Founder @MSP Consulting | Enterprise Sales for Startups | $2M => $10M ARR

Most founders aren't bad at sales. They're just alternating between winging it and following playbooks that were built for companies 10x their size. I never planned on a career in sales (I studied International Relations). But when I ended up in sales I realized it was the same skill...understand a situation deeply, then tell a persuasive story around it. The further I got in my career the more I kept seeing the same thing. Companies hit the same walls at the same stages and made the same (avoidable) mistakes. And most of the advice for founders was either way too complicated or built for someone else's business. I didn't want to manage bigger teams at bigger companies. I wanted to help founders solve sales problems before they burned 12-18 months figuring it out the hard way. I work with B2B SaaS founders between $1-$10M in revenue who are building enterprise and mid-market sales orgs. I help them cut through the noise, find the highest-leverage fix, and build something repeatable (without overcomplicating it).  No generic advice or playbooks borrowed from $500M companies. Just proven frameworks built for your stage. If you're a founder building enterprise sales or leading a team that needs to get unstuck, I can help. I'm also open to podcasts, speaking, and brand partnerships. I work with brands whose products I use and love and that aligne with my values. Book a strategy session below. You'll leave with clarity on the biggest thing slowing you down right now, and how to fix it. 

Monica Stewart

VP Sales | 🚀 Propelling SaaS Companies to New Growth | Lifelong Sales Mentor and Teacher

Education is locked in outdated models while technology races ahead. So I bridge the gap and build the frameworks that define the future of learning.

I’ve spent my career moving between classrooms, boardrooms, and uncomfortable conversations about what actually works in education.

I started as a teacher.
Then, I moved into EdTech sales—helping founders, school leaders, and teams scale products, revenue, and strategy in one of the hardest markets there is.

Along the way, I noticed a pattern most of us avoid naming:

Education doesn’t fail because of a lack of tools.
It fails when motivation disappears—and we keep building systems that ignore that.

We’ve tried dashboards.
We’ve tried content engines.
We’ve tried accountability without agency.

And we keep acting surprised when students disengage.

My work now sits at the intersection of:
•	Learning science & motivation
•	AI-enabled mastery-based learning
•	Go-to-market strategy for education companies
•	Helping schools raise standards without burning people out

I’m especially interested in models where:
• students love school
• learning is deep, fast, and human
• technology gives time back instead of taking it
• and schools can actually sustain themselves

I advise founders, operators, and education leaders who want outcomes—not applause.

I’m the author of The Great Unlock—a practical, contrarian look at how AI can break education’s three biggest constraints and make learning more human, not less.

No hype.
No grownsplaining.
High standards. High support.

If you believe students are capable of more—and that education should finally be built around that belief—we’ll get along just fine.

Karim Kuperhause

Over 80,000 teacher applications.

Let that sink in.

Alpha School received more applications than most entire school districts see in years. Many big districts would be thrilled with a fraction of that.

This isn’t a fluke.
And it’s not a labor market anomaly.

It’s a signal. 🚨

Because here’s the real takeaway:

The teaching profession isn’t dying.
What’s dying is the traditional teaching model.

Teachers aren’t burned out on:
--> kids
--> learning
--> purpose
--> impact

They’re burned out on:
- being asked to do everything except teach
- rigid pacing guides that ignore mastery
- classrooms optimized for compliance, not learning
- systems that confuse time-on-task with outcomes

When a school redesigns the job:
--> clear outcomes
--> everage (yes, including AI)
--> smaller cognitive load
--> real autonomy
--> respect for professional judgment

Teachers don’t leave.

They line up.

80,000 applications isn’t about Alpha specifically.
It’s about pent-up demand from educators who still love teaching...
...but no longer want to sacrifice their sanity to do it.

The narrative that “no one wants to teach anymore” is lazy.

A better one is this:

Teachers want to teach. They just don’t want to teach in a broken system.

Fix the system, and the talent floodgates open.

Funny how that works.


________________________

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The Great Unlock

Get a preview of my upcoming book at https://thegreatunlock.com/

AI SHOW @ ASU+GSV 2025 Attendee

HierSales is about providing a hierarchy in your sales process. Putting systems in place to consistently grow revenue. We put in place scalable and repeatable sales processes to drive revenue growth for companies in the $1-5M stage.

Most companies are still running outdated GTM playbooks.

Big budgets go into ads, MQLs, and funnels that don’t actually build trust or drive outcomes.

That’s where HierSales comes in.

