How to Get Out of Teaching and into Sales

It’s June. Graduation excitement is in the air. The students are excited for their summer and the teachers are asking themselves how to best utilize the few short weeks of freedom that is often over exaggerated by the masses. And for any teacher that has a renewal contract in hand, they are asking themselves, “If not this, then what?”.

Through a series of unrelated events, two friends put me in touch with two of their KIPP teacher friends who are humoring the idea of leaving. Both are in pushing 30 years old. Both have respectable years under their belt. And both feel the same weight of the question; If not this, then what?

A lot people ask me, “Patrick, how did you get out of teaching and into enterprise software sales?” Actually, no one has ever asked me that. But these two KIPP teachers were actually interested in some kind of sales job and did pick my brain on how to get into sales. This is my advice.

First let’s get some things straight. There is a vast spectrum of what sales even is. You have door to door (D2D), business to customer (B2C) and business to business (B2B).

  1. Door to Door is your cable provider or your solar panels. From what I’ve learned from peers who do this type of sales, it’s a volume game that rewards a certain style and personality and the number of doors that you’re willing to knock on. I have a lot of respect for these people because it terrifies me.
  2. Business to Customer is cars, electronics, etc. It’s when a customer comes to the seller and is shopping around. You have to convince one person that the product is for them and they decide on their own if it’s worth it.
  3. Business to business is when one business’ offerings are sold to another business. These sales are complicated. They’re often multiyear contracts. It’s based on some sort of proven ROI or there is a proposal evaluation process. This is where multimillion dollar contracts are signed and a lot of people have to buy in. This is the lay of the sales land.

I didn’t plan on going into sales but after a few years I can easily see why I found a route in this profession. Teachers naturally sell. They sell ideas. They sell solutions to problems. They sell inspiration. They sell motivation. Selling means getting someone to buy in. In the modern business to business world, it takes 6.8 people to say “yes” to the decision before a purchase. How often does a teacher have to come up with a value proposition to sell an idea that causes buy in from a group of people? EVERY 10 MINUTES. If you’re a current teacher, let’s think about a specific situation we’re in often. A student/parent/department chair/principal has a problem. They come to you and you take a seat in your classroom. For the sake of this example let’s pretend it’s a parent. You start the conversation by saying “Ok. It seems like we have some things to discuss. What’s on your mind?” The parent across from you begins to speak about the struggles of their student. They say things like “My student used to like reading and now their grades are dropping.” You say “Yes I imagine that’s very frustrating. Tell me more about their situation so I can better understand.” And before long you are learning about the student’s lack of sleep, how they recently got their heart broken for the first time, how the parent is working more and the student is responding poorly, how the parents are recently divorced, or whatever combination of events is the “why behind the why” the student is struggling. Now that you know the “why behind the why” you can actually sell the parent the solution that actually makes sense. Good sales people find the fit for the customer and then get the customer to convince themselves of the route they should take. I’ll talk more about these types of things in a follow up post. Now that we know teachers have a natural fit in sales, let’s talk about there to start.  

Let’s first get an understanding of the typical hierarchy of a sales team. Since I come the B2B software sales world, this advice will be focused on that. At the beginning we have Business/Sales Development Reps. They’re called BDRs or SDRs depending on the convention of the company. These folks are the ones who generate leads for the sales team. Some companies outsource this and the entire jobs is to read from a script and call hundreds of people a day. There are quotas on the number of calls you make and the number of meetings you set. Personally, that sounds really awful to me. The TV show The Office actually provides a great framework for this. If you’ve seen the show all the way through you may remember when Michael Scott has to take a second evening job at a call center. It seemed awful. This is outsourced BDR. What is MUCH MUCH BETTER is an inhouse BDR team. This is where you are setting meetings for your own company and your own teammates. You’re trained internally and have a career path with the company. Even if you don’t stay in sales you’ll be able to pivot once you’re in. This was my first job out of teaching. Typically the compensation is based on a split model of a base salary plus commission. My first BDR job had a base that was the same as my teacher pay and I had the opportunity to double the salary if I hit quota each month. I didn’t know how realistic hitting quota would be but I hit it more often that not. This is a pretty high paying BDR job and I got a bit lucky for my first go round. Often times you’ll see roles where the base is around $30k and the OTE (on target earnings) is typically double the base so you have the opportunity to make $60k if you become a high performer. A mandatory question if you’re interviewing for this role is to ask how many people hit quota. The company will almost always say a majority of people and they can lie to your face. I’d recommend asking someone on the team itself to get a realistic picture. A second important question is if the quota is capped. If it is, don’t work there.

