You found the competition.

You looked at the application.

Then you told yourself: "We're not ready."

And maybe you're right.

But what if that's exactly why you should apply?

In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, challenge one of the most common excuses education founders and teacherpreneurs make: waiting until they feel ready before putting their business in the arena.

Because competitions aren't just about winning money, trophies, or a spot on a stage.

They're pressure tests.

Whether it's the Milken-Penn GSE Business Plan Competition, South by Southwest EDU, ASU GSV Cup, StartEd/EdTech Week, or Shark Tank-style competitions, the value isn't limited to what happens if you win. Grants like SBIR and IES create another opportunity to put your business through a rigorous evaluation while pursuing non-dilutive funding.

The application forces you to answer questions you may have been avoiding: Who actually buys this? What problem are you solving? Why does your solution win? What's the evidence? How big is the opportunity? What's different about you? And how do you scale?

If you can't answer those questions clearly, the competition didn't expose your weakness.

It exposed your next move.

WHY THIS MATTERS

Education founders and teacherpreneurs get so close to their businesses that they can't always see what's missing.

A competition or grant application creates productive pressure, feedback, and a chance to challenge your assumptions.

Sometimes the most valuable outcome isn't advancing.

It's finally seeing what needs to change.

KEY STRATEGIES & MENTAL MODELS

1️⃣ Fear is a liar. Avoidance is fear's best friend.
"We're not ready" can be an honest assessment—or an excuse to avoid being tested.

2️⃣ The application is a business-development exercise.
Use it to sharpen your buyer, problem, value proposition, market, evidence, and path to scale.

3️⃣ Not winning isn't failure.
Use the feedback to make the next application—and the business—stronger.

4️⃣ Keep swinging.
Some founders apply once. Others keep improving until they advance, reach the finals, or win.

5️⃣ Choose the right arena.
Find opportunities that offer the right mix of funding, feedback, mentorship, exposure, or connections.

WHO THIS EPISODE IS FOR

• Education founders
• Teacherpreneurs
• EdTech leaders
• Education Founders considering competitions, grants, or accelerators

NEXT STEP

Find one competition or funding opportunity that fits your business.

Don't wait until you're certain you'll win. Apply because the process can make you better.

Then text "90 DAYS" to 771-333-4233.
Get the 90-Day Founder Challenge — a practical framework for your next 90 days.

Teacher-founders: limited 1:1 planning sessions are available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and send this to an education founder who's waiting until they feel ready.

Prepare like you plan to win. Take the swing anyway.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

An education company almost always starts with one person: a founder, a teacher, or a practitioner who saw a problem and decided to solve it.

Then something strange happens.

The very person who built the solution disappears behind logos, fonts, taglines, company pages and carefully polished messaging.

Meanwhile, buyers are asking a much simpler question:

"Who are you, and why should I trust you?"

That's where deals are won or lost.

You don't need a better logo. You need more conversations. You need more trust. You need more sales.

Logos matter. Taglines matter. Brand recognition matters. But those things become more important as the business grows. Early on, people are buying the person behind the business.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, explains why so many education founders overcomplicate personal branding, hide behind company pages, and miss the simple truth: people buy people.

WHY THIS MATTERS

Education founders overthink personal branding all the time. They spend months worrying about logos, messaging, websites, and company pages while ignoring the one thing buyers are actually looking for: a person they can trust.

Early on, people buy people.

Your company can deliver the promise, but the founder is often the reason the conversation starts in the first place.

The goal isn't to become famous. The goal is to become known, trusted, and remembered.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ Use the founder to build trust. Use the company to deliver the promise.

Your business shouldn't depend on you forever, but the market shouldn't have to discover it without you today.

2️⃣ Stop posting like a press release.

Announcements teach people about your company. Stories teach people about you.

3️⃣ Show something real.

People connect with honesty, not perfection.

4️⃣ Visibility isn't a sales system. It's the entrance to one.

Story. Trust. Conversation. Sales process.

Every story needs a next step: a webinar, a newsletter, a clear invitation forward.

5️⃣ Give people something to act on, not just read.