I help founders and revenue leaders invent their own growth playbook instead of borrowing someone else’s. My methodology is simple but powerful:

Identify → Amplify → Multiply

•	Identify the sparks already driving traction — peer influence, referrals, customer wins.

•	Amplify them through customer champions and authentic founder-led storytelling.

•	Multiply by turning those sparks into repeatable, scalable growth motions (councils, referral loops, influence dinners).

With HierSales, I work hands-on with early-stage and scaling companies to:

•	Run growth ethnography that uncovers where influence really flows.

•	Design influence programs that turn customers into your best sellers.

•	Build 12-week experiment roadmaps to test, validate, and double down on what actually works.

•	Codify it all into a playbook that accelerates growth sustainably.

I don’t just consult from the sidelines. I’ve built, scaled, and sold in the trenches — from teaching in classrooms to leading enterprise sales to scaling EdTech ventures. That practitioner’s lens means I can spot the hidden levers most consultants miss.

If your growth engine feels stuck, or if you’re tired of burning budget on campaigns that don’t convert, let’s talk. Together, we’ll write the playbook that finally unlocks your next stage of growth.

Founder/Fractional VP Sales

“Transform the education of tomorrow, today.”

Provide strategic direction for the Trafalgar-McGill CoLab: https://www.trafalgar.qc.ca/community/colab

Board Member

"I wish you to gasp not only at what you read but at the miracle of its being readable.' - Vladimir Nabokov

The education system is in crisis. Too many students are reaching grade 4 not able to proficiently read at level. This can't go on - children deserve to read and Hoot Reading is on a mission to help every child become a reader.

VP of Growth

“Systems streamline success; they eliminate the need to reinvent the wheel every time.” - J.R. Rim

commonsku is a SaaS platform that enables promotional products distributors to automate and streamline their processes in order to grow and scale their business, including their e-com.

Built entire sales team and sales processes from scratch and went on to Increase client base from 600 to 800 companies propelling transactional revenue from $1B to nearly $2B in 18 months.

VP of Sales

“An organization‘a ability to learn, and translate that learning into action rapidly, is the ultimate competitive advantage.” - Jack Welsh

Clevr helps school districts consolidate and centralize manual forms and workflows into one clevr platform.

Developed and executed go-to-market strategy for landing and expanding into the US K-12 market. Landed in 7 US states and expanded market share which resulted in 45% year-over-year growth as well as landing the biggest client in company's history.

Director of Sales

“Efficiency is doing things right; effectiveness is doing the right things.” - Peter Drucker

Driving efficiency and transformation while reducing the cost of compliance for public sector organizations by providing the Laserfiche Enterprise Content Management platform.

Introduced Laserfiche's digital transformation suite of solutions in new verticals including K12, NGOs and banks. Continued expansion into municipals, hotels and retail. Together, these resulted in a double of revenue year-over-year.

Director, Business Development

“People buy from people they trust”

Help school districts increase student growth by better managing K12 talent through focused talent management software.

Landed and expanded new SaaS solutions into the Canadian K12 market while building out a dedicated sales team and process for Canada.

Account Executive - People Admin

“Systems thinking allows us to see the consequences of our decisions before we make them.”  - Peter Senge

Harnessing the power of research to inform data-driven hiring and increase student achievement. Hit President's Club year-over year as well as becoming the recipient of the Pinnacle Award for highest sales achievement and the Rainmaker award for closing the biggest deals in company history.

Sales Manager - TeacherMatch

“Putting the right people in the right seats is the first step to creating an effective system.” - Jim Collins

Strategically work with school districts from coast to coast to help minimize lost learning days by addressing teacher absenteeism and professional development through the SmartFindExpress software platform. Hit President's Club on my first year and subsequent years thereafter. Landed biggest deal in company history for Canada, locked up the Ontario market and landed and expanded into the Quebec market.

Regional Sales Manager (Canada) - eSchool Solutions

“Building a business is about creating a system that can run and grow without you.” - Robert Kiyosaki

Founder and CEO of the Learning Box which was dedicated to ensuring school success for students in K-12.  Providing individualized instruction based on skill based learning for all core subjects. Went to oversee programs in over 32 schools, 3 learning centres and service thousands of students.

Founder/CEO

“Great leaders understand the importance of developing systems that outlive them.” - John C. Maxwell

As an elementary school teacher for 12 years in this school board, I worked with students from K-6.  I was a lead teacher for school reform and a trained SmartBoard Instructor as well as First Steps Instructor.  My students consistently scored in the top percentile across the entire school board in both math and English language arts.

It's also where I learned many of the skills that made me an exeptional sales professional because teaching and sales are two sides of the same coin.

