Shawn Freeman

Technology Coach & Founder | Proven technology leadership to help you grow a profitable future proof business.

You’re not just running an MSP. You’re building something bigger. 

But right now, it feels like you’re stuck working in the business instead of leading it.

You’re juggling too many roles, managing clients, fixing daily issues, and trying to grow your monthly recurring revenue. The competition is fierce, and figuring out how to break through feels overwhelming.

I get it because I’ve been exactly where you are.

In 2011, I founded my own MSP. It started small, with all the typical struggles. Feeling trapped in the day-to-day grind, pricing uncertainty, struggling to delegate effectively, and the constant stress of finding quality clients. But through relentless refinement of systems, positioning, and leadership strategies, I scaled that MSP to seven figures. In 2020, I successfully exited with a high-value acquisition.

Now, as the founder of Impactful MSP, I help ambitious MSP owners like you achieve sustainable, long-term growth, without burning out or getting lost in the weeds.

👉 Here’s the truth:
Your technical skills aren’t the problem. The real challenge is building a business that runs profitably, consistently, and without you trapped in the day-to-day grind.

You don’t need random tactics or one-size-fits-all frameworks.

You need proven strategies, clarity, and the right mentorship to:
✅ Define a mission, vision, and core values that guide every decision you make.
✅ Scale your MRR fast with systems that work, no fluff.
✅ Stand out in a crowded MSP space with a unique differentiator.
✅ Attract and retain high-value clients who pay what you're worth.
✅ Simplify operations so you stop being the bottleneck.

You know you're capable of more, but you're unsure of the next step.

That's why you need me:
I've lived the MSP journey. I’ve felt the stress of unpredictable revenue, tough client churn, competing in a saturated market, and the struggle to lead while overwhelmed. But I also cracked the code to breaking through, and I’ve helped MSPs scale to seven figures and beyond using my coaching methods.

My clients have:
→ Increased MRR by 25%+ within months.
→ Closed larger, more profitable deals with ideal clients.
→ Built scalable systems that run without micromanagement.

This isn’t theory. It’s battle-tested strategy from someone who’s been in the trenches.

If you're serious about becoming the go-to MSP in your market and ready for predictable, scalable growth, send me a DM with the word 'IMPACT' and let’s talk about your next level.

No fluff. No hype. No BS. Just results.

Vice President - Alberta

I saw this meme and laughed a little too hard.
Because if you run an MSP, you’ve lived this.

When everything works, the question is,
“Do we even need IT?”

When one thing breaks, it becomes,
“Why are we paying for IT?”

That reaction is normal.
And it’s also something you can mostly prevent.

Here’s how:

First, meet with your clients a few times a year.
Not to review tickets, but to talk about their business
and what’s actually happening in their environment.

Second, make the invisible work visible.
Show what you’ve been monitoring, preventing,
and quietly keeping off their plate.

Third, translate that work into business outcomes.
Instead of tools and acronyms, explain what it meant
for uptime, risk, productivity, and their team’s day.

Fourth, have real strategy conversations.
Ask where they’re stuck, what’s slowing them down,
and offer clear suggestions to fix those problems.

That’s when clients stop seeing IT as a cost
and start seeing you as part of the business.

And yes, some clients still won’t engage, meet,
or act on recommendations no matter what you do.

That’s usually a fit issue, not a service issue.

Not every client is right for a proactive MSP.
And it’s okay to offboard the ones who aren’t.

If you’re running into this with clients, DM me.
I’m happy to help you navigate those conversations.

I help MSP Founders Build and Scale Outstanding IT Companies (just like I did - using proven systems with actual long term results)

Stop lowering your prices. Start raising your standards.

They said, “Your price is too high.” and you hesitated.

We’ve all been there.

That sinking moment when doubt creeps in:
→ “Am I asking too much?”
→ “Should I lower my price?”

Every time you discount, you’re not just lowering price.
You’re lowering the belief in your value.

The clients who demand discounts often:
→ Micromanage your process.
→ Undermine your expertise.
→ Expect the world, but pay for peanuts.

And they rarely stay satisfied.

Contrast that with your best clients:
→ They don’t choose you because you’re cheap.
→ They choose you because you deliver.

Because the right clients don’t see price as a hurdle.
They see it as a reflection of your worth.

So why do we feel the need to discount?
It’s simple: We fear losing the opportunity.

But saying yes to the wrong clients
means saying no to your best work.

Your value isn’t for everyone and that’s okay.

You’re not competing to be the cheapest.
You’re striving to be the most impactful.

How do you stand firm on your pricing?