A practical next step makes you useful long before you're ever hired.

🎯 WHO THIS EPISODE IS FOR

• Education founders
• Teacherpreneurs
• EdTech leaders
• Consultants selling into schools
• Anyone building a business that extends beyond the founder

🚀 NEXT STEP

Open your last 10 LinkedIn posts and ignore the likes. Ask yourself this question instead:

"How many show something I know, something I've experienced, something I believe, or something my buyer should do next?"

Then text "90 DAYS" to 771-333-4233.

Get the 90-Day Founder Challenge — a practical framework for your next 90 days.

Teacher-founders: a few 1:1 planning sessions are still open.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and send this episode to an education founder who's hiding behind the company page instead of standing in front of it.

The company may deliver the solution.

But the founder opens the door.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

"We're going to stick with what we have."

Every education founder has heard those words. Usually right after their strongest pitch. Usually after a great conversation. Usually after showing hard proof that the thing works.

And that's exactly what makes it sting.

Most education founders think they lost to another company.

They didn't.

In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, dig into one of the hardest truths in school sales:

You're not competing with a rival product. You're competing with familiarity, routine, a packed calendar, a tight budget, and the plain fact that change feels risky even when it's the right call.

School leaders aren't only asking if your solution is better. They're asking if the disruption of switching is worth it.

That's a completely different question — and most pitches never answer it.

WHY THIS MATTERS

Education founders sell what's possible.

Buyers quietly calculate what it will cost them to get there.

While education founders are painting the upside, school leaders are running the numbers on training, rollout, pushback, and who takes the blame if it flops.

That's why "good enough" keeps beating "better."

Not because leaders don't want something better.

Because standing still still feels like the safer bet.

The founders who get this stop pushing harder.

They start asking sharper questions.

KEY STRATEGIES & MENTAL MODELS

1️⃣ You're not losing to a competitor.

You're losing to how comfortable the current system already feels.

2️⃣ Features get nods. Outcomes get signatures.

School leaders remember what changed, not what the dashboard looks like.

3️⃣ Ask, don't argue.

A sharp question opens more doors than the strongest pitch ever will.

4️⃣ Put a price on standing still.

If staying the same looks free, changing will always look expensive by comparison.

5️⃣ Find whose job gets easier.

Your loudest champion is the person whose daily work your solution actually fixes.

🎯 WHO THIS EPISODE IS FOR

• Education founders
• Teacherpreneurs
• EdTech leaders
• Consultants selling into schools
• Anyone trying to move a system that doesn't want to move

🚀 NEXT STEP

Pull up the last deal that went quiet.

Skip the usual question — "how do I push this forward" — and ask a harder one instead:

"What am I actually asking this buyer to give up?"

Text "90 DAYS" to 771-333-4233.

Get the 90-Day Founder Challenge — a practical framework for your next 90 days.

Teacher-founders: a few 1:1 planning sessions are still open.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and send this to an education founder who's tired of hearing "we'll stick with what we have."

Because the real obstacle was never the competition.

It was always familiarity.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

You built the product. You know the problem. You know your solution works.

So why should you have to be the one selling it?

For many teacherpreneurs and education founders, the answer seems obvious: hire a salesperson, find a reseller, or bring in someone with the right connections to get your solution to schools.

But there's a problem with handing off sales too soon.

You may be trying to delegate something you haven't learned yet.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine explores why founder-led sales isn't about becoming a salesperson forever. It's about learning your market well enough to understand who buys, why they buy, what problems they urgently need solved, and what makes them say yes.

Josh shares how Michael Dell learned to pay attention to who was buying newspaper subscriptions—and discovered patterns that helped him target the right people.

That's the real purpose of founder-led sales: market research, discovery, and pattern recognition. Every conversation reveals what resonates, which objections keep appearing, and what moves buyers forward.

A salesperson can't discover your market for you. You have to learn those things first.

Because if you don't, you aren't really delegating sales.

You're delegating confusion.

WHY THIS MATTERS

Teacherpreneurs and education founders don't need to become lifelong salespeople. But they do need enough firsthand experience to understand their buyers before handing the process to someone else.

