From Teaching to Customer Success
By: Transitioning Teacher
Tags: Edtech, Teaching, Career Change, Customer Success, Interview

Paige Pollara is a former High School English teacher who transitioned into Customer Success at NoRedInk, a startup that builds stronger writers through adaptive practice, writing exercises, and assessment. Paige shares which parts of her career switch came naturally to her and which parts took more effort & patience. She also breaks down the open Implementation Specialist role at NoRedInk and gives insight into how she evaluates teacher resumés so you can optimize your application!

What did you love most about teaching? What was hardest for you?

I loved a lot of things about teaching. First and foremost, I loved building relationships with my students. 9th and 10th graders are such interesting little people — they’re trying to figure out who they are and who they want to be, and I really loved being a part of that process and getting to be a resource for them.

As an English teacher, it helps that I’ve always been a huge fan of reading and writing (and young adult fiction in particular). It was fun to be able to recommend something like Percy Jackson and see a student’s eyes light up as they realized reading was fun. That aspect of the job was always super rewarding.

The hardest part for me was work-life balance. I was a perfectionist, and constantly found myself tweaking and improving my lessons the night before. I was also drowning in the amount of grading that I had to do. I worked nights and weekends because I wanted to leave comments on my students’ work, and I had 130 to 150 students! The amount of pressure I put on myself to be an excellent teacher was just too much, and I eventually burned out.

How did you know it was definitely time to leave the classroom?

I had four different principals in four years of teaching. It was really hard to do my job effectively when each year, somebody came in with a new vision of how things should be done.

In addition, I realized I really wanted more feedback and professional development. Because I was doing well and my class wasn’t on fire, I was mostly left alone and no one came to see me. In some respects that was great — I had a lot of autonomy, so I got to try and fail in a pretty safe environment. In other respects, this left me feeling like I didn’t have the resources to go from being a good teacher to being a great teacher.

What other job options did you consider, and how did you narrow them down?

Like a lot of teachers, I believed my first role would be something related to curriculum or instructional design. I applied to a number of those roles and just didn’t hear back. It was a big bummer and really disheartening at first. I tried to shift my mindset away from looking for the “ideal role” and toward the companies themselves: What companies would I be really excited to work for? What products are making a huge difference in teachers’ lives right now?

That’s such good advice, especially because you can network so much more authentically if you actually feel passion for the company’s mission! How did you find NoRedInk, and what was the interview process like?

I loved NoRedInk and saw they had a Customer Success role open. I didn’t know much about the role (or Customer Success in general), but the job description said something about supporting schools and teachers. That seemed like something I could do, so I applied even though I was a bit skeptical I would meet the qualifications.

However, the first recruiter call went really well. Many of the components of NoRedInk’s interview process were skill-based (for instance, I had to deliver a sample training and send sample emails to customers). I was able to show up and show the team what I was capable of — and in the process, I gained confidence that I would enjoy the role, because I was already doing some of it!

Think about your first few weeks at NoRedInk. Was anything surprising to you?

Building relationships with teachers and administrators came super naturally. At the end of the day, all of us cared about helping students become more confident writers, so we could come into a conversation with the same end goal. It also helped that I had used NoRedInk in my classroom before joining the team. Because of this, my product onboarding felt relatively smooth and I could focus more on the technical aspects of the job.

One thing that surprised me: I learned my email language needed tweaking! I wasn’t concise enough and showed too much emotion. I had to cut down on the number of exclamation points I used in writing.

Time management was also tricky. As a teacher, you’re so used to being rushed to fit your work into a specific period of a time. In my new job, I had so much more autonomy with my schedule. I wasn’t used to having multiple tasks with ambiguous deadlines, and it was a steep learning curve.

What helped with that over time?

Practice, and not being afraid to ask. That’s what your manager is there for, and why you have dedicated time with them each week. Just asking the question, “What’s the highest priority right now?” can help you direct your energy toward the right things. I still do that!

How did your role evolve at NoRedInk over time?

I joined NoRedInk when we were a small company (about 40 employees). There were a lot of opportunities for growth, and I took as many as I could! I spent a year and a half in Customer Success and moved to a team lead role on this team. I really enjoyed the strategy and process management this required. Eventually, NoRedInk noticed there was a need for a dedicated implementation team to support our larger customers. This seemed like the perfect mix of supporting teachers and project management. I jumped at the chance to be a founding member of that team and was promoted to manager after about a year.

