.

4/ Communicate the ‘why’: Tie things back to mission & vision. Always explain reasoning behind major decisions. Help people understand company's progress. Create a sense of urgency when you fall behind. Say “because” more to force yourself to provide context to the team.

5/ Control your emotions: Never let feelings override the message. Stay composed under pressure. Don’t over-share and freak everyone out. But don’t sugarcoat things either. Be realistic & communicate a plan.

6/ Ask the right questions: Don’t pretend to have every answer. Find solutions through thoughtful questions. The best CEOs see themselves as detectives. Practice ‘5 whys’ asking why five times to find root causes.

7/ Guide, don’t dictate: Be a facilitator, not a dictator. Orchestrate debate & discussion. Pre-plan exercises that get people collaborating. Keep the room on track and constructive. Shape the discussion, don’t dominate it.


📌 ps if you want me to teach you how to do this at your company, check out Highland Academy: https://lnkd.in/eAVA5ekz

📌 📌 pps. if you enjoy my content, you'll love my free newsletter. Subscribe here: https://lnkd.in/e6ak5dbP

EOS and OKRs broke at scale. 

Here’s what replaced them.

I spent over a decade building Classy from a scrappy idea into a $100M+ company that processed billions in donations before we sold to GoFundMe.

As we scaled, one problem kept surfacing:
No operating system held up past ~$5M in revenue.

We tried OKRs. The product team loved them. But across the company they became too complex. Too many objectives, too many key results, quarterly resets, confusing grading. The system meant to create focus became a recurring distraction.

We looked at EOS. It was cleaner, but too prescriptive. And I didn’t agree with the idea that the founder should hand off operations to a “professional operator.” 

My belief is simple: The CEO must own the operating system.

There was also a deeper issue.

Classy was an impact company. Our mission wasn’t a slogan on a wall. It was the reason people showed up. We needed an operating system that connected purpose all the way down to daily execution, and not just tactical documentation.

So I built one.

It’s called the Northstar OS.

📌ps. If you want to dive into the Northstar OS framework, check out this article I wrote that breaks it down: https://lnkd.in/eDeRw6D2

pps. Sign up for my free newsletter here: https://lnkd.in/gXCsenmP

"Don't worry, you're gonna do great."

I was frozen in the green room at TEDx San Diego. My body felt like 1,000 pounds. I've only been a founder for a couple of years. Why am I giving a TED talk? People are going to laugh me out of this theatre.

An old man in the corner spoke up. That nudge got my legs working again.

I gave my talk. Came back dripping sweat.

"See, I told you you'd do great. You should be proud."

Then he walked on stage to give his own talk.

⁂

Years later, an advisor sent me a book that changed everything about how I manage people.

The One Minute Manager.

I googled the author. Ken Blanchard.

His face stared back at me.

The old man from my TED talk.

Here was one of the most successful business writers of all time, about to give one of his best talks ever, and he was focused on me.

That night I wrote Ken a thank you. He responded with equal grace.

⁂

The book became required reading for every manager at my company. Here are the 3 lessons that changed how I manage people forever:

1/ Great leadership is a side-by-side relationship. Not top-down. It's a partnership. When the organization wins, the people should win. Get this right and your people start managing themselves.

2/ Catch people doing something right. Positive recognition isn't soft, it's smart. People repeat what's recognized.

3/ Correct the behavior, not the person. Address mistakes quickly and specifically. End with reaffirmation. Every 1×1 becomes an opportunity to help people stay on track.

That night, Ken was demonstrating everything he'd later teach me through his book.

True leadership is the smallest acts of support, delivered at the right moment.

Full story + breakdown here:

Open article: 3 simple rules that changed how I manage people forever: by scotchisholm.com

3 simple rules that changed how I manage people forever:

I write about sales, leadership & productivity to help you become a top sales performer. RSM at Lonestar Forklift | AIB MBA

I’m Chris Crane, and my mission is simple:

Transforming industrial sales reps & teams into formidable professionals.

Over my 15-year sales career, I’ve closed over $100 million in industrial equipment deals, trained more than 150 reps, and led industrial sales teams across Canada and the U.S.

I built the Scaling Success System™ to give industrial sales teams what no one else offers: a sales operating system specifically engineered for industrial sales.

This system has taught over 150+ industrial sales reps & teams to operate as formidable professionals, and it can do the same for your team.

DM "sales" to learn more.

Chris Crane

Most companies hire one kind of rep, and expect them to do both jobs.

They want someone who can hunt.
They want someone who can farm.
They end up with someone who does neither well.

Hunters drive top-of-funnel.
They chase the deal until they get it. 
They don’t stop until the calendar’s full.

Farmers grow existing accounts.
They build solid long-term relationships.
They don’t stop until the client renews again.