When you know your ideal client, their problem, objections, and buying triggers, you can build a repeatable process and eventually scale it.

The goal isn't to sell forever. It's to learn enough to teach someone else.

KEY STRATEGIES 

1️⃣ Founder-Led Sales Is Market Research
Early sales conversations reveal what your market actually cares about.

2️⃣ Learn the Buyer Before Building the Sales Machine
Know your perfect client, their problem, and why your solution matters.

3️⃣ Don't Mistake a Sales Problem for a Positioning Problem
Weak sales may point to targeting, messaging, positioning, or offer problems.

4️⃣ Get Enough Reps to Know What Works
You need enough experience to recognize patterns and build a process.

5️⃣ Earn the Right to Delegate
Before handing off sales, make sure you're giving someone a system—not asking them to figure out your market.

WHO THIS EPISODE IS FOR

Teacherpreneurs and education founders preparing to scale
Founders considering their first sales hire
Education companies exploring sales partnerships

NEXT STEP

Ask yourself:

Am I delegating a proven sales system—or asking someone else to figure out my market?

Text "90 DAYS" to 771-333-4233

Get the 90-Day Founder Challenge—a practical framework for your next 90 days.

Teacher-founders: limited 1:1 planning sessions available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this episode with a teacherpreneur or education founder who's ready to scale—but needs to learn the market first.

You don't have to sell forever. Before you hand off the sale, understand the buyer.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

AI has made it faster than ever to find prospects, research school districts, write personalized emails, create LinkedIn messages, and build follow-up sequences.

Education founders can now do in minutes what used to take hours. Yet many are still hearing the same thing: silence.

The problem isn't AI. It's expecting AI to do the one job it was never meant to do—build relationships.

In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, explore how education companies and teacherpreneurs can use AI to generate more leads without sounding like AI.

Using Lionel Messi's preparation for the World Cup as a powerful analogy, they explain why AI should be your equipment—not the player. 

Learn how to use AI to earn more replies by strengthening research, sharpening your messaging, and keeping trust and human judgment at the center of every sales conversation.

WHY THIS MATTERS

AI has lowered the barrier to creating outreach.

It hasn't lowered the barrier to earning trust.

Buyers are getting better at recognizing outreach that feels automated instead of authentic.

The founders who stand out won't be the ones using the most AI. They'll be the ones using AI to strengthen genuine human relationships.

KEY STRATEGIES & MENTAL MODELS

1️⃣ Let AI Be the Equipment, Not the Player

Use AI to research, organize, analyze, and prepare. Human judgment is still responsible for reading the situation, asking better questions, and building trust.

2️⃣ Solve the Foundation Before the Automation

The best prompt can't fix an unclear offer or an undefined ideal customer. Strong positioning comes before stronger AI workflows.

3️⃣ Personalization Starts With Curiosity

Instead of making assumptions about buyers, use research to ask thoughtful questions that open meaningful conversations.

4️⃣ Automate the Work, Not the Relationship

AI can accelerate follow-ups and proposals, but founders should remain the final voice.

5️⃣ Better Conversations Beat More Outreach

The goal isn't simply to send more emails. It's to create messages that deserve a response because they're relevant, thoughtful, and human.

🎯 WHO THIS EPISODE IS FOR

• Education founders using AI to support sales and marketing
• Teacherpreneurs building stronger outreach strategies
• EdTech sales teams looking to improve response rates
• Founders balancing automation with authentic relationship-building
• Anyone selling into K-12 education

🚀 NEXT STEP

Ask yourself:

Is AI helping you build more relationships... or simply send more messages?

Join Josh's upcoming masterclass and learn how to turn more conversations into paying clients.

Text "90 DAYS" to 771-333-4233

Get the 90-Day Founder Challenge—a practical framework for your next 90 days.

Teacher-founders: limited 1:1 planning sessions available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this episode with a founder who's using AI to save time—but wants to make sure it never replaces trust.

The future of education sales belongs to founders who combine smarter technology with stronger relationships.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

Many teacherpreneurs and education founders work hard to build credibility.

