Jeremy Schifeling has devoted his career to helping students succeed in theirs. From recruiting top students at Teach For America to leading student marketing for LinkedIn, he’s touched the lives of millions of people just starting their journeys.
Along the way, he’s published a top-selling book on job applications, served as the University of Michigan’s tech career coach, and produced the most-viewed video in LinkedIn’s history. He currently leads teacher outreach efforts at Khan Academy and shares his thoughts on Break into Tech, a site for anyone who wants to launch a tech career.
Describe how you got your very first marketing role. How did you know marketing was a good fit for you?
My very first marketing role didn’t have the word “marketing” in it — I was a recruitment fellow at Teach For America. The nonprofit sector has lots of weird titles, but my job was really to market teaching and TFA to college students across the country.
I took the job after coming out of the classroom and was super engrossed in the work — I was losing track of time and working late into the night because I wanted to, not because anyone told me to! I felt like I was in my perfect flow state and wanted to replicate that. All throughout my career, I’ve come back to marketing roles because they are a great match between my personal gifts and the opportunities presented by the working world.
What aspects of marketing did you find most compelling in your first role?
It’s all about knowing yourself! I loved the idea of having a massive scale. I was a 21-year old kid who had been a Kindergarten teacher; all of a sudden, I was reaching out to hundreds of thousands of students at once and they were signing up in droves for something I had put on their radar for the first time! It felt powerful in a way that teaching in an individual classroom didn’t always feel.
How would you describe marketing to someone who has never heard of the field? What types of people make strong marketers?
A core skill in marketing is having empathy for several different audiences. First, you need to have empathy for the pain of your users. This looks like doing research before a product is launched and really taking the time to understand why students are struggling or what districts need.
Once you have an inkling of what you want to build and how you’d like to solve users’ problems, you need to have empathy for your cross-functional peers. I’ve never been a Product Manager or an Engineer or Designer, but I was thrust into working with them! I needed to understand their goals and pain points, especially when they differed from my own.
Finally, there’s the campaign piece. If you understand why someone is suffering, what are you offering that’s better? How can you present a vision that compels your audience to notice you and take action? If you can do that really well — like a lot of teachers already do in their classrooms — then you can be a great product marketer.
Which aspects of that came most naturally to you?
Building engagement and running campaigns came naturally to me, since I was always doing similar things in my classroom. I built a classroom blog in 2004 — back when people barely knew what blogs were — because I wanted to reach out to families and reassure them their kids were in good hands.
If you’re talking to a teacher who has less marketing experience than you did when you made the switch, what short- and long-term actions would you recommend they take?
My first piece of advice is counter-intuitive: get off of Lindsay and Jeremy’s blog! People read interviews like this one and think marketing sounds great and glamorous — but then once they get into it, they realize it’s not what they were looking for after all. To combat that, definitely reach out to people who are in your “second degree network.” Maybe you think you don’t know any marketers, but there’s probably someone you know who knows someone who is a marketer.
If you can get in touch with that person through your mutual friend, you can start to figure out what a marketer actually does all day. What’s the nitty gritty, and what do they hate about their job? This allows you to play devil’s advocate with this hypothesis of a new career. You can also find people on LinkedIn by entering “Marketing” and “2nd degree connections” into the search bar!
In terms of actually going for it, the honest truth is that it will be tough to go directly from teaching to product marketing. A lot of the time, these roles are reserved for people from business school or with experience at peer companies. To catch up a bit and test your hypothesis even further, it makes sense to experiment with marketing skills in a safer context. You could start your own blog or help a friend market their ideas — this allows you to kill two birds with one stone because you gain confidence that you’d actually like a marketing career, and you can show the recruiter a portfolio of marketing work that you’ve done.
That’s super helpful advice — it might be intimidating to tell someone to “do marketing,” but telling them to “write something and share that with an audience” is so doable, especially with the tools at our disposal today! What were the biggest challenges you faced when you attempted to break into tech?
I discovered in hindsight that my biggest challenges were internal. I had a little voice in the back of my head that said things like, “Tech is for techies! You’re not a techie, so you don’t belong.” When I ultimately broke in, I realized that not only was I able to do it, but there were thousands of people in tech from totally different backgrounds (like education and liberal arts). I realized I had wasted 10 years by not believing it was doable. Imposter syndrome is so pressing, but it’s not always based on data.
How did you overcome that little voice in your head?
I learned more about the other side of the hiring equation. I ran interviews & read resumes for some of the nonprofits I worked for. Eventually, I realized the job search isn’t an SAT test with a right and wrong answer; it’s all perception. And one of the first things you learn as a teacher or a marketer is that you can shape perception.
That gave me the confidence to try. If I have to convince a recruiter or hiring manager that (for instance) I can reach an audience, work well with others, and demonstrate excellent results, I know I can tell my story in a way that shapes perception.
What are some of the biggest misconceptions people have about working for a tech company?
