Mark Phillips is the founder and CEO of HireEducation, a recruiting agency that fills open EdTech positions with qualified candidates! We discuss the right and wrong ways to message recruiters on LinkedIn, how the stress of an EdTech job feels different than teaching stress, and how teachers can maximize their potential when applying.
In your experience, what are the most natural paths that teachers can take from the classroom into EdTech?
Professional development or training is probably the biggest “gateway drug,” or most teachers’ first step into the industry. This role used to be called per diem training or education consulting. Big publishers would close a deal and slap on some Professional Development as part of the contract, and hire former teachers to lead those sessions. It’s a great fit for teachers because you get to talk to and empathize with other teachers; your job is to demonstrate what best practices look like for your product or service.
Another large category is curriculum & instruction, or actually building out the content. That’s what teachers already do! They’re developing lesson plans for their classrooms, or maybe they’re on committees that do this on a larger scale. Eventually, this path can lead to design-focused or process-focused roles in product or project management.
Next is sales, which is a big umbrella. Most teachers start their sales career as a Sales Development Representative (SDR)or Customer Success Manager (CSM). At some companies, the CSMs are also responsible for implementation and training, and there isn’t a dedicated professional development team.
There are some former teachers that are in marketing roles, but this can be harder to break into. Maybe you join a startup where everyone wears a lot of hats, show some results on the Marketing front, and now — boom! — you’re a Director of Marketing. In my experience, the other path for teachers interested in marketing is to leave the classroom to get an MBA or other type of credential and then come back to EdTech with that new training on top of your teaching experience.
What advice do you have for teachers who can’t decide which of those options appeals to them most?
When I lay out the options, 90% of the teachers I talk to say, “I never want to do Sales.” I have a couple of responses to that:
First, I tell them that EdTech Sales is not about being Rodney Dangerfield; it’s not the used car salesman icon you have in your head. Sales is very different in education because it’s empathetic. If you walked into a district or university and tried to be manipulative, you wouldn’t get anywhere. Sales cycles are too long, and districts’ hands are tied in lots of ways. You’re not handing someone the pen and saying, “what’s preventing you from signing now?” You’re building relationships and usually working fairly long-term, complex projects.
Secondly, if a big reason you want to leave the classroom is financial — if you need more money for whatever reason — you really need to think about Sales. In Sales, you get paid for results, so if you’re good at it, you will outpace your current earnings quickly. You could make the same money in your 2nd year as a Sales Rep that you would make after 15 years in other EdTech career tracks.
Most teachers I talk to still aren’t interested, but for those who are, I make sure they have realistic expectations. The companies where a teacher is going to get the broadest, deepest, most meaningful experience are often startups. In those environments, though, there’s going to be outside money involved from angel or venture capitalists, and those funders expect sales numbers to stay high. I don’t want to paint a rosy picture because there will absolutely be pressure. An EdTech salesperson has to accept the pressure from above without applying that pressure to the teachers or superintendents they work with — they have to broker that tension, and it’s tough.
Does that mean you would not recommend Sales to someone who is leaving the classroom for mental health reasons?
I haven’t been in a classroom, but I have to imagine the stress is lighter in Sales. The stress level of teaching is part of why it can have such an adverse effect on your mental health, but I also think it’s because you can’t tangibly see benefits. Think about the overcommitted teacher, the one who spends hours making sure every kid knows each learning objective. Maybe she can celebrate with the parents if a student meets an IEP goal, but she doesn’t get to ring the gong because the deal closed, you know? Even though Sales is stressful, there’s a mental health benefit to saying “I did this, so I got that.”
Let’s talk about the actual job search process. What mistakes do teachers make when choosing which jobs to apply for?
There’s a lot of wishful thinking that goes on. I would venture to guess that 75% of the people who apply through our website are teachers. Since all of our jobs are posted on our website, they might find and apply for VP of Product or CEO roles and say, “Well, I have 20 years of experience.” And I’ll tell them (nicely), “not in Product Management! Actually, you have zero. If that’s a path that really interests you, let’s talk about where to start.”
And on that point, I really do recommend startups to teachers who want to accelerate their career growth. If you join a startup with 5 people, you might be getting everyone coffee on Monday and putting together a board presentation on Friday. That’s the kind of environment where you’ll build new muscles.