They earn certifications, highlight partnerships, showcase awards, and perfect their product.

Yet sales conversations still stall. Buyers understand what they built, but never connect with why they built it.

Without that connection, trust takes longer to build, sales conversations lose momentum, and revenue becomes harder to generate.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, sits down with Peter Mills, founder of Recess Reset, to explore one of the biggest mindset shifts founders face: moving from hiding behind credentials to leading with authentic connection.

Peter shares why he initially avoided telling his unconventional story—from professional dancer to living in India before founding an education company—and how embracing that story transformed his messaging, strengthened conversations with school leaders, and built deeper trust with buyers.

This isn't about personal branding. It's about building trust that leads to better sales conversations and revenue growth.

WHY THIS MATTERS

Whether you're launching, searching for traction, or scaling, trust drives revenue.

Education buyers don't buy products based on features alone. They buy when they trust the founder and believe in the problem being solved.

Your story helps create that trust.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ Stories Create Trust
Credentials may open the door, but authentic stories help buyers remember—and trust—you.

2️⃣ Make Buyers Care Before You Try to Impress Them
The strongest messaging helps school leaders see why the problem matters before highlighting achievements.

3️⃣ Connect Your Story to Your Customer's Reality
The best founder stories aren't biographies. They directly explain the problem your solution was built to solve.

4️⃣ Build Familiarity, Not Just Differentiation
Connecting your solution to tools educators already know makes new ideas easier to understand and adopt.

5️⃣ Lead Every Conversation with Purpose
A simple story, a relatable example, and a clear plan create stronger sales conversations than a product pitch alone.

🎯 WHO THIS EPISODE IS FOR

• Teacherpreneurs preparing to launch an education business
• Education founders struggling to gain traction
• Founders refining their messaging and positioning
• Education companies building trust with school leaders

🚀 NEXT STEP

Ask yourself:

Are buyers remembering my credentials—or remembering why I care?

Text "90 DAYS" to 771-333-4233

Get the 90-Day Founder Challenge—a practical framework for your next 90 days.

Teacher-founders: limited 1:1 planning sessions available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this episode with a founder who's been hiding behind their résumé instead of sharing the story that makes their business matter.

The strongest education businesses grow when buyers trust the founder before they trust the product.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

Every teacherpreneur and education founder starts with the same belief.

If I create something that genuinely helps students, schools will want it.

It sounds reasonable.

But education businesses don't grow on value alone.

They grow when buyers trust the founder, partners strengthen credibility, and the right people help create momentum around the solution.

That's the real conversation in this episode.

Originally recorded live at IFE in Monterrey, Mexico in April 2025, Josh Chernikoff, founder of the EdSales Revenue Machine, sits down with Beatriz Guillen, Executive Director of The Resource Foundation. While the conversation explores philanthropy and education across Latin America, the lessons reach far beyond one region.

Together, they explore a question every education founder eventually faces:

What helps great education businesses become businesses that actually grow?

The answer isn't another feature.

It isn't better marketing.

It's learning to think beyond the solution itself.

From partnerships and buyer confidence to credibility and long-term ecosystem building, this conversation challenges founders to stop asking, "How do I sell this?" and start asking, "What needs to exist before buyers are ready to say yes?”

Why This Matters

Whether you're preparing to launch or already selling into schools, education buyers rarely make decisions on value alone.

They look for evidence.

They look for credibility.

They look for trusted partners.

Founders who understand that build momentum faster, create stronger relationships, and give great solutions a better chance to succeed.

🔑 Key Strategies & Mental Models

1️⃣ Build an Ecosystem, Not Just a Business
The strongest education companies don't grow alone. They intentionally build relationships that create momentum.

2️⃣ Credibility Comes Before Adoption
Evidence reduces risk. Buyers need confidence before they make commitments.

3️⃣ Partnerships Beat Isolation
Strategic partners often create opportunities that marketing alone never will.

4️⃣ Solve for the Buyer, Not Just the User
Great products help students. Great businesses also make buying decisions easier.

