 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. 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. 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.
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 I was a teacher for ten years, and ten years ago, I faced a choice.
I needed a path to advancement, a path to advancing my family's fortunes, and a path to further my career. At that time, I had become enamored with the EdTech world. It was such a fun place to be in 2014. It was a world filled with fun startups making a difference in classrooms. Most were free because they were just worried about user growth. There were fun speakers, conferences, and things to do. I dreamed about what that world could be for me and jumped headfirst into it. I started in 2014 as a tech coach with Kennesaw State University. This role kept me in schools (we were contracted out), but it also let me spread my wings in the EdTech world. I worked with schools on personalized learning initiatives and spoke at conferences. I built a decent brand and helped create a MakerBus. By the time I got to 2018, I felt like I had done everything I could do there. That choice came back. I faced either returning to schools in some capacity or joining the EdTech vendor side. In 2018, an opportunity came up on the vendor side, and I took it. I spent five years with this vendor, supporting teachers with my hands in almost everything that impacted our education users. I had a great mentor, and I loved having the ability to help teachers from around the world. When 2021 hit, this vendor went through what every vendor wants. They got acquired, and that acquisition has been an unmitigated disaster. Someday, I will tell that whole story, but I need to wait for many reasons. That bad acquisition meant that choice came back again. Do I stay in the EdTech industry or head back to school? My first thought was always the EdTech industry, but getting the proper role in the industry proved challenging, and it started with my previous experience. I was working for the EdTech vendor in a role that had left me in a vulnerable spot. The vendor had always kept their team small, and in reality, my role with them crossed several standard lines. I supported customer success, professional development, and even helped manage product development on some of their teacher-facing features. It was a role I loved because my hands were in many pots, but as I started to interview, it became clear that it was a role that was hard to define. I did not have one of those standard titles, and without that, it’s tough to get noticed. My experience as a teacher did not help that much either. While many EdTech companies want former teachers, the roles best suited for them (things like PD and community building) either did not have salaries that worked for my situation or had just dried up. EdTech just wasn’t this same anymore. I could see it when I went to conferences. Booths were almost all hardware vendors or massive companies that you had to buy into their whole portfolio. I could see it with friends of mine who had their jobs either eliminated or downgraded. Flip (formerly Flipgrid) is a great example. Microsoft decided to kill the product and make it a Teams feature. It also meant their whole team (who had built one of the best communities in EdTech) got laid off. The fact that Microsoft could not find a way to repurpose these notable personalities made the direction I needed to take clear to me. It is time to return to the classroom and return to my roots. While I learned a great deal at the EdTech company I worked for, I made a mistake going there. One of the many reasons I started as a teacher was for stability, and I let myself get to a place where that wasn’t the case. I let myself get lost there, but going back to the classroom has given me a new sense of purpose. I have landed at a great school where I can make a difference every day, and it's just in time to be on the sidelines with my son. After the chaos of the acquisition years, being in the classroom makes me happy. Many teachers feel like the grass is greener on the tech company side. I am here to tell you it isn’t. While the flexibility can be great, the instability makes it not great. The salaries aren’t necessarily better (I am getting a raise in the classroom.) The healthcare is better in schools. The retirement package is better in schools. You would think the pressure is less, but it is not. The overall stability is a huge reason to stay with a school system and work yourself up that way. So, you're saying it may be all bad with an EdTech company? No, but if you want to move onto the vendor side, I would measure if the juice is worth the squeeze. You only need to examine two factors: 1) Is there long-term stability? 2) Is this a position that can quickly transfer to another company? In retrospect, I should have answered no for both of those questions. The company I went to was a startup looking for an acquisition. While an acquisition can be lucrative, it also can be a significant hindrance as it goes south. You can also look at others challenges. Flipgrid ended as a feature in a Microsoft product with that whole team moving on. I knew almost the entire team at Nearpod before Renaissance acquired them, and nearly all of those folks have moved on. If you're looking for long-term stability, you can limit your search to just a few (Apple, Google, Adobe, Clever, ClassLink, Canvas, Schoology, and others). Even Microsoft isn’t necessarily stable, as their EdTech side recently went through multiple layoffs. I was also not in a transferable position. I did some of everything in the startup world, including support, PD, teacher community, LMS management, customer success, and even a little product development. It meant my title was unique, which was great when I was happy, but it killed me in the EdTech job search. You would think being involved in everything would help, but when competing against thousands of others, getting through the first culling of resumes is hard if an AI is just looking at job titles. If you want to go to the EdTech world, your best route will always be a revenue-generating position, whether direct sales or customer success. That just comes with a whole other group of challenges. If that’s the route you want, just make sure the company is committed (in writing) to giving you time to learn it. Looking back at my time, I will get value out of it. I can lean on my experience in support doing customer service as I work with parents. I have seen the other side so that I can deal with vendors more efficiently. I can help others by telling my story. I am excited to do all that while returning to my roots and doing something rewarding. I will even get to rebuild Big Guy in a Bow Tie. It’s time to get to work. |
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