Elementary Teacher

From ABC to ARR | K12 Education Top Voice | Outcomes. Or. Nothing.

podcasts.apple.com

Future of Education Podcast

I curate the future of learning | Helping EdTech founders and Education Leaders co-design the future of learning

We have 17 versions of an iPhone in 17 years, and we're still using the same version of education we've used for a hundred years.

Think about that for a second.

We upgrade our phones every year because:
• they get faster
• they get smarter
• they adapt to how we use them

But when it comes to kids?

Same time-based system.
Same age-based grades.
Same “move on even if you didn’t get it” logic.

Version 1.0.
Still shipping.

And then we act surprised when students are disengaged, anxious, or bored.

Here’s the uncomfortable part (said gently, I promise):
Education didn’t stagnate because we lack effort or care.
It stagnated because the system was never designed to upgrade.

The factory model worked when:
• information was scarce
• customization was impossible
• scale mattered more than outcomes

None of that is true anymore.

We now live in a world where:
• mastery can be personalized
• feedback can be instant
• pace can adapt to the learner

In every industry except education, that combination would trigger a total redesign.

This isn’t about blaming teachers.
Or dunking on schools.
Or chasing shiny AI objects.

It’s about finally admitting this:

If we wouldn’t accept a 100-year-old phone,
why are we forcing kids to use a 100-year-old learning system?

Education doesn’t need a patch.
It needs a version upgrade.

And the kids are more than ready for v2.0. 🚀

What if school worked like a video game

Kids want to do hard things.

Not busywork things.
Not checked-the-box things.
Hard things — with someone in their corner.

We understand this instinctively in sports.

We sign kids up for hockey, soccer, gymnastics, football, track.
We expect:
• missed shots
• lost games
• bad races
• frustration
• tears

And we’re... fine with it.

Why?

Because we believe something important:
Failure + coaching + repetition = growth.

Now switch to academics.

A bad math test?
Concern.

Struggling to read?
Intervention.

Falling behind?
Lower the bar. Modify the standard. Reduce the expectation.

Same kid.
Same brain.
Totally different rulebook.

Why the double standard?

In sports, we start with high standards and add support.
In school, we often start with comfort and subtract challenge.

But kids don’t rise to comfort.
They rise to standards — when they’re paired with belief and coaching.

The sports playbook works because it’s simple:
• Clear goals
• Immediate feedback
• Permission to fail
• Relentless practice
• A coach who says: “I know you can do this. Let’s try again.”

If we truly want kids to excel academically, we don’t need a new philosophy.

We need the same one we already trust — just applied to learning.

High standards.
Real support.
Try again.

That’s not pressure.
That’s respect.

The moment I realized AI leadership had nothing to do with technology was when a teacher said:

“I’m not scared of learning new tools. I’m scared of not being needed anymore.”

That’s not a technical concern.
That’s a human one.

Leaders who get AI right will be remembered not for moving fast —

but for protecting the people who make learning possible.

The best way to start with AI in schools is by giving time back to students.

Not by automating instruction.
Not by speeding up curriculum.

But by removing the tasks that quietly pull adults away from relationships.

When AI helps with planning, documentation, or communication, something important happens:

teachers get more time to notice
more time to listen
more time to respond

If AI doesn’t create more space for human connection, it’s not helping learning.

The right starting point isn’t efficiency.

It’s presence.

One AI boundary every school system should state clearly:

AI will not replace professional judgment.

Teachers make decisions in context — with students, relationships, and lived experience in mind.

AI can assist.
It can suggest.
It can organize.

But it cannot replace human judgment.

When leaders say this out loud, fear lowers.

Boundaries don’t slow progress.
They make it safe.

There are parts of teaching AI will never replace.

Not because the technology isn’t powerful —
but because the work is human.

Noticing when a student’s behavior changes.
Adjusting in real time when a lesson isn’t landing.
Building trust that makes learning possible.

Any AI strategy that doesn’t explicitly protect these parts of teaching is missing the point.

The goal isn’t smarter systems.
It’s more human classrooms.

I read through 20 district "AI Policy" documents over the holidays.

Most of them are identical. They focus entirely on detection. They assume:

If we block ChatGPT, students will write.
If we use AI detectors, we preserve integrity.

But when I spoke to the teachers in those districts this month, I heard a different story. The detectors are flagging their best writers (false positives). The blocks are pushing kids to use AI on their phones, off the network, where no one can guide them.

We are trying to solve a motivation problem with a firewall solution. Students don't cheat because technology exists. They cheat because they don't see the value in the struggle of writing.

