After nearly two decades in edtech sales, I learned that success isn’t about louder messaging or better automation—it’s about earning the next conversation through creativity, humanity, and genuine connection.
GUEST COLUMN | by Jason Fennell
“I hope this works out.”
“There is no guarantee this is going to work.”
When I had both thoughts, I was all in regardless.
That first prayer came in July 2006 after I finished my fifth year of teaching, a former student ran a red light totaling our paid-for Honda Accord, and we learned daughter number three was on the way. That prayer preceded me jumping from the deep end into edtech sales.
We’ve worked for edtech companies that were not on any state-approved vendor lists, in the supplemental space, and often seen as a nice-to-have versus mandated. We’ve danced through acquisitions, high school credit recovery, math and reading interventions, science textbook adoption, and now MTSS. Edtech continues to be a rewarding journey because we get to serve education while supporting districts and improving student outcomes.
When the Old Playbook Stops Working
The second epiphany landed in the summer of 2023.
It had been two rough sales years. ESSER funding was drying up. Texas and the TEA continued building state-approved vendor lists. Districts increasingly viewed our supplemental math tools as nice-to-haves.
‘It had been two rough sales years. ESSER funding was drying up. Texas and the TEA continued building state-approved vendor lists. Districts increasingly viewed our supplemental math tools as nice-to-haves.’
As my family has lived off my income since the days of a teacher’s state-based minimum salary schedule, something had to give. Something had to change.
I was looking in the mirror at the only person I knew I could change.
I was desperate for change.
My belief was that my approach was falling flat, simply joining the noise everyone else was creating. Every email, every call, every voicemail competes with every other email and call. In sales, messaging and delivery matter. The endless automation and sequencing habits had become nauseating.
Worst of all, I wasn’t having fun.
Betting on a Different Approach
We couldn’t afford a third tough year.
So I went to my bride, who has always been my live-in regional manager. She could sense it, too. Something had to change.
My answer was to invest in sales coaching through Dale Dupree’s The Sales Rebellion.
Since then, different has never looked or felt so good.
I adopted a personal mantra: As an educator, I needed to engage the people I’m looking to help and serve by earning the next conversation.
That’s where The Sales Rebellion began helping me build my creative muscles.
The nerd in me didn’t think I was creative. What I learned was that I simply hadn’t tried to be creative.
Sales is full of rejection. Mindset matters.
Bringing Humanity Back to Sales
Since that coaching experience, my sales outreach and LinkedIn posts have originated from a new philosophy: show up differently.
Bring humanity back into sales.
Be proud to be in sales.
What does my typical day look like in edtech sales?
It looks like leveraging everyday items to engage and connect. It looks like going to the USPS and shipping boxes across my territory. It looks like delivering items in person and sharing laughs with receptionists.
It’s leveraging popular memes and GIFs while occasionally starring in my own. It’s finding ways to inject fun into the process.
A typical day also means recognizing that success isn’t measured solely by whether an email gets opened or a voicemail gets heard.
Earning the Next Conversation
Success is an email reply.
It’s a message being forwarded to the high school entrepreneurship teacher.
It’s a shoutout on LinkedIn.
It’s a call back.
More than anything, creative outreach is disruptive. It plants seeds for future opportunities. It is playing the long game in a world that constantly pressures us to perform like a microwave.
A typical day in edtech sales can be as fun and genuine as you’re willing to make it.
It’s recognizing the human on the receiving end and treating them like a human.
Do or do not. There is no try.
Earn the next conversation.
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Jason Fennell serves Texas educators as an account executive at Branching Minds and has spent nearly 20 years helping schools implement solutions that improve student outcomes. Connect with Jason on LinkedIn.
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