Dan Carroll is the Chief Product Officer and co-founder of Clever, a digital learning platform that brings all of a school’s EdTech applications into one secure portal and provides single sign-on for everyone. Before starting Clever, Dan was a Middle School science teacher and then Director of Technology at STRIVE Prep in Denver. We discuss how he solved problems in the classroom, why he ultimately built Clever, and how his teaching experience made him a better leader & entrepreneur.
Tell me a bit about your teaching experience. What initially drew you to the classroom, and how did you decide it was time to leave?
I started teaching through Teach for America. My first year was amazing but also incredibly overwhelming — I was so overwhelmed by lesson planning and grading, I barely had time to sleep. I started to get my feet under me during my second year — I was able to build great relationships with my students and get them excited about science.
Even as I was making some progress, it was clear to me that classroom teaching was not the way I could have the most impact at my school. I was surrounded by phenomenal educators — and I knew that even if I stayed in the classroom for decades, I’d never get to their level!
But I did notice that I could be really helpful with technology. I started using my school’s neglected laptop carts and had success bringing tools like PhET digital science labs into my classroom. And I noticed myself solving problems outside of my classroom. The wifi would stop working so I’d spend some time after school fixing it, or the email server would go down and I’d ask my network leaders why we weren’t using Gmail. My principal must have noticed, because as our network expanded, she asked if I wanted to step into a new role as Director of Data & Technology.
I took that job and loved it. I could have an impact on students in a much bigger way and support my amazing coworkers at the same time. I had a big vision for how my network could use tech to make teaching and learning so much better, and I was ready to spend five or ten years bringing that vision to life.
Did you start building Clever in your capacity as Director of Technology, or leave in order to start the company?
A little bit of both. As Tech Director, I could think of 10 or 15 different problems I wanted technology to solve, from supercharging family engagement, to helping ELL students build vocabulary, to eliminating the slog of hand-grading exit tickets. I started the job thinking I would solve one of these problems each month; in reality, it took me a whole year just to run my first pilot!
There were a few reasons that the pilot took a year, but the biggest one was data integration. Every new EdTech app was another data silo, another custom roster excel file I had to create and upload, and another username and password for teachers & students to forget. I realized there was no way I could be innovative or make EdTech seamless for teachers and students until I solved the data integration problem.
I started running around the country to find someone who had already figured this out: someone had to have built a platform that would allow me to innovate and bring new tools to my students. I started a meetup in Denver & Boulder for EdTech people. I joined every online community I could find. And I even went to visit a handful of innovative schools in the Bay Area that I’d been reading about online. Nobody knew the answer, but they all validated that this was a real problem that someone was going to have to solve soon.
At that point, I was kind of ready to wait for someone to do it — I mostly felt relieved I wasn’t the only one who saw this missing piece of the EdTech ecosystem. But as I was visiting the Bay Area, I was sleeping on my friend’s couch, and he insisted that we were the ones who needed to solve the problem. So that was the beginning of Clever in 2012!
After a weekend of planning with my friends Tyler and Raf, I went from Tech Director with a problem to startup co-founder building a solution. We had such strong conviction that this was the right problem, timing and team — everything just seemed to fall into place. I asked my school what kind of transition plan would make sense, and they asked me to stay through the rest of the year to help hire my replacement. So I juggled two jobs until the summer, when I moved to San Francisco to work on Clever full-time.
In the early stages of building Clever, did you notice yourself applying the skills you learned as a classroom teacher?
Absolutely. Every day. During the first few months of starting Clever, one of our biggest jobs was sharing our vision: demoing to schools, pitching to investors, presenting at Demo Days & conferences. For many of my peers, this was one of the most terrifying things they’d ever done. But for me, I had stood up in front of a room of thirty 8th graders with no idea how to teach, so this was nothing!
Public speaking turned out to be just one of many things that were easier as a startup founder than as a teacher. Being a founder is challenging and you have to make personal sacrifices, but it was nowhere near as grueling or intense or emotionally difficult as being a first-year teacher. That experience toughened me up and made me feel I was ready for anything. No one in the business world could throw me a bigger curveball than my 8th graders did every day!
I think about this when hiring, too. I don’t believe that classroom teachers are the only people who can work in EdTech, but school experience is certainly a superpower. Having trained hundreds of people at Clever, it can take a really long time for a non-teacher to have full empathy for our users and a deep understanding of the reality of being in a classroom. For new hires at Clever who haven’t been teachers, I often help them find a teacher who will let them sit in the back of their classroom and observe. After a few days of observation, the new hires start to understand the nuances that are hard to explain, like, “Why can’t teachers just pull out their phone and reset a student’s password during class? Or, why can’t the teacher just call our support team right away when they have an issue?” Those kinds of things just aren’t possible in most classrooms, and that takes a while to build that nuanced understanding.
There’s no way we could have built Clever without my experience as a teacher and a tech director.
As Clever’s product leader, what challenge are you most excited about right now?
This has been such a hard year. The teachers, administrators, and families we work with are all so overwhelmed, exhausted and worn down… and many of us at Clever feel the same way. Whether that’s from being sick or losing family members, or even just the whiplash between school closures, and openings, and closures, it’s been the most challenging year many of us have ever faced. And in the midst of these challenges, everyone in education has had to grow, pivot, invent, and learn to an extreme degree. We know that healthy change comes when we have time to reflect, space to experiment, and room to grow. This year, we’ve had to change more than ever with none of those resources!
And throughout all of these challenges, I’ve just been blown away by the people in the education system, especially the teachers and district leaders I’ve had the privilege of working with. They’ve dug deep and shown superhuman grit, tenacity, and leadership to make sure students can keep on learning. I’ve heard leaders tell me they discovered skills and energy they didn’t even know they had.
That’s what gets me most excited. Obviously we all wish COVID didn’t happen, but among all of these challenges, I keep hearing people talk about a few amazing innovations or ideas that have emerged. I’ve talked to teachers who refused to use their online gradebook before COVID, but now rave about that amazing app that helped them engage with their students remotely in amazing ways. I hear CTOs talk about a 5 year 1:1 device rollout plan that got successfully completed in a few months.
That gives us a much stronger EdTech foundation. As things go back to normal, we’ll bring those innovations back to our normal lives, and we’ll know we’re capable of far more than we ever realized.
Let’s shift to talking about current teachers who are hoping to transition into EdTech. What advice do you have for them?
My two biggest pieces of advice may seem contradictory at first.
On the one hand, go broad. There are tons of EdTech jobs these days, so apply to lots of them, and don’t be discouraged by a rejection email. It can be hard for companies to differentiate between teacher candidates: teaching resumes can look really similar! So apply to everything and play the numbers game.
On the other hand, when you have the time and the perspective, go really deep. If you’ve been using Freckle for a few years and you became such an expert that you led a PD session on the tool, you are an insanely valuable applicant to that company. In this case, you might want to do more than just apply online and hope for the best. Build relationships with the trainers, success managers, or support members that you interact with. Share amazing product feedback & suggestions. Talk about how much you love the product on social media.
And as you’re impressing them with your super sharp classroom perspective, make sure to listen carefully to understand what life is like on the “other side of the fence.” Try to figure out the company’s priorities, the tradeoffs they’re making, and the reasons the product doesn’t work the way you’d like. If you can build those kinds of relationships and add that kind of value, you just might find the company reaching out to recruit you!
Does that imply that teachers who hope to transition into EdTech should be strong EdTech users first?
Absolutely!! First, work on being an EdTech leader at your school. If you can show strong examples of EdTech leadership, that will help you in the application process and give you the confidence you need to succeed in interviews.