The roles after BDR in a traditional structure would be mid-market sales or inside sales (ISR). In The Office example this is Jim and Dwight. They sit at their desk and make sure they have calls with prospective clients and they get the paperwork done. You typically don’t travel and you’re dealing with mid sized companies or middle tier sized contracts. Every company is different. In this role your commission is based on what you sell compared to the BDR role where your commission is simply setting up a meeting.

The next step is account executive or outside sales. Every company is different so it’s impossible to look at a title and know which type level it is but this is when you hold big meetings, travel, have big clients, and sign big contracts. These are generally the most lucrative roles. In the software world, these people can have a base salary in the low six-figures with and OTE ranging from $200k to $300k. Obviously these sales jobs are found in major cities but often can be remote since companies want their sales reps to be living in the territory where they sell. That means you can land a job where you work from home and make six figures but there is a component of travel. For some people this means a flight and a night in a hotel every week. My job has peaks where I  travel every week for a month and I spend 8 nights in a hotel. You get used to it but it’s not my favorite. These types of roles require major discipline in time management. Do you think a teacher would have a hard time managing themselves? I laugh at the thought.

So how do you get into sales? For this post I’m going to assume most teachers would have to start in the BDR role so I’m going to focus on this for my tips. The first thing I would do as someone that is wanting to get into entry level sales is read two books: The Lost Art of Closing and Rejection Proof. These two books will get you in the right mindset of the job and demonstrate what you need to know for the interviews. So what happens in these interviews? First, there is almost always an HR call where they screen the candidates. They want to know how you sound on the phone and how serious you are. This is why reading the books is critical. You can’t look like you’re testing the waters with your job application. Be a student of sales so they know you’re legit. There is an assumption in the market that lots of teachers humor the idea of quitting every year but they don’t actually do the proper things to stand out. I asked my old boss who hires people monthly about what teachers (and anyone else for that matter) should be doing to get the job.

  • What are the first things you look for in a first time BDR applicant? I’m looking for someone with curiosity, the ability to deal with a bit of ambiguity, detail oriented, excited about life and the potential to grow. I ask myself, “Can they pick themselves up quickly after being disappointed. Are they willing to try things that might make them a little uncomfortable?”
  • What could teachers do to help themselves stand out in their resume? What can do they do better on the first screening call? The candidate should highlight the times they had to sell an idea or use their creativity to transform something. I would also make sure they have a really good cover letter explaining why they want to move out if teaching and into sales.
  • What are some major mistakes you see people make who are trying to break into sales? There are sales muscles that you should flex the interview process allows for those to naturally be demonstrated. So often people don’t do sales like things during the process like following up after an interview, asking good open ended questions in the interview, and closing the deal.

Once you get past the initial interview, there is often an assignment associated with the process. You’ll be asked to write a mock email and leave a voicemail. They may even go so far as to schedule a 5 minute call with you to see how you handle yourself on the phone. The assignment portion is where they test your basic skills but it’s also testing one important asset of a candidate; how good are you at research?

Here is an example of the email my KIPP friend sent as part of his interview process:

Hi Ms. Jones-

I’m reaching out from XYZ company, a restaurant management software company, to set up a time for a call.

I had the pleasure of stopping by one of Abuelo’s locations in Austin last week and noticed there was some confusion around the availability and price of some menu items. I’ve seen restaurants at similar growth stages struggle to accurately update inventory, causing challenges with tracking available items and forecasting food costs. Fortunately, many restaurants have leveraged our software to streamline their inventory and vendor management systems.

