In this episode of The Teacher Career Coach Podcast, I sit down with Andy Rahden, the CEO of Shmoop, a humorous yet effective education platform. Follow along as we discuss everything from the entrepreneurial journey to the educational technology sector.
Listen as Andy explains just how valuable former teachers are in the EdTech industry, detailing why they are great candidates from hire. He also reveals the biggest mistake he sees teachers make in interviews, offering great advice to help you avoid making it. Whether you have a specific interest in the educational technology sector or are curious about what other career paths are possible for you, you’re going to want to press play on this one.
Listen to the episode in the podcast player below, or find it on Apple Podcast or Spotify.
Why This CEO Hires Teachers Podcast Recap and BIG Ideas:
✨ Just like there are alternate paths to learn how to teach, there are alternate paths where you can apply your teaching experience.
✨ Former educators are valuable assets to an EdTech company, from sales, customer success, and project management.
✨ Former educators bring an unmatched level of relatability and understanding to the EdTech customer base.
✨ Contrary to popular belief, sales roles in EdTech companies are helping customers realize if/how your products can aid in meeting their specific initiatives and goals, not pushing an aggressive sales metric.
✨ Authentic confidence and a willingness to learn are some of the most desirable qualities of a qualified candidate in an interview.
✨When battling imposter syndrome, remember that there’s no such thing as perfection.
✨ Working in a startup environment often provides more flexibility and diverse opportunities not available with larger, more established companies.
Why This CEO Hires Teachers Podcast Transcript
Andy shares his journey going from mechanical engineer to CEO of the popular EdTech company, Shmoop.
Daphne: Hey, Andy. Thank you so much for joining me here today.
Andy: Thank you for having me really appreciate the time that you take to do these things.
Daphne: So Andy, you are the CEO of a company called Shmoop. Can you tell me a little bit about your entrepreneurial background and, more specifically, discuss the world of educational technology?
Andy: Absolutely. So, I received an education in mechanical engineering and went to work as a mechanical engineer for a short time after I graduated. I noticed how much training I was doing, showing people how to use advanced technology to get their job done. That was my introduction to education and my first role as an educator of sorts, as I showed people how to break down and accomplish complex tasks.
While the topics and skills were highly advanced, many of the same rules apply when it comes to educating anyone. I was teaching baseline reading and writing skills to more advanced technological techniques. As time went on, I became more and more involved with innovation in the 3D design space.
Eventually, I started working for a large software company, Autodesk, which facilitates software to millions of customers. While leading those teams, I realized one of our biggest problems was educating our customers on such a large scale. When you think about educating 35 million people from a digital office, it becomes really challenging. We used to educate all of our customers on how to use our products during in-person training classes. As our customer base continued to grow globally, we started doing training online. It was hard to keep up with training every time the new technology came out, which was about every three months.
So, I found myself starting a business unit at a company called Pluralsight, which, up to that point, invested its time and effort into creating course content to teach coding. I came into the business to add aspects of design and engineering and together we grew the business and were able to make the company public in 2018.
That’s when I was introduced to Dave and Ellen Siminoff, the founders of Shmoop. They started Shmoop wanting to provide resources and help to teachers and to be able to speak a student’s language to democratize education at scale. Since I look over as the CEO of Shmoop in 2018, we’ve continuously been driving innovation. It’s been awesome getting involved in online education and education in general where we can get involved earlier in someone’s development and progress. As I continue my journey forward of running different businesses, it’s been such a pleasure to learn and grow with all of our students.
It’s because of the educators on his team at Shmoop, Andy explains, that the company can continue to grow and succeed.
Daphne: It sounds like you have a lot of experience working in technology companies in general, but this is really your first time in a more traditional K-12 education company. So, from a business perspective, what differences are you seeing when you’re making decisions as a CEO of an education-focused company?
Andy: People ask why I’m involved in K-12 education since I’ve never actually worked in K-12 education, but one of the well-known secrets to successfully operating a business is running a business that you know nothing about. It allows you to approach it with a completely different lens and add a new perspective. But that’s only part of the equation. The other thing any successful CEO understands is the value of a team.
Sure, I might understand how to run, grow, and invest in a successful EdTech organization, but I might not have as clear of an understanding of how we should think about test prep solutions or how our products should be used in the classroom. That is where additional team members come into the picture to make our business successful. The business is only as successful as the people running it, including the entire team.
