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EdSales Edge is the strategy podcast for education founders, consultants, operators, and leaders selling into education.
For years, this show was known as Breaking the Grade, a space to challenge the status quo in education and think differently about how change actually happens. That mission hasn’t changed.
But the work has.
Over time, one thing became clear:
Education founders don’t just need inspiration.
They need clarity.
They need real strategies for selling into schools.
They need predictable ways to generate leads.
And they need to understand how trust is built in a system that doesn’t move fast, and doesn’t give many second chances.
EdSales Edge was rebuilt to match that reality.
Hosted by Josh Chernikoff, a two-time education founder who’s built and exited companies in this space, the show breaks down how selling into education actually works—across B2C, B2B, B2B2C, and B2E—always through the lens of how education institutions really make decisions.
This is not a show about hacks, shortcuts, or quick wins.
Education doesn’t work that way.
On EdSales Edge, you’ll hear:
You’ll learn how to:
Josh is joined by his good friend and mentor, John Gamba—Director of Innovative Programs and Entrepreneur-in-Residence at Penn GSE, and a former education founder who’s led companies through real growth and successful exits. John brings the institutional lens, shaped by years inside districts, universities, and education systems, seeing how decisions get made when the doors are closed and what earns trust over time.
Together, they sit on both sides of the table, the builder side and the system side, so the show stays grounded in reality, not sales theory.
If you sell into education and you’re tired of guessing,
guessing who to talk to,
guessing how decisions get made,
guessing why interest doesn’t convert—
this show is built for you.
EdSales Edge
Clarity. Credibility. Real traction.
If you sell into education, this is where you earn your edge.
| Episode | Date |
|---|---|
|
The Clarity That Came After the Pause: A Triple Bypass, a Forced Stop, and a Fresh Start for My Business.
|
May 31, 2026 |
|
Getting on First Base: An Education Founder’s Guide to Sustainable Growth
|
May 24, 2026 |
|
What I Wish More Education Founders Knew About Their Leads
|
May 17, 2026 |
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Targeting That Scales: How the Right Audience Changes Everything
|
May 10, 2026 |
|
Stop Funding the “Maybe” Trap: You’re Losing $50K in Contracts to Wrong Leads
|
May 03, 2026 |
|
When More Kills Deals: Why Simpler Offers Win in Education Sales
|
Apr 26, 2026 |
|
From Stuck Deals to Simple Wins: How to make education buyers say yes
|
Apr 19, 2026 |
|
From Confusion to Clarity (The Offer That Makes People Say “I Need That”)
|
Apr 12, 2026 |
|
Why Deals Stall (And How To Keep Them Moving)
|
Apr 05, 2026 |
|
Stop Guessing, Start Thriving: Unlocking Clarity in Education Sales
|
Mar 29, 2026 |
|
Listen More, Sell More: From $25K Pilots to $100K Partnerships
|
Mar 22, 2026 |
|
Miss the Signals, Lose the Deal: What Happens When You Don’t Ask and Align
|
Mar 15, 2026 |
|
Listen First. Win Later: How Listening Saves Pilots From Failing
|
Mar 08, 2026 |
|
Listening Beats Pitching in Education (Why Trust Markets Don’t Respond to Noise)
|
Mar 01, 2026 |
|
How Education Buyers Evaluate Credibility (Why Credentials Alone Don’t Build Trust)
|
Feb 22, 2026 |
|
Why Most LinkedIn Advice Fails Education Founders (And What Actually Works)
|
Feb 15, 2026 |