Here’s what I’ve learned coaching both:

→ Farmers win with value.
→ Hunters win with volume.
→ Hunters need structure and a clean target list.
→ Farmers need trust  and a relationship to protect.
→ Both lose when you try to make them play the other’s game.

Learning to do both well is an elite level game. 

I have done both, and I can teach someone how to do both, but most companies cannot, and they wonder why they are missing their quotas.


P.S. If you want to turn your industrial sales prospects into buyers, I built a system to show you how 👉https://lnkd.in/dHH93M4u

Experience alone doesn’t scale. A system does. Turn industrial sales prospects into buyers with ARC5™

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Most sales reps consume motivation. Top sales reps study communication.

Everyone wants better closing lines.

Very few reps study the psychology behind why people say yes.

And the gap between those two groups is where commissions are made.

Here are 7 talks every serious salesperson should study.

→ Rejection tolerance — “What I Learned from 100 Days of Rejection” by Jia Jiang

→ Listening discipline — “Want to Help Someone? Shut Up and Listen” by Ernesto Sirolli

→ Persuasion mechanics — “The Four Letter Code to Selling Anything” by Derek Thompson

→ Body language intelligence — “The Power of Nonverbal Communication” by Joe Navarro

→ Conversation control — “How to Have a Good Conversation” by Celeste Headlee

→ Managing resistance — “How to Deal with Difficult People” by Jay Johnson

→ Direct persuasion — “How 5 Simple Words Can Get You What You Want” by Janine Driver

Notice the pattern.

None of them teach scripts.
None of these talks teach product
All of them teach deep human behavior.

Because selling isn’t about explaining your product. It’s about understanding the person sitting across from you.

And the reps who study people always outperform those who study only products.

83% of sales reps run discovery calls with no structure.

They wing it.
They ask surface-level questions.
They pitch before the buyer even admits there’s a problem.

The call feels productive.
The buyer sounds interested.
And then the deal dies quietly two weeks later.

Here’s the 7-step discovery structure most reps skip:

→ Prepare
→ Start Calm
→ Build Rapport
→ Confirm the Agenda
→ Ask & Clarify Pain Points
→ Present Your Crafted Solution
→ Schedule the Next Follow-Up Call

Miss one, and control slips.
Rush one, and urgency disappears.
Ignore the order, and the buyer leads.

The result?

→ Buyers open up faster.
→ Pain becomes specific, measurable, and urgent.
→ Your proposal becomes the logical next step, not a hopeful pitch.

The takeaway:

→ The rep who controls discovery controls the deal.
→ Discovery is not a conversation, it’s a controlled sequence.
→ Structure creates urgency, and urgency creates movement.

Most reps try to close at the end. Elite reps start closing in the first 10 minutes.


P.S. If you want to turn your industrial sales prospects into buyers, I built a system to show you how 👉https://lnkd.in/dHH93M4u

Sales teams don’t fail because of skill.

They fail because they don’t care.
They fail because they’re not engaged.
They fail because they’re disconnected.

Motivation isn’t always about money.

It’s about meaning, mindset & execution.

Here’s what I know:
→ Trust must flow both ways.
→ Goals create clarity & direction.
→ Knowing the “why” drives performance.

Consider this:
→ Start with a 30, 60, 90 plan.
→ Align the team with this objective.
→ Explain the “why” to create full buy in.

Watch what happens with your team in 90 days with full focus on this effort.


P.S. If you want to turn your industrial sales prospects into buyers, I built a system to show you how 👉https://scalingsuccess.co/

71% of sales teams miss quota, and it's not because of effort.

They track revenue.
They track activity volume.
They ignore the indicators that actually drive outcomes.

The dashboard looks full.
The pipeline “feels” healthy.
And the quarter still comes up short.

Here are the KPIs every serious sales leader must track:
→ Key Sales Activity
→ Sales Cycle Length
→ Sales Pipeline Value
→ Average Order Value
→ Product Performance
→ Lead to Opportunity Conversion
→ Opportunity to Sales Conversion

Miss one, and blind spots grow.
Track them inconsistently, and patterns stay hidden.
Obsess over lagging metrics only, and you’ll always react instead of lead.

The result?

→ Forecasting becomes predictable.
→ Coaching becomes precise and data-driven.
→ Revenue stops feeling random and starts compounding.

The takeaway:

→ Activity without conversion tracking is noise.
→ Revenue without pipeline math is guesswork.
→ The leader who tracks the right numbers controls the outcome.

What you measure dictates what your team becomes.


P.S. If you want to turn your industrial sales prospects into buyers, I built a system to show you how 👉https://lnkd.in/dHH93M4u

I almost didn’t call back.

Something felt off.

The buyer sounded polite but distant on the first call.

Most reps would have written the deal off and moved on to the next name in the CRM.

