Why Educators Should Consider Sales Roles

Thank you for reading the EdSkipper, Skip’s newsletter about skipping from education to education-aligned careers. Every Saturday, I send out a list of curated remote jobs. Premium subscribers receive two additional emails a month with industry insights and advice to help you apply more competitively to the jobs you’re passionate about.

When I started the database project sourcing every job that is looking for educator/edtech experience at 250-300 edtech companies, I noticed a very clear trend: about 20% of the jobs I posted every week were sales roles.

Some sales roles were looking for current teachers or administrators, others for former teachers a year or two into their first edskip, and still others for experienced industry professionals with 3-5 years experience. In other words, everyone!

Sales is a promising career pivot because the entry-level roles require no direct experience selling. Companies look for candidates with the soft skills necessary to connect with their audience as well as the temperament to handle rejection. Early career sales representatives receive extensive onboarding and training so companies look for the right fit more than specific industry knowledge or experience. (Though experience using that product or competitors is helpful!)

But, most of us cringe when we think about sales jobs. (If you missed the poll I conducted asking if people were interested in sales roles — 75% of respondents said no!)

Some of this is because we’re so used to bad sales pitches: pushy, spammy, aggressive, annoying, intrusive, and so on.

My husband and I recently bought a new car (our first ever new car), and I was really surprised about how helpful the sales reps were. They showed me features I needed to know about, answered questions, didn’t push the sale, didn’t even bat an eye when we turned down all the financing upsells, and so forth.

Of course, that’s because I didn’t realize they save their insistence to convince me to service the car at the dealership. In fact, they’ve called or texted half a dozen times in 4 months. They don’t seem to hear me when I say it’s not convenient for me to come to their shop — there’s one 30 minutes closer to where I live.

And this is what we usually think of when we think about sales: sales people who start with their needs. These are the folks who make you feel vaguely uncomfortable – like you’re being scammed or there’s going to be a catch or an unending pitch or they will just never stop calling.

But edtech sales is different!

And it’s more similar to what you do as an educator than any of us would expect.

Good sales is centered around solving a customer’s problem (because it’s a good product that genuinely helps them out). It’s about listening and active questioning.

Sound familiar? It’s because we do these things too. We call them: identifying or adapting resources by assessing needs and facilitating conversations.

This is exactly why educators are often really good fits for sales roles – and can find it rewarding (not just financially, though it definitely can be that too!). 

What’s in this issue:

• Why Edtech Sales is Different from Pushy Selling

• The One Sales Role Every Educator Will Like!

• A Sales Dictionary: (premium subscribers only)

  • BDR? Inbound Sales? Field Sales? Acronyms & Jargon Explained

  • OTE: Typical Compensation Packages for Sales Roles

• Entry-Level and Mid-Level Sales Opportunities

• How Do I Sell Myself for a Sales Role Without Any Sales Experience? (premium subscribers only)

  • Includes a sales-specific skills analysis quiz (96% say these quizzes help them understand their skills better)

Why Edtech Sales is Different from Pushy Selling

Edtech sales is different from a lot of traditional B2B (business-to-business) sales. Schools and districts are often strapped for cash and so products must be strongly outcome-driven and solve meaningful problems. (They heal a shark bite not a minnow nibble.) So a product pitch needs to be carefully tailored when selling to schools rather than a product that’s purely B2B. 

For example, if you’re selling photocopiers, the business’s goals likely don’t impact your sale. Each business likely has similar pain points too: their existing copier has broken or is hard to program. But every business needs a photocopier so your pitch is more about selling your specific photocopier over the competitor’s.

But if you’re selling an educational product, you have to understand what’s happening in that specific school or district, what pain points come from that, and then be able to show why your product will solve those problems. There are certainly general trends between schools — high absentee rates, declines in post-Covid test scores. And there are similar solutions — professional development, additional tutoring, personalized curriculum. But schools are also collections of people which means that what works in one place needs to be adapted to work somewhere else.

You need to build a different kind of sales relationship: you have to understand each school uniquely and be able to translate your product to their needs. This involves a lot of asking questions but also tailoring sales presentations to different types of districts – large urban districts, small rural ones, private schools, etc. and then even more granularly to their particular needs.

A sales rep in edtech (aside from the most entry-level positions) is speaking regularly with teachers and school staff and connecting with them based on shared experiences and a passion for solving the right problems. The selling part comes by persuading them that the product you have is the product they need because it helps them teach their students better not because they need to replace their existing solution.

If you love to solve problems, connect people to the right resources, explain why this product is the right fit, that’s also what you’d be doing in sales.

The One Sales Role Every Educator Will Like!

Most of you are probably like, ‘I could do all that except for the persuading part.’ Shudder! (Don’t worry — I shuddered too. Sales is intimidating!)

Like any department, sales departments consist of employees who do the bulk of the selling, those who manage the department, and a coordinator who organizes the department. Sales departments also have two roles that are well-suited for educators: sales trainers and sales engineers.

I’ll talk about sales trainers later because it’s a role that requires sales experience. But sales engineer roles, despite the very scary title, are often looking for educators and administrators!

A Sales Engineer is a SME for the sales department — they’ll explain product features (traditionally these were uber technical hence the ‘engineer’ in the title) to the sales team and help them craft the right messages to sell the products. That means they regularly assist with sales presentations — both through the preparation stage, making sure the details are accurate and make sense to an audience, and during the sales call where they are on hand to answer more technical questions.

Don’t let the ‘engineer’ part of the title scare you away. Edtech companies don’t have highly technical products so they call on an SME who understands their clients — recently transitioned educators or school admin!

In the past month, I’ve posted several of these jobs on the main job board: a Solutions Engineer at Instruction (looking for school or district admin experience), TeachTown was hiring a Program Enablement Specialist (with counseling/BCBA experience), Age of Learning was hiring a National Curriculum Specialist, Math (with district admin experience), and Amplify was hiring a Product Specialist, Literacy (with teaching experience).

I also posted one in the database — Classlink’s Sales Engineer (with teaching or higher ed experience) role. It’s still listed on their career page but I posted it on January 25th so they are probably interviewing candidates right now. (Some recruiters keep a job open and scan new applicants as they come in; others set an expiration date but only look at them until they have enough candidates to interview; oh, and others leave it on their career page for months so investors think they’re hiring. YMMV.)

As you can see, job titles are not consistent but don’t let the ‘engineer’ in a role necessarily lead you to think you need a software, techy background!

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