1. Focus on outcomes, not deliverables.
• Clients pay for results, not for tasks.
• Be the solution to their biggest challenges.

2. Pre-qualify clients upfront.
• Communicate your value clearly.
• If they can’t see it, they’re not your client.

3. Embrace the power of saying no.
• It’s not rejection, it’s alignment.
• Your time is too valuable to spend on the wrong fit.

The next time someone asks you to lower your prices
say this instead: “I focus on delivering results that last.
That’s why I don’t cut corners, or prices.”

Because great clients don’t go for the cheapest option.
They go for the best.

Shoutout Case Kenny for the quote!

Entrepreneurship isn’t about avoiding failure.
It’s about learning how to get back up.

You’ve faced challenges most people walk away from.
But you didn’t. You stayed in it.
And that’s what makes you an entrepreneur.

Success doesn’t follow a clear path.
It’s not something you plan step by step.

There are detours, slow days, and a lot of uncertainty.
But if you’re still showing up, you’re on track.

This video nails the reality of entrepreneurship:

Fail fast. Fail hard. Fail often.
↳ But always get back up.
↳ Every failure teaches you a lesson.

Setbacks don’t mean you’re off track.
↳ They show you what’s not working.
↳ So you can figure out what does.

Progress isn’t loud.
↳ It shows up in small steps and quiet wins.
↳ But all of it stacks up over time.

Resilience is what matters.
↳ You don't have to be perfect all the time.
↳ Just willing to come back better than before.

So remember: You’re not failing. You’re figuring it out.

Because entrepreneurship isn’t a talent.
It’s a skill you build, one lesson at a time.

Learn, adjust, then try again.
That's how you win.

👇 What’s one thing failure taught you?
♻ Repost to remind someone they’re not alone in this.

Sometimes there’s nothing to do but monitor.

Happy Friday MSPs!

If your business can’t run without you, you don’t really
have a business... you have a very demanding job.

A lot of owners don’t realize this until they step away.
They take a few days off and everything backs up.

Not because the team is lazy.
Because you’re the default answer.

Something comes up and the instinct is to come to you.
→ Not to think it through.
→ Not to try to solve it.
→ Just to ask.

Over time, that creates dependency.
And most of the time, it’s unintentional.

If the answer always comes from you,
your team never learns how to figure it out.

Part of growing a business is changing that dynamic.

Your team needs space to think.
Space to decide.
Space to get it wrong and learn.

One of the most effective things I did was simple:

I took real vacations and made myself unavailable.
→ Not as a test.
→ Not as a stunt.
→ Just as a boundary.

And something interesting happened.

Problems still came up.
But the team figured them out.

They rented tools.
They made calls.
They solved things without me.

Before that, they would’ve just waited.

That’s when you know things are shifting.
When the business keeps moving without you.

Being able to step away and come back
to a functioning business is real freedom.

If everything stops when you’re not available,
and your business is too dependent on you, DM me!

Episode four of Beyond Technology is now live!

This episode is about the work behind great stories.

My guest is Aidan Campbell, co-founder and CEO of
2C Media Inc., a studio focused on long-form storytelling.

Aidan helped build 2C Media into a trusted partner for
organizations that care about meaning, trust, and craft.

We talk about how storytelling evolves alongside media
and technology without losing its human core.

Aidan shares lessons from building resilient systems,
navigating real technology failures, and balancing
efficiency with creativity behind the scenes.

We also explore how tools can support people instead
of replacing them, and why trust and collaboration
matter so much in creative and leadership work.

Thank you Aidan for joining me for this episode.

And thank you Entrepreneurs'​ Organization Calgary
and 2C Media Inc. for helping bring this podcast to life.

You can watch the episode on our YouTube channel
or listen on your preferred podcast platform.

Links to both are in the comments.

If you are or know a strong Calgary leader who should
be a guest on the podcast next season, send me a DM.

New episodes drop every second Monday.

I hope you enjoy S1 EP4: “Aidan Campbell: How
Storytelling Stays Human as Media Evolves.”

Big goals are easier to achieve than small ones.

Let me explain why.

Small goals feel safe, attainable, and realistic.
But big goals do something small goals can’t.
They give you room to adjust.

When the vision is big, you don’t rely on a perfect plan.
You think creatively, look for help and try different paths.

When something doesn’t work, you don’t quit.
You adapt and stay in the game.

You know where you want to go, you’re just
figuring out the best way to get there.

Failure isn’t fatal, but failure to try again is.

There’s a quote I love that says,
“You didn’t fail. You fell. As long as you get up, you win.”