🎯 Who This Episode Is For

• Teacherpreneurs building their first education business
• Founders selling into schools or districts
• Education companies seeking strategic partnerships
• Operators navigating long education sales cycles

🚀 Next Step

Ask yourself: Who needs to believe in my business before my next customer says yes?

Text "90 DAYS" to 771-333-4233

Get the 90-Day Founder Challenge—a practical framework for your next 90 days.

Teacher-founders: limited 1:1 planning sessions available.

🔁 Subscribe & Share

If this episode changed how you think about growing an education business, subscribe and share it with another founder.

The strongest education businesses are built through relationships, not just great products.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

Teacherpreneurs often believe growth will follow once they create something that works.

It won't.

A strong solution is the starting line, not the finish line. The hard part is figuring out who needs it, how to talk about it, and how to create demand around it.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine (previously EdSales Elevation Experience) sits down with Grace Pokela, founder of The Lesson Laboratory. Grace built a digital curriculum and instructional model that helped students become active investigators rather than passive learners. The results were real. But like many teacherpreneurs and education founders, she discovered that expertise alone doesn't create a business.

The conversation explores the shift from educator to entrepreneur. From identifying the right buyer to building confidence, developing a signature solution, and learning founder-led sales, Grace shares what it takes to build a foundation before chasing scale.

This isn't a conversation about curriculum. It's a conversation about what happens when an educator decides to build a business.

WHY THIS MATTERS

Many teacherpreneurs spend years mastering instruction and very little time learning positioning, sales, and customer discovery.

The result is often frustration. Strong solutions struggle because the founder assumes results will create demand.

They don't.

Growth gets easier when buyers understand exactly who you help, what problem you solve, and why it matters.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ A Breakthrough Is Not a Business

A solution can be effective and still struggle in the market. Growth begins when founders learn how to position and sell that solution.

2️⃣ Clarity Creates Traction

The clearer you are about the problem you solve and who you solve it for, the easier it becomes to generate opportunities.

3️⃣ Find the Buyer Closest to the Pain

The person with the budget is not always the person who feels the problem most deeply. Understanding that difference changes your sales strategy.

4️⃣ Confidence Is Built Through Action

Founder confidence doesn't come from motivation. It comes from customer conversations, market feedback, and repeated execution.

5️⃣ Build the Foundation Before You Scale

Positioning, messaging, credibility, and pipeline development are not growth accelerators. They are growth prerequisites.

🎯 WHO THIS EPISODE IS FOR

Teacherpreneurs turning expertise into a business

Education founders seeking product-market fit

Educators building their first revenue engine

Teams struggling to define their ideal customer

Founders looking to improve positioning

🚀 NEXT STEP

Ask yourself:

Have I built a business, or have I only built a solution?

Text "90 DAYS" to 771-333-4233

Get the 90-Day Founder Challenge—a practical framework for your next 90 days.

Teacher-founders: limited 1:1 planning sessions available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this with a teacherpreneur who's trying to scale before building a foundation. 

Growth gets expensive when clarity is missing.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

The school year may be ending, but the work of building a business doesn't stop.

For teacherpreneurs, summer creates something rare: space. Space to think, plan, and improve the business while the pace of the school year slows down.

But the lesson extends beyond teacherpreneurs. Every education business owner faces the same challenge: using quieter seasons to strengthen the business instead of simply reacting to it.

In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, discuss why summer is one of the most important seasons for teacherpreneurs. Not because schools are buying more, but because founders finally have space to think, plan, refine, and prepare for what's next.

The conversation explores common mistakes: forcing offers that no longer match buyer behavior, disappearing completely, or staying trapped in delivery work without improving the business itself.

Josh and John share a practical framework for using summer intentionally. From clarifying offers and understanding buyer priorities to creating a focused 90-day plan, this conversation is about building a stronger fall before it arrives.

WHY THIS MATTERS

Growth problems don’t start when sales slow down.
They start when founders stop checking what’s actually working.

Most education businesses enter a new school year carrying the same problems: unclear messaging, weak positioning, inconsistent outreach, and broken sales flow.