We are spending millions on "AI Guardrails." We should be spending that on "AI Agency." Teaching students why their voice matters more than the algorithm's output.

If your product is designed to catch students, you're fighting a losing war.
If your product is designed to make students want to think, you win.

No login. No rostering. No privacy issues.

If I pitched you a new EdTech platform today, your CTO would immediately ask:
"Does it integrate with Clever?"
"Is it COPPA compliant?"
"Where is the data hosted?"
"How long will the implementation take?"

We have let the "Business of School" strangle the "Business of Learning."

The Myth: Educational software requires complex identity management and strict 1:1 device ratios to function.

The Reality: The OneTab proves you can strip away the entire administrative layer and get better results.

Because the device relies on real-time adaptive assessment rather than stored user profiles, it creates a massive operational unlock:

Zero Setup: You don't spend September uploading CSV files of student rosters. You open the box and hand it to a child.

No Data Liability: It doesn't know the student's name, age, or address. There is nothing to steal. The PII risk is zero.

True Scalability: You don't need a device for every child. You can have a class of 30 share 10 tablets. The software adapts instantly to whoever is holding it.

We are currently paralyzing our schools with "Implementation Fatigue." Teachers spend more time managing logins than managing literacy.

While North American districts are drowning in dashboard management, this solution is delivering high-dosage tutoring without a single password reset ticket.

Sometimes, the most "advanced" technology is the one that knows when to get out of the way.

onebillion.org

one app that delivers reading, writing and numeracy

AI isn’t cheating.
It’s a superpower.

For most of school history, learning has had a hidden bottleneck: waiting.

Waiting for the teacher to get to you.
Waiting days (or weeks) for an assignment to be graded.
Waiting for the next explanation, the next note, the next permission slip to move on.

And if you got stuck?
You stayed stuck. Politely. Quietly. Until help arrived.

AI breaks that model.

With AI:

You don’t wait to get unstuck — you ask.

You don’t wait for feedback — you iterate.

You don’t wait for permission — you proceed.

Go fast.
Go slow.
Go sideways if that’s what understanding requires.

That’s the real shift: agency.

AI gives students control over:

when they practice

how they get feedback

how many reps they need

how deep they want to go

Not by replacing teachers — but by removing friction.

Teachers stop being human traffic lights.
Students stop being passengers.

This is why AI isn’t about automation.
It’s about momentum.

The most powerful learning moment isn’t when someone explains something to you.

It’s the moment you realize:
“I don’t have to wait anymore.”

That’s not just a productivity gain.
That’s a mindset shift.

And once students experience agency...
they don’t want school to go back to waiting.

One simple test for any AI use in schools:

Does this give students more time with a caring adult?

If the answer is no, pause.

The most responsible uses of AI aren’t flashy.

They quietly remove the work that pulls teachers away from:

noticing who’s struggling

responding in the moment

building trust that makes learning possible

When AI gives time back to students, teachers don’t become less important.

They become more present.

That’s the kind of progress worth protecting.

If teachers ever feel replaceable, AI has already failed.

Not because the technology is dangerous —
but because leadership lost its anchor.

Teaching is not a set of outputs.
It’s judgment, care, and trust in real time.

AI should make those things more visible, not less.

Any strategy that forgets this will struggle — no matter how sophisticated it looks on paper.

Language matters more than leaders realize.

❌ “AI will help us be more efficient.”

✅ “AI should give teachers more time to focus on students.”

❌ “This will modernize instruction.”

✅ “This should reduce workload, not increase pressure.”

The words we choose signal intent.

And right now, teachers aren’t listening for innovation —
they’re listening for reassurance.

A teacher once asked me:

“Is AI coming for my job?”

The most effective response wasn’t technical.

It was human:

“No. And if it ever feels like it is, we’re doing something wrong.”

That sentence doesn’t solve everything —
but it signals intent.

And in moments of uncertainty, intent matters more than explanations.

A district leader once told me:

“I’m not afraid of AI. I’m afraid of losing my teachers.”

That sentence captures the real challenge.

This isn’t about keeping up with technology.

It’s about leading change in a way that people can survive — and even believe in.

Much of The Great Unlock came from this exact tension.

The leaders who get AI right won’t be the fastest.

They’ll be the most trusted.

————

https://thegreatunlock.com

When leaders talk about AI, teachers are listening for one thing:

Where are the boundaries?

Try saying this:

“We will not use AI to replace professional judgment.”
“We will not use AI to evaluate teachers.”
“We will use AI only where it increases time with students.”

Boundaries don’t slow innovation.

