I talk to tons of teachers who I know would make excellent EdTech account managers AND sales reps: you’re empathetic, driven, strategic… and maybe a little competitive, too 🙂
But which customer-facing path is right for you?
If you’ve asked yourself this question before, you’ll enjoy this interview with a former teacher who tried both! Brooks Dougherty taught High School Science before taking an entry-level support role at Edmodo. From there, he managed a Customer Success team before pivoting again to an entry-level Sales role. Today, he’s a successful Sales leader at BetterUp, a coaching platform that helps organizations provide personalized development and coaching for their employees.
Q&A with Brooks Dougherty
Describe your teaching experience. What did you find most rewarding and most challenging about being a teacher?
I taught High School Biology and Environmental Science at a small charter school in San Jose.
The most rewarding part was definitely the relationships I built with the students. I still keep in touch with several of them and it’s been incredible to watch them grow into successful adults. At the time, I loved seeing them make baby steps of progress or choose to navigate situations in healthy ways.
It felt good to be there for my students beyond academics, as a role model and someone in their life they could come to for support. I also coached basketball and it was awesome to do things with kids outside of the school day – those experiences still stick with me.
The most challenging part was the extreme amount of work. I don’t know if it’s the norm, but in my charter school I had very little support and had to create my curriculum from scratch. Every night, I was up late lesson planning and prepping for the next day – it was hard for me to “turn it off” because you could always plan more and do more for the students in your classroom.
It was also challenging to deal with the somewhat unforgiving nature of kids. They don’t care that you stayed up late; if you’re not on your A game every day, it’ll go off the rails and they’ll run over you. You don’t always get to reap the rewards of your hard work.
Was there a particular turning point for you, or a moment that made you decide to leave?
Not really; I was toying with the idea of continuing until the very end. It wasn’t an easy decision – the challenges I described were very real, but so were the rewarding parts. Every semester, I felt myself getting better. After my first year I was like, “I’m going to be SUCH a better classroom manager this time around!” And that keeps going – the desire to see progress was really compelling.
Ultimately, though, I knew that I didn’t want to be a lifelong teacher. I wanted to explore and develop other skills. I finally figured I might as well try something new and see how it goes!
What options did you consider when planning your first step after teaching? How did you find your first role?
I was looking into a few different things. Number one was actually going back into the classroom at a different school. I also considered circling back to environmental science. That’s what my degree pointed to, and I had an opportunity to get a job in that field.
The third option was an EdTech position at a company that hired lots of other Teach for America alumni. Looking back, the people at the company helped me make the decision – I was excited to join.
What did you know about tech & EdTech going in?
I didn’t have my eyes on EdTech at all. It was more like, I want to try something new and see what happens. I realized this job would provide a lot of learning opportunities and seemed like the right environment to explore.
I used a little bit of EdTech in the classroom. My charter school saw themselves as an R&D lab for experimenting with innovative classroom technologies. They used a very basic formative assessment app called Exit Ticket. We each got a set of 30 iPods (yes, iPods!) and I could just create quizzes in there and then review the data. The app developer spent a lot of time in my classroom, so I got to see behind the scenes of what building an EdTech product was like. I definitely found that interesting and leveraged it in my interviews, but I wasn’t “all in” on EdTech.
What was your first role, and what was your transition like?
My first job was at Edmodo. The title was “Teacher Advocate,” but really it was a Customer Service role. Me and a team of other former teachers manned the support inbox; that was most of the job. In addition, we got to be the voice of the user inside of the company and advocate for teachers because we were so in touch with their complaints and feedback.
I never thought I wanted to be in Customer Service, but it was my foot in the door to get into tech and led me to everything that followed! I like to tell teachers that it doesn’t matter what the job is as long as you like the product and the company because you’ll learn a ton, discover pathways you’re more excited about, and gain the experience and the tools to start moving in that direction.
I found there were a lot of skills from the classroom that made me successful in my first non-teaching role. The first one was hard work. I quickly realized if I worked the same amount I worked as a teacher, I would be a superstar here and have my weekends back!
Secondly, communication – I knew how to convey things in a simple, user-friendly way. As a teacher, I was always trying to get on the level of my 9th graders and understand what they needed. It’s the same principle when working with customers – you need to meet them where they’re at.
I love that Edmodo took the ideas and advice of former teachers seriously. Since some companies are better at this than others, can you think of anything you noticed about Edmodo during the interview process that helped you determine this?
The amount of teachers at the company really stood out to me. The customer support group was about 10% of the company and they were all former teachers. It showed that the company cared about listening to that voice. In addition, “caring about teachers” was definitely part of the company’s brand – they had a lot of positive buzz for that reason, and you could even tell from the way the website framed their mission.