We’re really beneficial enough to have an awesome team here at Shmoop. We all work to drive success forward and know doing so is reliant on every one of us. So, our team members who understand education and understand how our applications fit into the classroom and help teachers are vital and valuable to our continued growth and success.
Former educators bring an unmatched level of relatability and understanding to the EdTech customer base.
Daphne: I love how you acknowledge that everyone has their zone of genius. You’re very aware of the fact that educational pedagogy might not be yours. That’s why you invite subject matter experts or former teachers onto your team so they can bring their zone of genius to the company. Would you say that’s a strategy you use when hiring?
Andy: While my background is in tech, I do have some knowledge in education after spending years developing video-based course content. I have an underlying understanding of how to teach people. A teacher receives a certification or degree to think about how to teach someone, right? My education and understanding about teaching came from my visits to YouTube or an MIT learning access platform. I was still learning how to break down and deliver content.
So, the concept of behavioral science and how people digest information are things that I’ve learned in a different way than a traditional educator has learned them. That’s where the different lens comes into play. But the concept of bringing it all together and applying it to the classroom and K-12 education relies on how we create products. At Shmoop we do that directly with our customers through interviews. Nothing is ever created based on our perspective of what is relevant, engaging, or needed.
The way that we approach it is honestly the way everybody should do it. We sit down and interview as many customers as possible. I mean, some of the coolest things we’ve developed this last year are all customer ideas. So, you have to understand your customers’ needs and how to communicate with them about their needs.
Once you’ve built products, you have to be able to relate to your customers. I’m not going to resonate as well with our customers as a teacher or former teacher would, right? That’s why all of our sales reps, as an example, are former teachers. We employ former counselors, principals, and superintendents too. The team at Shmoop is made of people with a variety of different backgrounds in the K-12 education space.
When you mix the business and the relational side together, it’s the most beautiful thing ever. It ends up being a powerful way to think about how we develop the technology. A teacher might want to create all these amazing bits of educational content or an amazing educational platform, but they don’t know-how. Truthfully, it’s a massive undertaking with a lot of complexities. Now, when you bring those worlds together, in our opinion, that’s how you develop the most innovative, helpful content that’s going to exist in the classroom.
Sales jobs in EdTech might not be what you think they are.
Daphne: There are so many people who are listening to this right now who aren’t quite comfortable with the idea of customers or a “sales” position. So, let’s strip that back for these types of positions in an EdTech company, like Shmoop. When you’re talking about how your customer success managers or your sales team works with customers, you’re talking about former teachers talking to different districts to figure out how your products can support them in meeting their specific initiatives and goals. It’s not about pushing an aggressive sales metric or a sales quota.
Former teachers understand those initiatives and goals. They know the difference between a gifted and talented focus or a stem focus or a school that might be struggling to bring its readers to a third-grade level. Former teachers have been in those positions and understand the thought process and the customer base’s concerns, especially the district’s teachers.
Andy: Exactly. We all bring different values to the table that are helping our world progress. At some level, some of us get better at doing one thing versus another thing. I can relate to many of your listeners because when I first worked as a mechanical engineer, I quickly realized I didn’t want to be one for the rest of my life. The job didn’t fit my passions and desires. I was concerned because I had gone to school for almost a decade to learn how to do mechanical engineering, and suddenly, I was changing my mind. It ended up being one of the best things for my professional career. You don’t have to be meant for one specific job forever.
When you think about business at the simplest level, you’re really just creating something that fills a need or helps the world progress. Then you’re selling that product to the people who need to use it. In the end, you’re both becoming more successful as a result of doing both of those things. Yes, there is a scientific aspect to creating amazing products, but there’s also a more interpersonal science to actually selling a product. You have to be able to resonate with, connect with, and provide value to others.
I think it’d be hard to work for a company if the products you built didn’t really positively impact the world. So, in a way, these sales roles are really about providing something really meaningful. I would say most of the customer-facing sales reps at Shmoop have awesome relationships where they’re texting their customers and help them through any roadblocks so the students can really reap the benefits of the products.
So when you think about it, you’re not really selling per se. What you’re doing is partnering with your customers to figure out a path forward to drive success. A lot of people are afraid to move into sales, but without products and sales, you don’t have a business. You have to sell products in order to learn, grow, and create more beautiful products.