I think there are two levels to the misconception that you don’t belong: the first is that you’re not even going to be considered. Then, maybe you know that most people at tech companies aren’t engineers, but you still assume they must learn how to code once they get in.
In reality, most people at tech companies are not spending any time with code. If you peel back the layers of why companies like Remind or ClassDojo or Clever are successful, it’s not just because their engineering is beautiful or elegant. It’s because they understand teachers and students, and know how to sell and market their stuff.
How do you think EdTech is similar to and different from other tech companies?
When you apply to Google, you’re thinking to yourself, “I can’t wait to tell people that I work at Google!” That feels great for like five seconds, but then it wears off and you might not actually like what you do every day. People focus so much on the brand or the idea that they don’t really focus on what the company is like on the inside. EdTech has that same siren song, and it can get you smashed on the rocks like Odysseus!
The reality is that the education industry — like video games or entertainment — is much harder than other industries because it’s attractive. Everyone wants to improve education. The buying incentives are perverse and there are many different end users, from districts to students to families.
On the other hand, if you go after a non-EdTech space like accounting software, you know you’re not getting into it for the brand or the industry — you’re doing it because you love the craft and what you’d actually be doing every day. It’s also a pretty clear sale; the same people who have the pain points are the ones buying and using the software.
That’s tough advice, especially since so many teachers are passionate about continuing to make an impact on education.
Look, there are big advantages for teachers thinking about EdTech, because you have domain expertise. You could hire a Product Manager who studied Computer Science at Stanford, but they’re going to have a steep learning curve when trying to understand education (compared to a teacher who could hit the ground running on day one!)
Still, loving the domain only takes you so far. If you work for a product that is great in theory but no districts or teachers or students actually want to use it, then you’re probably not going to enjoy working there.
That totally makes sense. In your opinion, does it make more sense for a teacher to pivot into a role they are less excited about at a company they love, or hold out for a role in the field they want to be in long-term?
It’s totally possible to move horizontally in EdTech companies. Once you’re known to the Product or Marketing Team, for instance, it is pretty easy to put yourself up for a new role.
With that being said, if you’ve totally underperformed in your customer support role because you hate answering tickets every day, it’s going to be hard to make the case that you should be a Junior Product Manager! I go back to my “flow” comment from earlier — I prioritize the hours that I spend on this earth. If I’m going to spend 10 hours a day at a job, I want to love as many of those hours as possible, even if I don’t have a particular passion for the product.
What does the typical work day look like for you now, as a Senior Product Marketing Manager at Khan Academy?
At Khan Academy, even though we are 10 years into the organization’s growth, we are still talking to teachers every day or every week. Whether I’m just corresponding with them over email or doing something more formal like an interview or focus group, we’re trying to figure out what they actually need — especially since education changed so much in the past year.
Next, I’m getting in the trenches with the product team. We’re reviewing insights together and figuring out what this means for our roadmap: where do we need to go in the next year and the next three years?
Last, it’s all about the campaigns! Product roadmaps are pretty long. As a tech outsider, you might think, “I’m going to come in and launch a cool new feature that I would have loved in my classroom.” But then you realize that building a feature can take 6–12 months! In marketing, though, there’s always a campaign you can run on a shorter timeline. For example, I brokered a partnership with Headspace, and now Khan Academy is holding a virtual meditation retreat for teachers after a tough year. It might not be as life changing as a new feature, but it helps us position the Khan brand as something teachers can count on.
What initially drew you to Khan Academy?
Again, know thyself! I took the nonprofit sector for granted when I was younger. Working in NYC, I would see these attorneys and bankers on the subway and figure they must be so much smarter and more effective than I was in my nonprofit job!
Eventually, though, I realized that there are a lot of uncomfortable incentives that come from working at for profit companies. Even in EdTech, you have to ask yourself… who’s really the stakeholder here? Is it the teacher? The district customer? The shareholder? You can only serve so many masters. One of the things that attracted me to Khan was that as a non-profit, I had the freedom to focus on teachers first and foremost.
How can teachers screen companies to identify those that are genuinely teacher- and student-focused?
Understanding the business model really helps. As a teacher, you’re generally shielded from that and just handed the software. But take examples like IXL and iReady. IXL definitely has a district sales team, but they have spent tons of time selling directly to teachers. On the other hand, iReady almost exclusively sells to districts, and therefore has totally different incentives.
Knowing what the company’s north star is — asking the hiring manager, “how are you held accountable? What does success look like to your boss’s boss’s boss?” — will help you make informed decisions and decide if you’re comfortable with those incentives governing your work.
Any other advice for teachers who are considering making a transition?
This is true for all industries, not just technology. The number one thing is to take action. The job search is intimidating and rejection sucks. But there is something empowering about not being trapped, not feeling like you’re just being pulled toward my destiny. Whether it’s talking to a friend who left the education space, or who’s doing the job you might want to have next. Taking a baby step gives you the psychological freedom to know that you’re in control of your own future. If you do decide to go for it, it gives you a little bit of momentum for the rest of your journey.