I would advise teachers to understand a company’s public perception and look around when you’re interviewing; how many other teachers does the company employ? Talk to those individuals if you can.
How did you end up in Sales?
I ended up managing the Customer Support team at Edmodo, then slid laterally to manage their Customer Success team. Customer Support was for all of our users (free and paid), but Customer Success focused on our few paying customers. Still, both roles were in the same realm of “existing customer management.”
Then a friend of mine told me about Front Row – they only had 20 people at the time and were looking to hire a Sales Rep. I applied because I had been at Edmodo for 3 years and had gotten to that same point where I wanted to take a leap and learn new skills. I was nervous about going into Sales, but I knew I liked the people, the product, and the mission. I was also excited about being at a smaller company – this would help me take what I learned at Edmodo and help an earlier-stage organization grow. That was the challenge, and Sales just happened to be the role.
Now that you’ve worked in both Customer Success and Sales, what do you see as some of the key differences? How might a teacher decide which path is a better fit for them?
I think the main difference is that your work is cut out for you in Customer Success. You know who your clients are; you have a very dedicated and defined group of people you’re there to support. They’ll come to you asking questions, you’ll have recurring meetings with them, and to some extent they’re willing to talk to you. If you want to come into work, know what you need to do to be successful, and go home knowing you did a good job, go with CS.
In Sales, the whole world is your oyster – the whole patch is your account. No one’s trying to talk to you, and you need to generate those conversations. There’s more creativity but also a lot more failure and a lot more rejection. The lack of definition can be anxiety-producing and stressful. You’ll have weeks where you feel like you’re doing a bad job because you’re not getting results.
If someone was trying to pick, I’d ask – how’s your ability to handle stress & rejection? Do you like completely unstructured problems? But also, what’s your take on flexibility? If you want to index toward flexibility, sales is good.
Honestly, sales is a complete roller coaster. You get out what you put in. It’s not stable – there’s a low floor and high ceiling. It’s really exciting when you get a win, and there are months where it’s miserable. I have an even-keeled, bigger picture perspective on things which helps.
Do you think you cultivated that or is it your natural personality?
A little of both! I definitely still have to remind myself to stay positive when I’m getting unmotivated. I do like the aspect of being able to work on my own time, implement my own strategies, and ultimately get the rewards. In that sense it’s kind of like teaching because you have ultimate creative control. No one really knows what you’re doing in your classroom; you can do it your own way. It’s an art! There’s an aspect of that in Sales.
So at this point, do you think you’ll stay in Sales for the long haul?
My favorite part of Sales is actually meeting with prospective customers and helping people solve problems. I like that more than the analogous parts of account management, where you’re getting “in the weeds” rather than focusing on the bigger picture and vision.
On the other hand, I don’t love prospecting in the way some sellers do. I would certainly go back and do Customer Success for the right organization at the right time. For now, though, I’m happy doing Sales.
What does your day-to-day look like now, as a Sales rep at BetterUp?
My day-to-day is pretty similar to when I was starting out in Sales. I divide my day into buckets: having meetings, trying to get meetings, and then learning (upskilling, PD, researching the product or prospects). Either I’m doing one of those three things, or I’m wasting time.
When you’re hiring an entry level Sales rep, what qualities do you look for? What red flags do you watch out for?
The number one is hard work and resilience. Tell me about a time that you failed miserably and what you did afterwards, because that’s going to be, like, every week.
I also look for someone’s ability to backwards plan from a goal. Are you systematic about how you’ll achieve something? That’s very transferable from teaching.
I want to know if you can be simple, concise, and compelling. There are so many interviews where people talk on and on without a point. This is an instant red flag because if you do that with a prospect, you’d waste their time.
Lastly, you can’t overlook competitiveness – when you see other peoples’ success, does that make you want to win?
What advice do you have for teachers hoping to transition into EdTech?
Don’t be picky about finding your dream job right off the bat. Look for a company where you feel good about the mission and team, because those are the fundamentals. If you’re aligned with what the company is doing, you’ll enjoy it and learn. Even if it’s not your ideal job, you can move internally.
I would also say that there is no shortage of EdTech companies out there. Cast a wide net when you’re looking around. Go to company websites and see what they’re hiring for. That will give you a better idea of the types of roles that are out there to discover what gets you excited. As you do a lot of that you’ll start to see commonalities and patterns that will help you update your resume.
Look, it’s such a tough time to be a teacher — I have mad empathy and sympathy for anyone teaching right now. I talked to someone yesterday who taught for five years and is unemployed by choice because of the stressors of the pandemic. I encourage everyone to look at EdTech and go for it if it excites them.
But also… I do genuinely believe things will get better. Next year has to be way better than this year. It’s hypocritical of me, but if you’re not over-compelled to leave the classroom, keep it going – we need good teachers. I try to stay hopeful.