Meet Nick Simon, District Partnerships at Goalbook
The start of Nick’s journey of working in education was in law enforcement.
Immediately after graduating from college, Nick worked as a Deputy Sheriff for the Milwaukee County Sheriff’s Office. Nick’s first assignment was at the Milwaukee County Jail, and one of his responsibilities was to work in the booking room, where he would interview everybody that came into the facility.
One question that he was required to ask was, “What is the highest level of education you have achieved?”
“Probably 95% of the folks who came through the door said 10th grade was their highest level of education,” Nick said. “So to me there was a super clear connection between finishing high school as being a differentiator between folks who end up in jail and folks who don’t.”
This experience really stuck with Nick and influenced him to explore a career in education. In this Q&A, Nick shares about his journey of working in education and then moving into sales for EdTech organizations.
1. What inspired you to go into education?
After working as a Sheriff’s Deputy, I moved to another state where I explored other job opportunities. Education drew me in based on the experiences I had working in the Milwaukee County Jail. In my experience, it seemed getting folks through high school decreases their chances of entering the criminal justice system. So I was inspired to give teaching a try.
I found a program at University of Michigan that allowed me to get my teaching credential and Master’s degree in a year. It was an intense year, but it allowed me to do my coursework and student teach at the same time. It was a lot of work, it was hard, but I got it done.
I got a job teaching U.S. History and U.S. Government at the high school level. I taught for two years before I moved states again, which forced me to look for a job other than teaching.
2. What attracted you to Goalbook’s mission?
The culture of Goalbook really appealed to me. When I started interviewing with Goalbook, I asked questions about the company’s culture because I was looking for something that was not like the large corporate culture that I had become tired of working in.
Every organization I worked for prior to Goalbook has a mission to help students in some respect and is trying to do the right thing in the educational space by creating things that are going to help teachers and students. But these organizations kept getting sidetracked because, in that corporate culture, the focus was on the next quarter’s earnings above all else. This made it very difficult to plan long-term because the best way to do something isn’t always the most cost-effective way. It became very hard to sell in that space, and I was tired of having to constantly make excuses for why the companies weren’t able to provide better resources or make pivots to meet customer needs.
The difference here at Goalbook is that it’s not just a mission statement — everyone here, even the executive leadership team, is very sincere about having a positive impact on the educational system. It really makes a difference that Goalbook is owned by its founders, and that it isn’t beholden to investors seeking a return.
I wanted to make sure the next company I was going to work for was mission-driven and somewhere that everybody who worked there believed in what they did and weren’t just coming in and cashing a paycheck.
3. What does your day to day look like?
Our work on the Partnerships team tends to be seasonal, so depending on the time of year, my day to day can be quite different. The throughline every day throughout the year is that there is always outreach or follow up. This means a lot of voicemails and emails, great demonstrations and conversations with district leaders, and following up with folks who have indicated interest in Goalbook Toolkit.
Conference planning is a huge part of the job as well. There is a lot of pre-planning that happens: from the logistics of the conference to choosing venues/activities for hosted events to working on co-presentations with partner districts for the conference itself.
During the spring and early summer, most of my work revolves around planning implementations and working with the Success team to ensure everything gets off to a good start with our new partners.
It is a great job if you don’t want to do the same thing every day because there is a lot of variety. And then you get to travel, talk to a lot of people, go to conferences, and see the differences in states as far as district priorities and initiatives.
“I’ve seen firsthand how using Goalbook Toolkit transforms instruction so all students succeed.”
4. In your eyes, how does your work support Goalbook’s mission?
Most of what I do revolves around introducing people to our work at Goalbook and having conversations with districts about how to improve the IEP writing process, transform instruction, and help students with disabilities.
Sometimes people are vaguely familiar with Goalbook, but most people, even if they’ve heard about Goalbook, don’t really understand what it is until they see what Goalbook Toolkit can actually do and how transformative it can be.
I see my role as showing district leaders how Goalbook Toolkit can change the lives of their special education teachers and students for the better. I’ve seen firsthand how using Goalbook Toolkit transforms instruction so all students succeed.
Just about every director I work with has told me a story about how one of their teachers has pulled them aside and thanked them for purchasing Goalbook Toolkit.
5. Was there a specific moment when you first considered transitioning to the private sector? How did you determine what role in the private sector would be best for you? Why did you think you would like that role and that you’d be good at it?
Circumstances forced me into the private sector, so leaving education wasn’t something that I did by choice, exactly.
I moved to another state, and at the time, that state didn’t have reciprocity for teacher certification. I didn’t really want to leave teaching, but the barriers to getting recertified in the new state and finding a job were too high. So I started sending resumes out to any education-adjacent company I could find.
I was pretty desperate at the time; I was putting my resume out there and seeing what stuck. One thing that I’ve learned in my career is that companies are always looking for salespeople. Salespeople come from all different backgrounds, and luckily, I was able to find a role in a company that supported education. I appreciate that I was given the opportunity to do sales not knowing whether or not I would succeed.
Honestly, I was very hesitant about getting into sales. A lot of people (myself included) have had bad experiences with pushy salespeople, and the idea that I would have to be one of those salespeople — and that my livelihood depended on me selling a certain amount — was pretty intimidating.
