EdSales Edge Show
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.
EdSales Edge Show
Sher Downing: On Taking Risks, Climbing Ladders and her "Journey" to the Top
Sher Downing has been a successful business owner for over 20 years. She’s become the go-to in the ed-tech space and also hosts her own podcast, “Ed-tech Speaks”. But Sher told us that she never discounts her own humble beginnings as an employee of a music store that really prepared her to climb the ladder in her own career. We were lucky to have Sher join us in this episode as she tells us all about risk-taking, building relationships, and the soundtrack that got her there.
Don’t Stop Believing
At first glance, it might be hard to conceive how experience as a customer service worker at a mom-and-pop music store would have set one up for success as a leader in the ed-tech industry. But Sher told us that it’s a no-brainer. In the 80’s, the music store hosted a variety of diverse customers, as it was the only place to buy or rent instruments and the music to accompany them. From reverends to rock stars, Sher had to know her customer, their needs and their preferences. She learned how doing your homework deepened relationships, and brought paying customers back again and again. This skill set her up for success in her own business, later on down the road.
Anyway You Want It: Distance Education in the 90sSher told us that she had a high school teacher who was great with the kinds of kids who didn’t follow a straight path. He once told her, “You always manage to be driven toward a messy situation and you always make it work. Keep doing that. It will make a difference as you go forward.” It was this advice that stayed with Sher as she entered her career in ed-tech before the internet was a thought, much less what it is today.
Sher told us that EdTech in the 90’s was referred to as, “Distance Education” as it basically consisted of mailing exams through the postal system. Enter, the internet and everything changed. People started talking about how they could use it for educational purposes. “ I was in the right place in the right time,” Sher says, “I grew up with all the big tech available now but they were Betas and Version 1. We were a trial space and helped them learn and grow. We were just at the beginning.” Sher told us that students would go to campus for online classes because they didn’t have access to the internet at home. Seeing how far we’ve come is so exciting to Sher. The more online ed and ed-tech grew, the more she saw it as a problem to be solved. There’s always something to be challenged by which is exactly what she loves about it. Looks like her teacher was right after all.
After All These Years: Consulting Advice
Sher told us that ed-tech was a hard sell at first, considering how traditional education is and cares to remain. She describes how she used the perfect storm of a dangling carrot and a good amount of risk taking to get the ball rolling. Now, she helps others do the same. The core of what she does and encourages others to do is simple, yet effective: focus on relationship building. “Really look at what’s coming,” Sher says, in order to develop connections. This is where her background in research at the music store comes in handy. Sher is continuously reading and researching about the needs of her audience and new developments in the industry. She always has her finger on the ed-tech pulse. “Safe space doesn’t move, risk spaces move,” according to Sher. In order to feel confident in the risk-taking, you have to do your homework.
If you want to hear more about Sher’s background in ed-tech such as her experience as a Beta for the first developed LMS Blackboard, advice on how to navigate strategy and relationship development, and other stories of her journey to the top, listen to the full episode.
