EdSales Edge Show

By Josh Chernikoff

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Episodes: 114

Description

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:

  • Real strategy for selling into education systems
  • Conversations with education decision-makers who explain how buying actually happens from the inside
  • Stories from founders, CEOs, and operators who’ve built real traction selling into schools—what worked, what didn’t, and what actually moved deals forward
  • Teachings from the EdSales Elevation Experience, the system used to help education founders move from unclear and invisible to trusted and in demand


You’ll learn how to:

  • Define your Perfect Client
  • Pull the right credibility lever
  • Move from being hidden… to trusted… to building a real lead engine

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
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