|
Building Trust with Education Buyers: Why Silence Isn’t Rejection
|
Feb 08, 2026 |
|
Why Chasing “Likes” Keeps You Stuck (How Education Buyers Actually Decide)
|
Feb 01, 2026 |
|
Why Selling Software Keeps You Stuck, and Selling Peace Moves Deals
|
Jan 25, 2026 |
|
Why “What You Do” Isn’t Why Education Leaders Buy
|
Jan 18, 2026 |
|
Why the Fastest “Yes” Beats the Biggest Budget — with Dr. Brooke Olsen-Farrell
|
Jan 11, 2026 |
|
The Perfect Client Paradox: Why Chasing More Leads Isn’t the Answer
|
Jan 04, 2026 |
|
Breaking Up with Breaking the Grade (and Why It Was Time)
|
Jan 02, 2026 |
|
Best of 2025: How Education Founders Can Turn Any Conference or Summit Into a Sales Engine That Builds Trust, Authority, and Pipeline
|
Dec 28, 2025 |
|
Best of 2025: Karim Kuperhause & Rose Hastreiter on Why Education Founders Must Sell First, Master Objections, and Build a Repeatable Process Before Delegating or Scaling
|
Dec 21, 2025 |
|
Best of 2025: Robert Martellacci on How Education Founders Stuck Chasing Sales Can Turn Relationships, Setbacks, and Partnerships Into Scalable Credibility and Revenue Growth
|
Dec 14, 2025 |
|
Best of 2025: Jolene Levine on How Education Founders Can Turn Betrayal, Burnout, and Chaos Into a Blueprint for Credibility, Alignment, and Lead Flow That Converts
|
Dec 07, 2025 |
|
Best of 2025: John Gamba on How Education Founders Can Rebuild Trust, Visibility, and Pipeline Through Authentic LinkedIn Strategy
|
Nov 30, 2025 |
|
The Gratitude Episode: 22 Guests, 63 Countries, and a Community That Turned 2025 Into Our Most Meaningful Year Yet
|
Nov 23, 2025 |
|
The Headline Mistake: How eight words on LinkedIn unlocked a $100k repeatable pipeline.
|
Nov 16, 2025 |
|
Hesitation Is a $250K Mistake: Dr. Tamara Minott on How Education Founders Close Deals With Confidence
|
Nov 09, 2025 |
|
You Crushed the Demo—But Still Can’t Close: The $100K Mistake Education Founders Keep Making
|
Nov 02, 2025 |
|
From Betrayal and Courtroom Battles to Closed Deals: Robespierre Reyes on Rebuilding Credibility, Team Alignment, and Education Deals That Close
|
Oct 26, 2025 |
|
From Confusion to Clarity: JD Mosley-Matchett on the Message Shift That Turns Unclear Offers into Scalable, Trust-Building Growth for Education Founders
|
Oct 19, 2025 |
|
The Mindset Reset: Mitch Weisburgh On How Education Founders Can Master Mindset, Beat Burnout, and Close Strong Deals
|
Oct 12, 2025 |
|
Stop Delegating Sales: Why Education Founders Must Sell Their Solution First Or Watch Their Pipeline Die
|
Oct 05, 2025 |
|
From Lost Leads to Locked Contracts: Paul King on Niche Focus, Pilots That Convert, and Closing Education Deals
|
Sep 28, 2025 |
|
The Education Founder’s Blueprint: Kevin Chavous on Turning Setbacks Into Proof Points, Credibility, and Growth That Lasts
|
Sep 21, 2025 |
|
The Guarantee Shift: Karim Kuperhause on How Education Founders Build Trust and Win Qualified Leads Without Sounding Desperate
|
Sep 14, 2025 |
|
From Invisible to Irresistible: Michael Campbell on Using Research and Proof to Build Trust, Generate Leads, and Drive Education Growth
|
Sep 07, 2025 |
|
$9M Raised, Zero Guesswork: How YourWay Raised $9M by Solving the Lead Gen Problem Most Education Founders Ignore
|
Aug 31, 2025 |
|
From “Great Pitch” to Signed Contract: Paul Vallas on the Buyer’s Lens That Closes Education Deals
|
Aug 24, 2025 |
|
(Re-Air) The Signature Solution: Your Proven Blueprint to a Clear Offer That Generates Leads and Wins the Education Market
|
Aug 17, 2025 |
|
