The Arrogance of Ed Tech Founders

I recently left an EdTech company, and my time there evolved into a version of Stockholm Syndrome. I identified with the company's founders because I believed a shared goal existed. I had a great middle manager who was a true mentor. I loved the product. Those positive aspects blinded me. I ignored the company's true self, so I was caught there when I should have been elsewhere. This was a company run by Silicon Valley lifers, not educators. Their goals were inherently different than mine.

Three men founded the company I was with. As I think about my time with them, all I keep returning to is arrogance. It’s what permeated my time with them and led to the situation they put us all in. That arrogance focused on two of them, while the third was the programming genius behind the platform.  The programming genius is brilliant and incredibly kind. I don’t lump him in the arrogant pool at all, even though he is the one who would be the most justified if he was. Like I said, he is brilliant.
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As I think back, I should have seen this issue right away. In 2018, I began looking for my next step as I had done what I could as an education technology coach. I began looking into the EdTech industry because I had friends who loved life there. I knew I would be great in a community manager or professional development role. I started exploring my options and was recruited by my former company after a chance meeting at a conference. 

The executive who recruited me was tight with the founders, and I thought it would be in a teacher-facing role. As I interviewed, though, I quickly realized it was sales. Sales scared me. I had heard horror stories about folks not meeting target numbers and being let go. I voiced those concerns in my interview but was quickly told we could teach you.  This is the first point where I should have seen that arrogance. 

I was someone who had never been in sales. I needed time, and I did not get it. Almost instantly, I was in meetings where one of the two arrogant leaders would yell intensely at the sales team about their lack of numbers. I got little training from a salesman with a personal style that was incredibly hard to recreate. They even actively kept me away from learning through the other former teacher on staff whose style would closely resemble mine. I was terrified I would get fired, and mind you, this started in OCTOBER. I was not going to be able to fall back on a teaching job until the following August!

Thankfully (at the time, not sure now), the company hired a wonderful man to lead the education side about a month after my hire. By March of the following year, I had a long call with him late at night, questioning whether I could do the sales job. Things had gotten so depressing on my end that I thought the end was near. At the time, I did not realize that the founder's arrogance meant I was not set up for success. I barely had any training. I did not have support. Most importantly, I was not given time. Sales takes time to develop a process, approach, and relationships. What I realized later, as we cycled through salespeople, it was not me. It was them.

The education leader saw something in me and moved me to a more teacher-facing role in April of the following year to avoid my termination. It meant I had just seven months in the sales cycle, and some were just the SLOWEST months. However, they still had me selling part-time, so I closed with 150K in sales before I was pulled out in September. I look back and am proud of that record, considering where the product was and what happened with salespeople after me. I won’t let the founder's arrogance take that pride from me.

Over the years, the entire sales process and team show a clear picture of that underlying arrogance. The answer to every problem was always that we needed more salespeople.  It was never let’s build community, let's build word of mouth, let’s market, or let’s fully take care of our existing customers. It was always that we just needed more bodies. I think it came back to the fact that the cofounder had the arrogance to believe that he would be selling millions of dollars if he were in the role. Do you know where that got us though? In my five years there, we cycled through close to 20 sales professionals, with only 2 of them sticking with us for a year. I started betting over/under on people because I knew they would likely fail.  Yet, as I sit here today, I see that they are still likely to add more even though the company is close to financial ruin.

It also wasn’t just sales. At the start of the 23-24 school year, the company decided they needed more education users, and they decided to go “free.” That free/grant program was one of the most apparent instances of their true arrogance. It started as a way to challenge the free competitor (they are a non-profit) but became so watered down by the founder that it failed miserably. The idea was to give each education user a “grant license,” and they would love it so much that they would purchase the full license the following year.

The program had massive problems. To start, it was only for 30 kids. Most of our teachers were elective teachers with multiple classes, had over 30 students in one class, or needed more budget control to make a purchase. Yet, as we rolled this out, the message was that they would love things so much they would have no choice but to purchase. There was 0 understanding of our actual users. There was 0 understanding of what would make them buy. It was just an arrogance of our product that the product was so great we won’t be denied. I did try initially to voice my concerns, but after I was shut down I knew there was no point.

Guess who got blamed for the failure, though? The edu team. It wasn’t the absolutely nonsensical water-downed program from the founder. It wasn’t the lack of understanding of what users actually wanted. It was a lack of effort in our arrogant cofounder's mind.

And it did not end with that founder. The second founder has always been one to downplay education sales and uplift consumer sales, even though education had always beaten consumer. He thought our product was so good that parents would not have a choice to purchase even at a high price. He operated under the impression that it was the more significant business to scale, so let's focus there and spend money on it. It basically made the edu team second-class citizens in a company where they held up the bottom line. There was never any accommodation that US parents don’t typically spend money on expensive learning software.

They thought so little of our role on the Edu team that they felt they could replace things I was doing with folks who had never been near a classroom. For all of us who have been in education, we know that you have to talk the talk. Teachers will figure out the fakes quickly. I imagine that’s where things will be headed soon. I even offered to stay on part-time just to help with that voice, but that arrogance peaked its ugly head through again.

I repeatedly saw this arrogance shoot us in the foot in so many other instances. It even led us to where we are today, waiting on promised financial benefits that may never come. 

It pains me to write this, but I know this story is not exclusive. There are others in that same boat with other companies. I let what I thought was the needed ruthless businessman mentality excuse many of these behaviors. Ultimately, it shot me in the foot, and I would love to have those 5 years back. Hopefully, others can learn from my mistakes.
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And that’s not to say that founders are all bad. I have met many EdTech founders over the years and had great relationships with several. Even with those folks, though, I can see where the arrogance may have killed them with just a little adversity. Thankfully, I am free of that, and I am led now by a leader here to make things truly better for kids instead of some sort of payout or pumping up his own ego. I am not kissing that ring anymore.