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From Teaching to Sales

Eric Sarb taught Middle School Math and Science for 6 years and is now a successful Sales Manager at Renaissance Learning. Still wondering why you should listen to him? Well, he breakdances and has a punk band — how could you not trust a guy that cool?

What was your teaching experience like?

I started teaching in Chicago through Teach for America (TFA). Initially, I assumed I would just do it for two years and then go into urban and regional planning (my major in college), but I fell in love with teaching! I knew I at least had to see my 6th graders graduate, which would require staying for a third year. I continued to fall more in love with the job over the next couple of years and thought I’d stay in the classroom for at least a decade.

How did you ultimately make the decision to leave the classroom?

By the end of my 4th year teaching in Chicago, I felt really burned out. I moved to San Francisco and found a charter school teaching 7th grade Math and Science that was basically the opposite of my school in Chicago: it had different teaching and behavior management practices and smaller class sizes. Despite all these differences, teaching was still the hardest job in the world. I came to the conclusion that I might not be able to do it forever.

At the end of my fifth year I knew I wouldn’t be able to make it much longer, but I’d put so much work into creating my curriculum and getting to know the school, it felt silly not to stay for another year. By October of my sixth year, it didn’t feel like a decision anymore… I just wasn’t able to find balance or set boundaries on how much work I was doing. It was very clear that I needed to leave.

What non-teaching careers did you consider, and how did you narrow down the list?

I asked myself what kind of broader impact I wanted to make in education, and what type of leader I wanted to be in the fight for educational equity. I was lucky enough to be part of a TFA fellowship called the Rising Leaders that specifically helped alumni answer these questions. I did a lot of reflecting and strengths-finding exercises, and that really helped inform what I wanted to do next.

Based on my experience as a teacher, I knew I wanted to help make the work more sustainable for other educators in high-needs areas. I narrowed it down to two different options: I could work in policy, because policy-makers could change things like class sizes or the length of the school day to increase equity and sustainability, or I could work in EdTech, which gave teachers tools to make their work more manageable.

How did you actually find your first job after teaching?

I thought about my network. Friends who worked in EdTech turned me onto EdSurge and the jobs board there, which was really helpful. I looked for job descriptions in all parts of education and highlighted the parts that sparked my interest. I went to an EdSurge jobs fair and put my resume in a Teach for America pool.

Thanks to the resumé pool, someone from Freckle Education (called Front Row at the time) reached out to me. When I visited the office for the first time, I sat down with someone who worked in Sales and someone who worked in Curriculum. Based on the work I had done to identify my strengths, I knew I needed to be people-facing. It was clear to me that Sales was the route I should take, since I never loved lesson-planning as much as I loved teaching those lessons.

I was hired as Freckle’s very first Sales Development Representative (SDR). SDRs talk to people who are not decision makers and do a lot of cold calling in order to identify potential sales. At Freckle, that looked like talking to all the teachers who said they were interested in the Premium version of our product and then doing targeted outreach to districts.

What new skills did you have to learn as an SDR? What surprised you most about the job?

I needed to learn how to use Salesforce, which is a customer relationship management system (CRM). This allows you to track opportunities and accounts, move them through different stages in the Sales cycle, and attach potential revenue to each one get a sense of your progress toward Sales goals.

But honestly, what surprised me most is that I didn’t feel like there was anything I needed to learn in order to do my job successfully, beyond the skills I already had developed as a teacher.

My experience in the classroom informed my conversations with teachers about their needs, and my understanding of school leadership structures allowed me to find out who was making purchasing decisions (and what type of relationship the teacher had with that decision-maker).

As a teacher, you’re constantly listening to students to determine what they understand and need, and that skill is directly transferable to your customers in Sales.

What do you think it takes to be successful in a Sales role? What kinds of people are probably not a good fit?

It takes a desire to serve and help people solve problems, which I know all teachers have, as well as a natural curiosity & good listening skills. People look at Sales as a manipulative job: salespeople have to put on a “show” to wow the customer, and based on that performance, you get the deal. In fact, Sales is all about the customer, and getting to understand their struggles and needs. Listening is actually more important than talking.

Beyond that, you have to be energized by talking to people and getting to know them. If you can’t imagine communicating with strangers all day, then you’re probably not a good fit for Sales.

What role do you have today, and how did you grow into that?

I’m currently an Inside Sales Manager at Renaissance Learning (Freckle was acquired by Renaissance about two years ago).

Honestly, I just got there one step at a time! I was first promoted to an Account Executive (AE), a closing role that carries a quota. As an SDR, you’re charged with identifying possible opportunities and then setting up meetings for the AE to run. The AE works to close the sale and get the decision-maker to sign the contract or deliver the Purchase Order.

From there, I got promoted to Senior Account Executive (SAE) by consistently hitting my goals. After the acquisition by Renaissance, an Inside Sales Manager role opened up on my team. I always knew I was interested in Sales Management because I had benefited from strong managers and wanted to help other people grow as sellers.

What does a typical day look like for you now, as a Sales Manager?

These days, I might meet with my direct reports in one-on-one meetings to understand what’s going well and what’s challenging for them. My job is to make their jobs as easy as possible. I really like when I get to observe my reps on customer calls because it keeps me close to the customer and we get to debrief afterward to discuss growth opportunities.

I also spend time in Sales Management meetings with other leaders, where we discuss changes in our Sales processes, upcoming marketing initiatives, or our team’s progress toward monthly or quarterly benchmarks.

What do you look for when hiring for a Sales role? What would make a candidate stand out?

I look for preparation: at Renaissance, applicants are always given a role-playing scenario in advance. They have the opportunity to build a presentation or outline how the customer call should go, and it’s always obvious when candidates take the time to prepare. I look for passion: they should care about the products and the mission. For former teachers that’s almost always the case, but it’s not a given. Last, I look for the ability to listen and respond appropriately based on the needs of the customer.

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

  • First, find a company with a product you truly value, and you’ll never feel like you’ll have to try too hard to sell it.
  • Second, don’t be afraid to take an entry-level role to see how it feels, and then grow from there. You might not like it, but the only way to find out is to do it.
  • Finally, I wish someone had told me to be confident in my ability to do other types of work based on the skills I used in the classroom. I truly believe that classroom teachers can do 90% of other jobs because you are planning, executing, and responding to the needs of others on a daily basis, and that’s what a LOT of other jobs require.

If you’re thinking, “I want a job just like Eric’s…”

Start here:

  1. Make a list of 5–10 EdTech companies with products you love. If you’re stumped, play around with EdSurge’s product index to see what’s out there. Then you can use Google to find the Careers pages for those companies.
  2. On any major jobs board, search for “Sales Development Representative,” “Business Development Representative,” or “Account Executive” roles, and avoid anything with “Senior” or “Manager” in the title. Note that “Account Executive” or “Account Manager” roles may or may not be entry-level; it’s important to look at the job description to see if they expect several years’ worth of Sales experience.
  3. Once you find roles that seem promising, practice networking. Join LinkedIn groups like this one. Connect with current or former employees of that company who also work in Sales. Remember to introduce yourself with a short note when you make the connection, and don’t be discouraged if you don’t hear back from everyone.