What does a “good” resume look like for someone who is transitioning out of the classroom, and how do teachers get this wrong?
Teachers spend a lot of time talking about their qualifications and their responsibilities, but the corporate world expects results. It’s hard, since you’re working with kids: you’re dealing with real human beings that are forming. You can’t quite say, “I had a 1 million dollar quota and I brought in 1.4 million.” But still, the best teacher resumes I’ve seen include bullet points that quantify impact. If you were paid based on your results, how would you justify your wage? That’s what you should ask yourself when you write your resume.
Secondly, everyone has multiple versions of their resume, and that’s okay. Teachers often feel there is one single truth they have to maintain or convey. That’s just not true, especially if they’re open to different kinds of roles like Product or Marketing or Sales. You’re going to have to use different language to appeal to people in each of those silos. As a teacher, you’ve touched hundreds of lives. You have a robust set of experiences, and you should be able to highlight different parts of yourself to make sure your resume is relevant to the type of job you’re applying to.
What are the best strategies for actually securing first-round interviews?
First, it’s totally reasonable to apply to tons of jobs if you want to — I don’t begrudge anyone that. You can send out tons of resumes in an hour, and maybe something turns up. Let’s say you went to Loyola University and volunteered for Worldwide Wildlife Fund in college, and the person who opens your resume happens to have those things in common with you. Affinities are real, and that could be enough to generate an interview.
Still, I wouldn’t make that my primary strategy. I would adopt the perspective that relationships matter. You’re going to get a job that interests you if you reach out to people! The EdTech field is full of phenomenal networkers who are really mission-driven. You can very easily create an affinity by demonstrating that you care about the same things they do. So sure, apply to as many jobs as you want, but then do some LinkedIn searching to find out who the hiring manager is for that job and invest in that relationship.
I think a lot of people get stuck on that last part. From your perspective, what is the right way to send a message to a recruiter or hiring manager on LinkedIn? Should you be upfront if you just applied to a role at their company?
Keep it short, a couple of bullet points. Think about the emails you would read. Literally, the first part of my day is moving my inbox from 350 down to 50. That means I’m trying to archive and move quickly past 300 things, some of which might be job applications. Nobody is going to scroll through what you write. Paragraphs suck. Have a sentence and a couple of bullet points.
Let’s say I’m applying to Freckle and see a job for an Account Executive. I send my resume and don’t feel like I got the opportunity to really show my personality in my application, so I think, “how can I show them how awesome I am?” I go to LinkedIn and I see you recently posted about your transition from the classroom. I might write something like, “Hey Lindsay, I’m considering the next step in my career. I see that you were a teacher and you’re no longer a teacher. I’d love to know your secret. By the way, Freckle looks cool!”
I’m not telling you 100% that I already applied, but I’m also not just saying, “Hey Lindsay, let’s be friends.” I’m giving you context and establishing that I’m preparing for a change. There’s an old phrase that says: “If you want money, ask for advice. If you want advice, ask for money.” Teachers can find job opportunities by asking for advice and looking for affinities. What do you have in common with the person you’re messaging? Don’t be afraid to ask for 30 minutes of their time to interview them about their experience.
Do you ever tell teachers not to leave their jobs?
Yes! For example, retirement benefits are a huge consideration. Lots of teachers think they could make 60k now vs 100k in a different job. Maybe, but you won’t get the retirement benefit you would get if you’ve been teaching for 15 years. Most states have excellent pensions. Leaving is not always a good decision, especially if you’re getting close to retirement.
How would you advise a teacher who is nervous about sacrificing their impact by leaving the classroom?
I’ve encountered enough former teachers in enough environments to know that you can work your way back to having an impact. Maybe you sell back-office software like Student Information Systems, but you know you’re saving teachers six hours of time each week. There’s your mission…it’s not hard to fan the flames of mission in EdTech. Sure, you have to understand that you’re in a business, and that businesses succeed because they are well-run and capitalized and have strong leadership. They won’t just succeed because of their mission. But you get to feel like your work is really making a difference, too.
And then you start to find other things that are fulfilling about the work. The feeling of “hey, I built this,” or “I got this community effort going with my team.” I’m a headhunter and a Sales guy who puts companies and people together, and I love my work and feel super mission-driven. It’s about discovering a new way of defining “mission” for yourself.