That’s what big goals give you.
And that’s how real growth happens.

You set the destination and keep trying until you win.

If you have big goals for your MSP in 2026
and aren’t sure where to start, send me a DM.

I’d be happy to help you map the way forward.

The most important shift in entrepreneurship is
moving from short-term planning to long-term thinking.

Not because short-term goals are wrong, but because
long-term goals change how you operate day to day.

With a longer horizon, there’s less pressure
to force every decision to work immediately.

Instead of locking yourself into a single path,
you give the business room to iterate and evolve.

You can test ideas, reroute when things aren't working,
and make decisions based on direction, not urgency.

I’ve seen this make a real difference as companies grow.

Teams become less reactive.
Conversations get clearer.
Progress becomes more intentional.

I talked about this with Jeff Humphreys
on Episode 185 of The Calgary Sessions.

We also discuss:
→ Acting before everything feels certain
→ Building businesses around trust and relationships
→ Paying attention when something feels off
→ Measuring success by impact, not just numbers
→ Designing companies to last

Huge thanks to Jeff for having me on!
Links to the full episode are in the comments.

Most MSPs don’t have a lead problem.
They have a referral problem.

Not even a lack of referrals,
but a lack of intention behind them.

Great referrals don’t come from asking harder.
They come from building a business worth talking about.

When clients clearly understand your value,
they introduce you to people like them.

Those leads are different.

They’re already qualified.
They trust you before the first call.
They close faster and stay longer.
And they’re usually clients you enjoy working with.

That doesn’t happen by accident.

It comes from clear positioning, clear outcomes,
and a client experience designed for the right intros.

That’s what my referral engine is built around.

I broke this entire process down into a full course
inside Empath, based on how I’ve actually scaled.

And inside my coaching, we tailor it further, so it fits
your business, goals, and the clients you want more of.

No ads.
No cold calls.
No chasing bad fits.

If you want better clients and a referral engine
that runs on trust, send me a DM.

Your MSA is more than a legal document.

Done right, it protects trust, profit, and growth.

It defines how you work, how you charge,
and how your team delivers consistently.

So it shouldn’t be something you sign once
and forget about until there’s a problem.

A great MSA should:
→ Protect your margins and set clear limits.
→ Renew automatically without yearly re-signs.
→ Include built-in rate or cost adjustments.
→ Use clear, simple language wherever possible.

If you already have one, review it carefully.
Look for anything that causes confusion or slows deals.

Does it reflect how you actually operate today?
Does it hold up when scope or pricing changes?

If you’re starting from scratch, begin with structure.
I built a customizable MSA template for MSPs.

A clear MSA does more than protect you.
It makes working with clients smoother for everyone.

No surprises, no second-guessing, no chasing scope.

Delivery runs cleaner.
Client conversations get simpler.
And your team stops needing you to step in.

If you’d like my MSA template, DM me.

If “busy” is your default state, that’s a red flag.

In almost every conversation I have with MSP owners,
how busy they are comes up within the first few minutes.

Long days, constant questions, and everything feeling
urgent usually point to the same underlying issue...

Too many decisions, problems, and priorities still flow
through the owner instead of the team handling them.

As the business grows, your role has to evolve with it,
otherwise the business never really scales past you.

You’re not there to personally solve problems anymore.
You’re there to make sure they get solved without you.

That shift starts with how you spend your time and
what work you continue to hold onto by default.

Less jumping in to fix issues as they appear,
more helping your team think through them properly.

Less answering questions reactively throughout the day,
more defining outcomes, ownership, and boundaries.

When those things aren’t clear, everything escalates
upward to you, whether you like it or not.

Not because your team is incapable or unmotivated,
but because the system trained them to rely on you.

That’s when being “busy” stops being temporary
and starts becoming the permanent operating mode.

The goal isn’t to disappear from the business entirely.
It’s to create enough space to actually lead it well.

Space to think strategically about where you’re going.
Space to build relationships that matter long term.
Space to plan beyond today’s problems and fires.

That space doesn’t come from working harder or longer.
It comes from structure, clarity, and real delegation.

This is the shift I focus on inside my coaching programs,
helping owners delegate without losing control.

If being busy feels like your baseline right now,
DM me and let’s talk through what needs to change.

12 CRM Features Every MSP Should Be Using

Most MSPs only use about 20% of their CRM.
The rest collects dust while the team stays busy.

No automation.
No reporting.
No real visibility.

If you’re just logging deals and updating notes,
you’re not using a CRM, you’re tracking data.

