Developing a Business Mindset

Chrissy Cantore’s Journey From Special Education Teacher to Customer Success Manager

Before you made the transition to the private sector, what were you doing?

I taught for six years as a special education teacher and coach. For half a day, I was working with students; the other half, I was coaching other special education teachers. In addition, I was the special education liaison for our district. I would go to trainings and come back to turnkey that information through professional development sessions for my team.

What was your number one concern when considering leaving public school to be a Customer Success Manager in an edtech company?

My biggest hesitancy in applying to the Customer Success role was that I thought it would be “sales-y” when it came to talking about money. I was worried about having to “wheel and deal.” I think I asked every person I talked with during the interview process about the sales piece. Although I had some concerns, I ultimately knew that I believed in Goalbook and how Toolkit would enormously help SPED teachers.

As I continued to learn more about the role, I came to peace that even if there were moments in the role where I needed to have challenging conversations about budgets, they are necessary in order to get the Goalbook resources into the hands of teachers who will greatly benefit from them.

Now that you have been in your role for nearly two years, has it felt too salesy?

In the role of Success Manager, those sales conversations are with school leaders whom you’ve built a relationship with. It does not surprise them that they need that renewal conversation. Often, they reach out and ask to start chatting about next year. It’s a natural next step since we worked all this year together and now it’s time to think about next year. It seems like it fits and isn’t a separate piece.

During renewal conversations, it doesn’t feel like I am pushing something that they don’t need. Even when you’re trying to expand an implementation, you know that more people would benefit from this. It never feels like your goal is to get more money out of people.

What were those first days of being new on the job like?

During onboarding, and even now, I’ve had the chance to work with different members of my team and other teams across the company to broaden my understanding. My teammates were so open to being helpful and knew they had a responsibility with onboarding to make sure I felt prepared for those conversations. I was also surprised about how often people reached out and wanted to help and offered additional support beyond our scheduled meeting times. Of course, I learned a ton from working directly with my manager! When it came to getting comfortable with the sales/renewal components of my role, my manager has been a great mentor.

What do you love most about being a Customer Success Manager?

Goalbook’s research studies and digging into the data to see the direct impact that our schools are having has helped me feel the most connected. When Goalbook implementations are fully successful, it can have such an enormous impact on teacher efficacy and student performance. This knowledge really motivates me to best support the implementations that I am leading.

In hindsight, what has been the biggest shift in your transition from the public sector to the private sector?

For me, honestly, the biggest difference in working in the private sector is seeing things way more “big picture” than just what is in front of you that day. When I was in the classroom, I was working directly with students. On a day-to-day basis coaching teachers, we focused on “what do we need today? what do we need this week?” and much less of a “how is this going to impact the entire year and years looking down the road?”

I think that mindset has really shifted for me in the business side of my current role. It’s not “what does this account need right now” or “what do I need to support my team right now”, but “how will that better support us over the next quarter, and, over the next year, what are our goals looking ahead?” This is just like backwards planning as a teacher, which is so important when thinking about working with individual school districts.

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