Summer is the window to fix it—before those issues get expensive.

The founders who grow aren’t always the busiest.

They’re the ones who use quiet seasons to sharpen their message, deepen relationships, and prepare for the next buying cycle.

KEY STRATEGIES & MENTAL MODELS

1️⃣ Sell Where Demand Is Real

Focus on buyers already showing interest instead of forcing conversations that aren't moving.

2️⃣ Clarify the Transformation

Be able to explain who you help, how you help, and what outcome you create. If buyers can't repeat it back, your message isn't clear enough.

3️⃣ Build a 90-Day Plan

Skip the giant annual strategy document. Focus on the next ninety days. Clear priorities create momentum.

4️⃣ Work on the Business

Use summer to refine your offer, strengthen outreach, revisit goals, and prepare for the next selling season.

5️⃣ Understand What Buyers Care About

Strong founders focus on the problems buyers are actively trying to solve. Summer is a great time to do that research.

WHO THIS EPISODE IS FOR

• Teacherpreneurs building education businesses
• Educators turning classroom expertise into a business
• Founders struggling with sales consistency
• Operators building repeatable growth systems

🚀 NEXT STEP

Ask yourself:

If the fall started tomorrow, would your business be ready?

The next season is built before it arrives.

Text "90 DAYS" to 771-333-4233

Get the 90-Day Founder Challenge—a practical framework for your next 90 days.

Teacher-founders: limited 1:1 planning sessions available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this with a founder who plans to "figure it out" in September.

The next school year gets built long before the first day of school.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

The fastest way to lose trust is to try to earn it too quickly.

That's a difficult reality for education companies.

Dr. Jared Bloom sees it every day.

As Superintendent of Franklin Square School District in New York, Jared receives hundreds of emails every day from companies trying to get his attention. Most never get a response.

Not because the products are bad.

Because that's not how trust gets built.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine sits down with Jared for an unusually honest conversation about what actually gets a superintendent's attention—and why most education sales outreach misses the mark.

Jared explains why cold emails rarely stand out, why generic LinkedIn pitches feel transactional, and what separates a vendor from a true partner.

He also shares how districts evaluate new solutions and why some companies earn long-term trust while others never make it past the first conversation.

For founders, sales teams, and customer success leaders, this episode offers a rare opportunity to hear directly from the other side of the table.

WHY THIS MATTERS

Most education companies assume they have an outreach problem.

In reality, many have a trust problem.

When relationships are weak:

• Every sales conversation feels harder
• Follow-up becomes chasing
• Pilots stall
• Adoption slows

When trust exists:

• Conversations happen faster
• Feedback becomes honest
• Internal champions emerge
• Partnerships last longer

The strongest education sales strategies aren't built around volume.

They're built around credibility.

KEY STRATEGIES & MENTAL MODELS

1️⃣ Relationships Scale Better Than Outreach

The goal isn't more conversations.

The goal is stronger conversations with the right people.

2️⃣ Relationships Are Built In Real Conversations

Face-to-face interactions allow education leaders to understand who they're working with—not just what they're buying.

3️⃣ Start Small, Then Expand

Successful districts start with small pilots, gather evidence, and expand only after results are visible.

4️⃣ Teacher Buy-In Matters

Even the strongest product can fail if the people using it don't believe in it.

5️⃣ Partnership Continues After The Sale

The most successful companies stay involved, listen closely, and adapt based on district feedback.

WHO THIS EPISODE IS FOR

• Education founders struggling to break into districts
• EdTech sales teams relying heavily on cold outreach
• Customer success leaders focused on retention and adoption
• Companies looking to build long-term district partnerships
• Anyone selling into K-12 education

🚀 NEXT STEP

Ask yourself:

Are you spending more time increasing outreach...

or increasing trust?

Because schools rarely buy from strangers.

They buy from partners.

Text "RELATIONSHIP" to 771-333-4233.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this with someone who thinks more outreach is the answer.

Sometimes the real answer is building better relationships.

Connect with Josh Chernikoff

Founder, Edsales Elevation Experience
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

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