Since you oversee inventory and operations, I’d like to grab 15 minutes of your time to discuss streamlining your systems, and if anything, I can give you a better idea of how to minimize losses and keep those tables turning.

Thanks so much for your time (and that tasty Durango Burrito),

Patrick Frasier
XYZ company

Another part of the assignment is leaving a voicemail. I give the same advice to every BDR on how to speak to executive assistants or how to leave a message. The key comes from the book The Lost Art of Closing in the concept of a value trade. The other important aspect is to call as if you’re equally important to the other person on the phone and have the tone of voice you’d have if you were setting up your own doctor’s appointment. Most of the time it goes like this.

“Hi. My name is Patrick and I’m trying to get a hold of Melissa. Is she available by chance or does she prefer to set phone calls via appointment?”

“Hi Patrick. She’s not available but what is the purpose of the call?”

“Ah ok. I work with similar company/industry/positions to help them with X problem and I’ve actually never met Melissa. I was hoping to set up a call to share what the strategies other people are deploying. It should only take about 30 minutes and it will teach her some new things. Do you control her calendar?”


This last question is important because it tells you who is in control. You’ll get various responses like:

“Yes. Send me an email with the purpose of the call and I will review it with Melissa and get back to you.”


“No I don’t. Your best bet is to just send Melissa an email.” or

“Yes. Melissa is free next Thursday in the afternoon”

For the purposes of a mock call- you’re most likely going to leave a voicemail and it should sound similar to the above script.

“Hi. My name is Patrick and I work with XYZ and I’m calling to set up an appointment with Melissa. I work with X company to help them with Y problem and I’d like to discuss that with Melissa. At the very least, she’ll get educated on some recent advancements used by others. I can be reached at ###-####. I’m looking to book a phone call sometime the last week of May.”

Now record yourself saying this script. Listen to it. If you’d hang up on yourself because you sound like a dumb sales person then try it again. That’s why I say to sound like you’re making a doctor’s appointment. Booking a doctor’s appointment is business as usual and your voice should reflect that. People are trying to determine if they’ll open the door for you and if you sound like someone that normally enters their home, the door will open.

Now hopefully you’ve gotten past the first couple of rounds of interviews. If you get past the assignment round then it’s basically about personality fit. I think most teachers don’t have to worry about this part. Teachers navigate awkward conversations and can be responsive to the dynamics of a room. More importantly, teachers are light on their feet. In my final interview for my first sales job, the vice president of sales did a one on one interview with me. About 15 minutes in he says “Ok. I’m going to be someone on the phone and you’re calling me. Ring ring. Hello.” I damn near threw up. But what do you do when a situation breaks out in the classroom? What do you do when you get an unexpected hard question? You spring into action and don’t even think about it. The VP wasn’t even testing my ability to properly answer the questions he threw at me. He just wanted to see if I could keep my cool. I only remember one smart thing I said in that mock call. When asked a question I didn’t know the answer to I said “That’s the crux of exactly what I want to set a meeting about. I can put you in touch with our subject matter expert on that.” Really I was deflecting but it’s the type of deflection that then puts the actual experts in the room together.

Another question I get asked often is what questions people should ask in an interview. One of my bosses always told me that the best questions to ask were the ones you didn’t know the answer to. You’re talking a company you barely know. Find out more. Who are their competitors? What’s the market like? What’s the hardest part of the job? How do they treat professional growth and development? What’s their philosophy on employee reviews? These are great things to discuss.

So now you’ve finished with all the interviews and you have a job offer. Here are some things to be careful about with offers.

  1. Get a base salary that is reasonable for you. Even if you make less for a month or two, know what the upside is after you get your groove.
  2. Make sure people actually hit quota within the company. can help you with this investigation.
  3. Do they have call quotas? What is it? Is it reasonable?

My advice at this point is that the first job out of teaching is a launching pad to your future. It in no way represents what you’ll be doing 2 years from now. Teachers can have a hard time with this. After your first year of teaching you get an idea of what life could look like 20 school years later. That’s not how the rest of the world works. Take a job that provides you with opportunity and people to learn from. And if six months from now it isn’t working out, you can pivot again. The second time will be easier. You’ve already opened the doors.

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