What would you recommend to others who hope to make internal switches in their company?

I see a lot of folks do this at NoRedInk: someone on the Sales team moved to Marketing, two people from Customer Success went to Implementation, and we had a User Researcher move to Product Manager.

If you see opportunities to pair with people on other teams, take them! For instance, I spent time with folks on Product, Curriculum, and Marketing to learn about their goals and how my team could support theirs. This helped me learn more about the company as a whole.

Today, you’re looking for more Implementation Specialists to join your team! What is an Implementation Specialist responsible for at NoRedInk, and what does a typical day look like?

At NoRedInk, customers are assigned a Customer Success Manager who is ultimately responsible for the account. The largest and most complex accounts also have an Implementation Specialist; we are accountable for their training and resources, and we use our ELA instructional expertise to help them integrate our product with their curriculum. Currently, each Implementation Specialist has about ten accounts that we work with and know super well.

It’s hard to say what a typical day looks like because it totally depends on the time of year!

In July through October, Implementation Specialists can be found on calls helping clients set expectations, coordinating trainings, and following up with resources that schools need. They also spend time actually conducting virtual trainings so that teachers can use the program effectively.

In November through December, we pair closely with our partners in Customer Success to track usage and customer engagement. We develop intervention strategies for our at risk accounts and partner with Product or Marketing to create touchpoints for teachers.

In January through March, we help teachers navigate their second semester by providing more training and continuing to check in to make sure they have what they need.

In March through June, we’re rounding out the school year by planning for the back-to-school season, managing projects and initiatives to deliver in July, and partnering with Sales to create implementation plans for new clients.

What do you think it takes to be successful in this role? Who might not be a good fit?

You need to have teaching experience. As many teachers will tell you, there is nothing worse than a Professional Development session led by someone who has no experience doing what you do. We need educators with real experience integrating technology into their classrooms so that teachers feel really confident in their implementation.

What makes some teachers’ resumes jump to the top of the stack?

I would highly recommend sitting down with some of the job descriptions you’re interested in and mapping your teaching experience to those bullet points. For instance, in Customer Success, you need experience helping customers along what’s known as the “customer journey.” I remember looking this up when I applied and realizing it’s just backwards planning! You identify an end goal and determine what steps it will take to get the customer there. I had backwards planned hundreds of units; I knew that my students had achieved the goals and outcomes I had designed.

It helps applicants stand out when they can give me core examples of how they’ve already done some of the things we’re hoping they’ll do in the role.

Backwards planning is such a brilliant example! Can you think of any other non-obvious correlations between teaching experience and customer success jobs?

Job descriptions often emphasize the importance of data-driven outcomes, maybe framed in the context of portfolio management (hitting quotas or renewal goals). Still, teachers are all about data-driven instruction, and they have proof of their impact. They can talk about the students who passed end-of-year tests or the interventions and supports that got them there.

Even though this isn’t revenue-driven, it’s still a totally valid example of the same skillset.

Who might not be a good fit for a Customer Success role?

You have to be a people person. You’re “on” a lot of the time when you’re training. If you felt drained and exhausted from the feeling of having to perform as a teacher, it’s good to be aware that Customer Success has some of that, too.

I’d also recommend looking at the specific niche the company is looking for. For instance, do they need someone with Math expertise? Spanish expertise? We see awesome teachers apply to our Implementation Specialist position without English experience, and that’s a bummer because we need you to be an ELA expert.

Anything else you wish someone told you when you were first preparing to leave the classroom?

Two things stick out to me: first, I didn’t realize how competitive the EdTech world was until I stepped into my first jobs fair and there were hundreds of hopeful people vying for the same few positions. I had to wait in long lines to talk to people, and it was scary — I wasn’t ready for it. Be prepared for that and be patient. Your role will come!

Also… you’ll miss your students. The first, second, even third fall… you’ll hear about your teacher friends preparing their classrooms or doing parent-teacher conferences, or you’ll see your old kids start to graduate and you’ll miss it. And that’s okay.

What helps you feel confident that you made the right decision? Do you ever think about going back?

Someone on our team recently went back into the classroom. She missed her kids, and that was real! For me, though, I love that during trainings I get to watch the lightbulbs happen with teachers. I recently observed a teacher, showed her a new activity, and in the next class she was already excited to apply it.

Maybe I’m not helping the same group of 150 kids, but I’m still able to make an impact and help kids become better writers, to have a voice, and to advocate for themselves. That makes it worthwhile for me.