From $10M in Sales to Losing Her Company: What Education Founders Learn the Hard Way About Selling, Scaling, and Staying Aligned
|
Aug 10, 2025 |
|
(Best of) Your Demo Is the Problem: What Education Founders Must Do—and Stop Doing—to Close More Deals With Their Demos
|
Aug 03, 2025 |
|
From Collapse to Credibility: Robert Martellacci’s Blueprint to Win Back Influence and Close Deals in the Education Space
|
Jul 27, 2025 |
|
From Dead-End to C-Suite: An Edtech’s Messaging Framework That Converts Education Conversations into Contracts
|
Jul 20, 2025 |
|
Your Summer Fix: How Education Founders Can Rebuild Lead Flow Before Back-to-School
|
Jul 13, 2025 |
|
From Quiet Posts to Real Revenue: How Anissa Used LinkedIn to Build Trust and Attract Qualified Leads
|
Jul 06, 2025 |
|
The Rest Advantage: How Education Founders Use Strategic Pauses to Spark Lead Gen Breakthroughs
|
Jun 29, 2025 |
|
Clearer Messaging, Consistent Leads: What EdTech Founders Can Learn from MindShifting
|
Jun 22, 2025 |
|
Do the Opposite of Everything You’ve Been Doing: How Seinfeld’s George Costanza Unlocks Lead Gen Clarity for EdTech Founders
|
Jun 15, 2025 |
|
Breaking Borders: How Smart EdTech Founders Build Scalable Companies Without Losing Local Trust
|
Jun 08, 2025 |
|
The Speaking Strategy: How Education Founders Fast-Track Credibility, Confidence, and Sales Momentum
|
Jun 01, 2025 |
|
From Ghosted to Booked: How Ashton Tate Filled His Calendar with Qualified School Leads
|
May 25, 2025 |
|
You Don’t Just Sell to Schools—You Earn Their Trust: How Edtech Founder Paul Moch Built an Education Business That Got Acquired
|
May 04, 2025 |
|
Busy Isn’t Booked: The Silent Sales Mistake Most Founders Miss
|
Apr 25, 2025 |
|
Cracking the Code: How to Sell Education Products in High-Stakes Markets
|
Apr 18, 2025 |
|
From Chaos to Clarity: How One Founder Rebuilt His EdTech Biz from the Ground Up to Revenue Way Up
|
Apr 11, 2025 |
|
Why Most Education Companies Burn Out Before They Scale—And the Fix That Actually Works
|
Apr 04, 2025 |
|
LinkedIn Connection to Contract: Josh's Proven Six-Step EdSales Method (No Paid Ads/Funnels/Cold Calls)
|
Mar 28, 2025 |
|
Struggling to Sell to Schools or Universities? (An Expert in HigherEd Tells You How to do it Right)
|
Mar 21, 2025 |
|
The Conference Playbook: How Education Companies Get Conferences Wrong (And How to Fix It)
|
Mar 14, 2025 |
|
IFE Conference 2025 (Mexico): Breaking Barriers -- AI and Strategic Partnerships Shaping Education
|
Mar 07, 2025 |
|
Why Most Startups Get Investment Wrong—and How to Fix It
|
Feb 21, 2025 |
|
Before You Hire a Sales Team...The Steps Founders Can’t Skip
|
Jan 24, 2025 |
|
Secrets behind unlocking 7-figures in sales...How this seasoned entrepreneur transformed his sales process.
|
Jan 10, 2025 |
|
From One-Off Sales to Repeatable Revenue...How Future Makers Transformed Their Business
|
Dec 27, 2024 |
|
Mastering Sales Planning in the Education Space
|
Dec 09, 2024 |
|
Mastering the Education Sales Cycle & Secrets to Staying Top of Mind and Closing Deals
|
Nov 22, 2024 |
|
Why Waiting to Sell in the Education Sector Can Cost You...& when’s the right time to start selling
|
Nov 08, 2024 |
|
A Better Approach to Sales Calls for Education Companies… How to sell without being salesy.
|
Oct 25, 2024 |
|
The Better Demo Method To Sell More Education Services & Products
|
Oct 11, 2024 |
|
How This EdTech Company Transformed Their Sales Process And Went From Stagnation to Leads In Just 8 Weeks
|
Sep 27, 2024 |
|
How this EdTech Startup sharpened their message & went from struggling to selling!