A CRM should simplify your world, not add work.
It should automate follow-ups, renewals, and reminders.
It should give you clarity on pipeline, profit, and priorities.

That’s why HubSpot is my go-to for most MSPs.
It’s simple to run, but powerful when it’s built right.

Here are the 12 CRM features MSPs should be using:

→ Deals and Products
→ Custom Properties
→ Contact Management
→ Sales Pipelines
→ Service Tickets
→ Meeting Scheduler
→ Reporting Dashboard
→ Marketing Automation
→ Live Chat and Bots
→ Tasks and Follow-Ups
→ Email Logging and Templates
→ Workflows and Sequences

I put all of this into a one-page cheat sheet.

If you already use HubSpot, this shows you
how to turn it into an actual growth engine.

If you don’t, it’s a quick look at what’s possible
when systems actually work together.

You don’t need another tool to scale.
You just need to unlock the one you already have.

Grab the cheat sheet below and put it to use.

Build the system once.
Let it run every day after that.

Episode five of Beyond Technology is now live!

This episode is about putting people first,
with technology working quietly in the background.

My guest is Paula Worthington, founder
and president of Worthington PR & Story.

Paula has spent more than 20 years helping brands
communicate with clarity, trust, and intention.

We talk about why strong relationships stay central
to great communication as technology evolves.

Paula shares how her team balances personal service
with efficiency, and how they decide when people lead
and when tools step in to support the work.

We also explore adapting to new platforms,
using tech intentionally, and building client trust.

Thank you Paula for joining me for this episode.

And thank you Entrepreneurs'​ Organization Calgary
and 2C Media Inc. for helping bring this to life.

You can watch the episode on our YouTube channel
or listen on your preferred podcast platform.

Links to both are in the comments.

If you are or know a strong Calgary leader who should
be a guest on the podcast next season, send me a DM.

New episodes will drop every second Monday.
Excited to keep sharing these conversations with you.

I hope you enjoy S1 EP5: “Paula Worthington: How to
Prioritize Relationships and Use Technology as Support.”

Going into 2026, I’ve been talking with a lot of
MSP founders about their business goals.

Most talk about revenue targets, growth plans,
and the big milestones they want to hit.

Almost none talk about working on themselves,
especially their health, energy, or ability to focus.

Yet those are the things that shape everything else.

Putting yourself last doesn’t show commitment.
It quietly weakens the business you’re building.

When a founder is burnt out, decisions slow down,
judgment gets cloudy, and leadership turns reactive.

A healthier operator leads with clearer decisions,
more patience, and builds stronger companies.

Business isn’t something you power through once.
It’s something you have to sustain long term.

That’s why my coaching goes beyond systems
and focuses on helping you grow with the company.

Because the same template won’t fit every founder,
and leadership isn’t something you can copy and paste.

If this hits close to home, send me a DM.

Let’s make 2026 your strongest year yet.

Team meetings are one of the most important things
on your calendar if you plan and run them properly.

They’re how you keep your team aligned and moving as
a unit, especially when your business starts to grow.

When things get busier, communication starts to
fragment and conversations become more reactive.

Most of the day ends up in Slack messages,
quick check-ins, and one-off decisions.

What tends to get lost is shared thinking,
which is why a simple meeting cadence is so important.

At a minimum, every business needs 3 core meetings:

A weekly meeting to stay aligned and adjust in real time.
→ What matters this week.
→ What’s stuck.
→ What needs a decision now.

A quarterly meeting to slow things down.
→ Look at what really happened.
→ Reset priorities.
→ Decide where focus should be next.

An annual meeting to think beyond the next quarter.
→ Talk long-term direction.
→ Set meaningful goals.
→ Recap the year and prepare for the next.

These meetings create space for real conversation,
stop the same issues from looping every month,
and save time because decisions stick.

If they aren’t scheduled, they won’t happen.
If they’re inconsistent, they lose their value.

So put them on the calendar, stick to an agenda,
and protect that time like you would a client call.

If you want the agendas I use and recommend,
DM me the word MEETING.

Leadership skills don’t magically show up.
They have to be built with purpose and intention.

If you want employees who can run the business
without you, there’s a simple progression that works:

First, explain the outcomes you care about.
→ Not the tasks or every step.
→ Just what success looks like.

Next, teach them how you think.
→ How you weigh tradeoffs.
→ What you prioritize under pressure.

Then let them run with it.
→ They won’t be perfect, and they’re not supposed to.
→ Growth happens when they can try, miss, and adjust.

The part most owners skip is the last step.

You have to come back and debrief.
→ What worked and what didn’t.
→ What they’d do differently next time.