It was incredibly important to work for companies that sold a product I believed in. In the companies I worked for up to, and including, Goalbook, we’re not pushing something on others. We have a product that we think will help with X, Y, Z problems, and we have research to back it up. It’s a very consultative approach and not pushy. It’s matching someone’s need with something I can help them with, and I really appreciate the approach. It’s a lot easier to have conversations this way.
6. What advice would you give educators or former educators who are considering a role in sales?
A lot of sales is very similar to teaching. For example, if you have disengaged students, you have to find ways to engage them, and oftentimes, you can engage them just through making personal connections.
Most of what I do in my sales role is making personal connections and building relationships. If you have skills around building relationships with people, and if you want a way to still help educators out, sales could be for you because that’s how I view what I do.
Based on the conversations I’ve had and seeing people’s eyes light up when I do a demonstration of Goalbook Toolkit, I know Toolkit is having a positive impact on the folks who use it, especially the teachers who use it. So making people aware of that and seeing them go through aha moments doesn’t really feel like sales to me. It really just feels like problem solving.
7. What advice do you have for job seekers who are looking for a career change in general?
A barrier to me when I was looking for a job outside of education was that I didn’t know where my skills lined up.
So my first piece of advice is to figure out your core values and what you want out of a job. Do you want to work for a large company with a lot of resources? Do you want to work for a smaller team where you might have to think on your feet?
When we’re looking for jobs, I don’t think we talk much or think much about a company’s culture or values. I think that’s something more people need to ask themselves. That’s not something I learned about until I was working at companies where I didn’t like the culture.
If something is important to you, you should be comfortable asking about it during interviews.
One thing you can ask any interviewer is why they work there? That was something I asked, and I think it goes a long way of seeing how people feel about their jobs and gave me a lot of good insights.
Be empowered to ask questions. Interview the company you want to work for. At the end of the day, it’s a partnership or relationship between you and the company. If one person isn’t happy in that relationship, no one will be.
“It just feels like a special place to work, and I’ve never worked at a place like this before.”
8. What are one or two things you love here at Goalbook?
Top two: the people and the people.
I have a theory that 95% of job satisfaction comes from not doing the job itself, but from the people you work with and your direct manager. Having great relationships with colleagues and with managers is really what sets Goalbook apart from anywhere else I’ve ever worked.
We are a very unique company in that everyone is mission-driven. There is no one I don’t feel comfortable going up to and having a conversation with, knowing that we have alignments on believing that the work we’re doing is positively impacting students and helping special education teachers and educators in general. There are not a lot of places that I’ve worked where everyone is aligned like that.
I feel like everybody that works here are some of the nicest people in the world. You can have a conversation with anybody about anything. Everyone is understanding and so genuine. And it doesn’t feel forced at all.
It just feels like a special place to work, and I’ve never worked at a place like this before. Having this kind of culture is not something that just exists independently. I know it’s something that has been worked on over the years, but it is making a difference.
9. What is your favorite memory during your time at Goalbook?
Goalbook used to fly people out to San Mateo, CA for a full day of interviews if they made it to the final stages, so when I was in the final steps of interviewing for my position, Goalbook flew me out for a day.
I really wanted to leave a good impression, but I was having trouble deciding what to wear. This was my big conundrum. Typically it’s a no-brainer: I would wear a suit and tie and not think twice about it.
But, it was clear that Goalbook was a different company. It was kind of like a startup in Silicon Valley and a techie-type of atmosphere. And nobody on any of the video calls I had been on had been dressed up formally. I really didn’t know what to do.
I decided to err on the side of caution, and I opted to show up at the office wearing a suit.
I walked into the office for the interviews and looked around, and of course everyone was in jeans or shorts and t-shirts. I felt so out of place because here I was showing up in my suit.
We took a break midday to go for lunch, and the team was nice enough to take me out to eat. There we were, sitting at the restaurant with everyone in their casual clothes but me in my formal clothes.
I joked, “I’ve got to tell you all — I’m embarrassed and I feel like I overdressed. I feel like I’m everyone’s dad taking you all out to lunch.”
That got a big laugh, and it gave me a sense that everyone had a sense of humor.
At some point over my five years here, everybody that had attended that lunch has told me their first memory of me was me showing up in that suit. While I was embarrassed about it at the time, it was nice to find out later that they all appreciated that I took the process so seriously. I just wanted to put my best foot forward.
It’s something that is funny to me now, but at the time I was super embarrassed.
10. What are you reading/watching/listening to right now?
I’m a bit of a gamer, so most of my media time is playing a video game called Baldur’s Gate 3. It’s basically a computerized version of Dungeons and Dragons.
11. Early bird or night owl?
I’m flexible. I don’t have a tendency one way or the other.
In my household, I’m usually the first one up with the kids, so I’m up early. I can function at a pretty high level very early in the morning. I don’t particularly like doing it, but I can do it.
On the other hand, I can stay up late and be fine. Sometimes I’ll be the last one up, and that doesn’t bother me.
So I don’t neatly fall into one of those categories.
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