|
Aug 30, 2024 |
|
How this EdTech founder got clarity on his ideal client & product... making selling easier!
|
Aug 16, 2024 |
|
3 Powerful Systems To Grow Your Education Business With More Ease
|
Aug 02, 2024 |
|
3 Essentials To Grow Your Business: Lessons I Learned From Starting, Scaling, and Selling Flex Academies
|
Jul 19, 2024 |
|
Kathryn’s Lead Generation Transformation with the EdSales Elevation Experience
|
Jul 05, 2024 |
|
How to Build A Lead Generation System in 9 Steps
|
Jun 21, 2024 |
|
Rose’s Lead Generation Transformation with the EdSales Elevation Experience
|
May 24, 2024 |
|
Slow Burn Methods for Lead Generation in EdTech
|
May 10, 2024 |
|
How to sell to multiple stakeholders in the education space
|
Apr 29, 2024 |
|
Case Study with David Dvorkin
|
Apr 12, 2024 |
|
Transforming your LinkedIn profile into a sales page
|
Mar 29, 2024 |
|
The most powerful tool to connect with your ideal clients
|
Mar 15, 2024 |
|
Why you need a signature solution to generate more leads and close more sales!
|
Mar 04, 2024 |
|
How to promote your services and products in the education space without feeling icky or salesy
|
Feb 16, 2024 |
|
Growing MyOwl: LinkedIn Strategies for EdTech Startup Growth
|
Jan 26, 2024 |
|
How do you use LinkedIn to get leads for education business?
|
Jan 19, 2024 |
|
Breaking Free from Traditional Goal Setting Methods with Rose Hastreiter
|
Jan 12, 2024 |
|
Sher Downing: On Taking Risks, Climbing Ladders and her "Journey" to the Top
|
Dec 05, 2023 |
|
Erin Dowd: Learning to Love Stories | Sowing Seeds Early in Life
|
Jun 20, 2023 |
|
Susan Gold: On Creativity, Critical Thinking and Being a Kid Whisperer
|
May 02, 2023 |
|
Sher Downing: On Taking Risks, Climbing Ladders and her "Journey" to the Top
|
Mar 21, 2023 |
|
Keltse Bilbao: On Embracing Change and Staying Curious
|
Feb 21, 2023 |
|
Eric Nelson: Who You Become is Just as Important as What You Achieve
|
Jan 25, 2023 |
|
Alberto Rossi: Believing IS Seeing
|
Jan 10, 2023 |
|
Lisa Friedlander: The Bumps and the Bruises That Lead To Brilliance
|
Dec 28, 2022 |
|
Oliver Knott on Providing Hope for Diverse Learners
|
Dec 06, 2022 |
|
Brian Zapf: On Loving Numbers, People and Telling A Financial Story That Soars
|
Nov 01, 2022 |
|
Mike Lawrence: On Putting Students First, an Innovation Index and Ted Lasso
|
Oct 18, 2022 |
|
Breaking the Barriers of Language Learning with Malcolm Lee
|
Oct 11, 2022 |
|
Breaking and Changing the way we Write and Consume Media with Daniel Stedman
|
Aug 26, 2022 |
|
Breaking The Stigma Against Autism with Dr. Celest Austin
|
Aug 05, 2022 |
|
The New Era of Leadership | Breaking The Grade with Dr. Quintin Shepherd
|
Jul 11, 2022 |
|
Bridging the Gap Between Students and Employers with Nancy Soni
|
Jun 17, 2022 |
|
Big Breaks - Celest Austin, GoManda
|
May 26, 2022 |
|
Breaking the Silence: Inequity in Education with Alexa Escobedo
|
Apr 03, 2022 |
|
Let’s Make SEL More Effective with Nicole Lipkin
|
Apr 02, 2022 |
|
Breaking and Rebuilding American Education with Kevin Chavous
|
Apr 01, 2022 |
|
The Importance of Co-creating Products with Your Researchers and What to Expect in the next Episodes with John Gamba
|
Mar 28, 2022 |
|
Breaking the Grade Trailer
|
Mar 08, 2022 |
|
What is Breaking the Grade?
|
Jan 31, 2022 |