That’s where learning actually sticks.

It’s how confidence gets built.
It’s how motivation shows up.
It’s how leaders actually emerge.

If people aren’t allowed to fail, they won’t want to try.
So they stay dependent, and you stay stuck.

If you’ve got someone on your team with potential
and want a clear path to help them step up, DM me.

Why speed, autonomy, and accountability all start with trust. As a business grows, decision-making naturally slows down. What used to happen in one co

Open article: Scaling Trust: The Leadership Multiplier Most Founders Ignore by Shawn Freeman • 4 min read

Scaling Trust: The Leadership Multiplier Most Founders Ignore

Reminder: Your value as an MSP goes far beyond
reactive support, security, and tickets alone.

You get a perspective most business owners never see.
A front-row seat to how other companies operate.

Over time, patterns start to show up.

When you see something working well at one client,
you can bring that insight to another.

Not as theory or best practice.
As something you’ve seen work in real life.

This is also why niching your ICP helps so much.

When you work with the same type of business,
you learn their tools, their software, and their workflows.

You start to recognize what usually slows them down
and where small changes make a real difference.

Even without a tight niche, this still applies.

Any time you see a better way to do something, you
can help another client avoid learning it the hard way.

That’s how you move beyond being just IT support.

You become a trusted advisor who helps the business
run more smoothly, more efficiently, and more profitably.

At that point, you’re no longer competing on price.
You’re winning on insight and outcomes.

You’re the one connecting the dots, spotting patterns
and suggesting changes to save time and ease friction.

That kind of value is hard to replace.

Clients don’t switch away from someone
who makes their business easier to run.

They don’t shop for cheaper when they trust you
to help them see what’s coming next.

The best part is, this isn’t something you need to build.
You already have the perspective.

You just have to start using it and translating it
into outcomes your clients care about.

If you want help stepping into that advisory role, DM me.

Founder | LinkedIn Strategist | Helping founders and fractional CXOs create demand on LinkedIn. Click the link in the featured section to learn more👇

I’ve spent most of my career helping companies scale and learning, sometimes the hard way, where systems break.

From 2004 to 2021, I helped build and scale go-to-market and pipeline systems at companies like Salesforce, Zendesk, Duo Security, and Armorblox. The work spanned sales, sales ops, and pipeline strategy, but the throughline was always the same: designing systems that hold up under real-world pressure.

By 2022, I burned out. I stepped away to rethink how growth, systems, and teams should actually work, especially as software became more distributed, more automated, and less forgiving of failure. Over the next few years, I worked closely with founders and operators, helping them see pipeline, GTM, and execution not as motions, but as designed systems.

That shift changed how I see software itself.

Today, I’m at Temporal Technologies, working on a problem that feels foundational: helping developers build applications that remain reliable no matter what goes wrong. Temporal’s durable execution model gives teams a way to write code that survives crashes, retries, outages, and long-running complexity without pushing that burden onto every developer or every team.

What excites me most is the impact. Some of the world’s best engineers and fastest-moving companies are already building mission-critical systems on Temporal. Helping make that path clearer, safer, and more scalable is a rare opportunity.

I write about:

- How pipeline generation is changing in an AI-native world
- Why traditional outbound, inbound, and attribution models break when AI enters the system
- Designing pipeline as an orchestrated system: humans, software, and AI working together
- Signals over volume: how teams generate predictable pipeline without bloated headcount
- What durable execution and reliability mean for revenue systems, not just infrastructure

If you’re a GTM, product, or engineering leader thinking:
“Pipeline feels harder than it should and the old playbooks aren’t working anymore.”

You’re in the right place.

Andrew McGuire

Some opportunities make you stop and say yes immediately.


I’m excited to be joining Temporal Technologies working on Pipeline Strategy. A company tackling one of the hardest problems in modern software: how to build applications that remain reliable no matter what goes wrong.

Temporal gives developers a new foundation for durable execution, and it’s already powering mission-critical systems for some of the world’s best engineers and fastest-moving companies. Getting to work on a problem this fundamental, alongside people this sharp, is a rare opportunity.

I’ll be working closely with Jim Cyb, after our time together at Duo Security and Zendesk, and I’m excited to build with an incredible group of new teammates, including:

Timothy Hughes, Clair Byrd, Michelle Isenberg, Matthew Cruz Jones, Mike Partin / Pace, David Cole and so many more!

Grateful for the opportunity. 
Excited to get to work. 
Let’s build something durable. 🚀

Helping teams move from fragile workflows to durable systems.

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