They make trust possible.

AI isn’t an innovation challenge.
It’s a trust challenge.

Most AI conversations in education fail before they begin — not because the tools are wrong, but because the order is wrong.

We start with technology
when teachers are still asking,
“Where do I fit in this future?”

Until leaders answer that question with clarity and care, no amount of pilots, PD, or platforms will matter.

AI leadership starts with people — not products.

Every time AI shows up in a staff meeting, the same unspoken question hangs in the air:

“Is this thing coming for my job?”

It’s a fair fear.
Education has a long history of “innovations” that promised liberation and delivered... more admin.

But here’s the contrarian truth:

AI isn’t here to replace teachers.
It’s here to finally remove the parts of the job that never should’ve been theirs in the first place.

Grading the same worksheet 120 times.
Chasing compliance instead of curiosity.
Teaching to the middle because the system can’t flex.

That’s not why anyone became a teacher.

AI flips that equation.

When machines handle:
• practice
• feedback
• pacing
• personalization

Teachers get their most valuable asset back: time and attention.

Which is why this line stopped me in my tracks:

“I think the teacher's role is going to move more towards a social worker focusing on social emotional learning,” says Reed Hastings.

That’s not a downgrade.
That’s a promotion.

Because motivation, confidence, belonging, resilience, and trust have always been the bottleneck in learning — we just forced teachers to play data clerk instead.

AI doesn’t make teaching less human.
It finally makes it human-first.

The schools that win won’t use AI to scale content.
They’ll use it to scale care.

And the teachers who thrive won’t compete with machines.
They’ll do what machines can’t:

• build relationships
• coach identity
• unlock belief
• help students want to try again

If you’re a teacher feeling uneasy right now, good news:

You’re not becoming obsolete.
You’re becoming essential.
_____________________

The future of education doesn’t need fewer teachers.
It needs more human ones.

the74million.org

Netflix’s Reed Hastings on the Impact of AI on Schools

Fight AI with AI.

That’s the whole strategy. Everything else is noise.

If you try to outlaw AI in schools, you’re already behind.
If you try to out-detect it, you’re playing whack-a-mole with a supercomputer.

The real move?
Use AI against the problems we’ve tolerated for decades.

Fight AI with AI to:

catch shallow thinking early and force real understanding

close learning gaps in days instead of semesters

personalize pace without lowering standards

give instant feedback that doesn’t depend on teacher heroics

make mastery visible, not performative

This isn’t about letting students “cheat.”

It’s about removing the hiding places.

AI makes it painfully obvious when a student doesn’t understand.
AI makes it impossible to fake fluency.
AI shines a floodlight on systems built for compliance instead of learning.

And that’s why the resistance is so emotional.

Because once AI handles:
practice
feedback
scaffolding
pacing

we can’t blame time, class size, or paperwork anymore.

All that’s left is intent.

What do we expect students to know?
How high are we willing to set the bar?
And will we finally give students the support to clear it?

AI doesn’t weaken education.
It tells the truth about it.

Fight AI with AI.
Or keep fighting the future and calling it rigor.

Intrinsic motivation, good. 
Extrinsic motivation, bad.

This idea has become one of the most unhelpful myths in modern thinking about learning, work, and performance.

We’ve told ourselves a comforting story:
If motivation is “pure” and internal, it’s good.
If it involves rewards, incentives, or external pressure, it’s corrupt.

Reality is messier. And far more human.

Most people don’t start motivated.
They start uncertain.
They start behind.
They start unsure whether the effort will even pay off.

Extrinsic motivation isn’t the enemy.
It’s often the on-ramp.

Deadlines get us started.
Feedback keeps us going.
Recognition signals that the work matters.
Progress markers tell us we’re capable.

And here’s the part we rarely say out loud:

Intrinsic motivation often shows up after competence, not before it.

People don’t love doing things they feel bad at.
They love doing things once they experience progress, mastery, and agency.

The real problem isn’t extrinsic motivation.
It’s lazy extrinsic motivation.

Bribes without meaning.
Rewards disconnected from effort.
Incentives that ignore dignity, autonomy, and growth.

When external motivators are aligned to:
• clear standards
• visible progress
• earned success

They don’t kill motivation — they create it.

We don’t need a purity test for motivation.
We need better design.

Because waiting for intrinsic motivation to magically appear is how people get left behind.

Design for momentum first.
Meaning follows.

If we truly care about outcomes — in schools, teams, or organizations — we have to stop arguing ideology and start engineering motivation that actually works.

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The Battle

Monica Stewart

Karim Kuperhause

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