But something didn’t add up.

The problem he described was too operational to ignore.

And when problems are operational, the cost is usually hidden somewhere deeper.

So I called him again.

→ Align: “I understand you’re busy and this might not be top priority right now.”

→ Redirect: “When the system breaks down like you mentioned last week, what usually happens to production that day?”

→ Clarify: “If the line stops for even an hour, what does that actually cost your operation?”

→ Reframe: “So if that downtime keeps happening every week, that’s hundreds of thousands a year lost, correct?”

→ Close: “If we can eliminate that loss, it makes sense to move forward, doesn’t it?”

The result?

→ The problem was bigger than he first admitted.
→ The cost of doing nothing was far worse than the investment required.
→ The deal that almost died on call one closed two weeks later.

The takeaway:

→ Deals rarely die because of rejection.
→ Most deals die because reps accept the first layer of the conversation.
→ The reps who win are the ones willing to dig one level deeper than everyone else.

Most lost deals aren’t lost. They’re just undiscovered.

Most salespeople will never close a seven-figure deal.

They think they can.
They act like they can.
But when the opportunity comes, they choke.

I've seen it firsthand.

I've watched seasoned reps stall.
I've watched managers fumble negotiations.
I've watched buyers walk away, never saying a word.

Here’s what I know:
→ Patience is a strategy. Use it.
→ Big deals don’t die in meetings. They die in silence.
→ If you can’t handle long sales cycles, you won’t survive.

Consider this:
1. Control the frame: If they lead, you’ve already lost.
2. Don't push, pull: Let the buyer convince themselves.
3. Slow down: The bigger the contract, the slower the close.

Big deals are a slow process. Learn to slow down, learn to ask great questions, and the deals will start to come.


P.S. If you want to turn your industrial sales prospects into buyers, I built a system to show you how 👉https://scalingsuccess.co/

Objections don’t kill deals, insecurity does. 

You get pushback.
You lose your composure. 
You spiral into defense mode.

Most reps crumble.

They talk too much.
They try to win the argument.
They forget their job is to lead. 

Here’s what I know:
→ Objections aren’t rejections.
→ They’re tests of your confidence.
→ The buyer is watching how you react.

Consider this:
→ Ask for clarification, find the real fear.
→ Your tone matters more than your answer.
→ Reframe the concern to their original pain.

Master the objection if you want to master the sale. 

Don’t fear them, embrace them.


If you want to turn your industrial sales prospects into buyers, I built a system to show you how 👉https://scalingsuccess.co/

Deals don’t die at the close. They die at discovery.

I learned this the hard way.
Early in my career, I ran a perfect demo.
Clear value, strong interest, confident delivery.

Then the buyer stalled.

“No decision right now.”
And I had nothing to anchor them to.

The problem wasn’t price.
The problem wasn’t timing.
The problem was I didn't equate cost with inaction.

So I rebuilt how I run discovery using CICSR.
→ Context → I force myself to fully understand their current process before touching a problem.
→ Issue → I isolate where the process breaks and make them admit it out loud.
→ Cost → I quantify the damage until the number hurts to say.
→ Solution → I let them describe the future state before I ever show mine.
→ Resistance → I surface hesitation early while I still control the room.

The result?
→ Deals stop stalling.
→ Objections show up earlier and weaker.
→ Buyers convince themselves before I ever ask for the close.

The takeaway:
→ Bad discovery creates fake momentum.
→ Fake momentum collapses at the close.
→ Real discovery makes closing procedural, not emotional.

If you want better closes, stop trying to sound impressive and start forcing clarity.

P.S. If you want to turn your industrial sales prospects into buyers, I built a system to show you how 👉https://scalingsuccess.co/

The deal didn’t die because of price. It died because I skipped one question.

He was engaged.
He liked the numbers.
He nodded the whole meeting.

I thought it was done.
I moved straight to proposal.
I assumed alignment without confirming it.

Two weeks later he said, “We’re going in a different direction.”

Here’s what I missed.

→ I didn’t go deep enough into Context. I understood the surface process, not the internal politics.
→ I uncovered the Issue, but I didn’t press into real Cost with numbers tied to executive pressure.
→ I pitched Solution before asking the Resistance question that would’ve exposed the hidden decision-maker.

So I went back and did it again, the right way.

The result?

→ I quantified cost with his numbers, not mine.
→ I went back and rebuilt discovery from scratch.
→ I uncovered that his CFO had final sign-off and hadn’t seen the math.

The takeaway:

→ If cost isn’t quantified, urgency isn’t real.
→ Surface-level agreement is not commitment.
→ The rep who skips steps pays for it in lost commission.

Discovery isn’t about sounding smart. It’s about controlling the sequence.


P.S. If you want to turn your industrial sales prospects into buyers, I built a system to show you how 👉

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