Our sales reps, customer success managers, product developers, engineers, and UX designers all have educational backgrounds. The other individuals who don’t offer the other perspectives that we need to build the products and run the business.
At the end of the day, you have to bring together a wide spectrum of values different people bring to the table to have a successful business. But those with experience working in the school system, those people are really the only individuals able to resonate and understand the challenges in the classroom and who can communicate how the products we offer provide value in those spaces.
Product Manager Roles are another place for teachers in the EdTech space.
Daphne: I wanted to touch upon different roles that are very common in educational technology companies, like a Product Manager. Truthfully, a lot of teachers hear you say all of these words, and they don’t know what they mean or they immediately feel imposter syndrome, thinking they could never do something like that.
At Shmoop you reach out to your customers, your clients, your school districts, and you ask them what they need to give you some sort of assessment of what improvement to make to your products or what your next products or curriculums could be. Then it would be the job of a product manager to go out and relay that information to the marketing team and determine how to best relate it to and simplify it for teachers.
The marketing team needs to be aware of what type of language to use or avoid because teachers and schools need to understand the products and how they are going to help them. Product managers are oftentimes someone who ties all the pieces together while maintaining a timeline. That could easily be a job for a former teacher at an educational company.
Some of the sales roles at these companies have implementation aspects to them, meaning you’re actually helping the customer learn how to use the product. Any teacher who’s been doing virtual learning at this point is basically an implementation specialist after all of this virtual learning. Yet, they still feel a sense of imposter syndrome when it comes to actually applying for roles like this.
They don’t realize they can. It’s about approaching the conversation with customers with the knowledge of what that company does and how it could support teachers. A lot of teachers lack that confidence.
Learn more about Shmoop and the roles that they prefer to fill with former educators.
Daphne: Okay, so what does Shmoop exactly do? And how does it support teachers? Because there are probably teachers who are listening right now who might want to look it up as well.
Andy: We have over 6 million B2C, direct to customer, users on our platform that come to us for homework help, ideas for working on their essays, and help with their math. We supply all that stuff for free as a way to help those students.
On the back end of our platform or the paid portions of our platform, schools purchase access to Shmoop for additional resources in the classroom.This includes access to over 400 courses geared towards grades 6-12. We also provide video-based learning with over 10,000 videos that can be used in conjunction with their curriculum.
We also offer Heartbeat, which is our social-emotional learning tool. It was created by our teachers for our teachers. Heartbeat works to analyze 55 factors. We worked with Digital Promise, a nonprofit organization, to look at student’s reading or writing skills and how those things may be influenced by, or are connected to, their emotional behavior or other factors. Heartbeat analyzes and provides insight to teachers regarding, for example, how tired or emotional a student is feeling and how much that influences their ability to concentrate on reading and comprehending a paragraph.
We also provide Test Prep content and materials for ACT, SAT, and for 35 AP exams. Last but not least, we provide tools around a response to intervention, which is very relevant in today’s world with how everything with COVID and the effects of teaching kids virtually. All these tools are intended to be used by teachers in the classroom. Schools buy the access to those products and materials.
The roles that we have that help get those products and materials into the classroom range from the development of the technology to actually getting the technology in the classroom. We have sales reps, or as we call them, account executives and senior account executives, Customer Success managers, who are primarily working with the customers, including teachers, principal, and superintendents over the course of their one-year contract. We usually sell license access for 1-3 years.
We also have support specialists. These are people who implement the products and offer support if there’s a problem. Support is an important aspect of our business, which means all those people are dealing with teachers, principals, and superintendents all the time. Therefore, it’s valuable for me to fill that role with someone who has a teaching background. I can teach someone how to sell, support, or implement products, but I can’t teach someone what that classroom experience is like. So for the teachers who have that imposter syndrome, they actually have what we need.
There’s tremendous value in having a former teacher work with our clients. I hope your audience can realize they have that value, and they can progress their career forward in EdTech if that’s something they want to do.
Daphne: So even when you were describing what programs and materials you offer, I started thinking of questions that your average salesperson wouldn’t think to question. They were all questions that teachers would have. And it’s a good indicator that your teacher customers might ask them too. Former teachers would be able to get it and understand the question or concern, rather than someone without an educational background making an inference or comment that could actually hurt the company. EdTech companies are fully aware of that.
Andy: In sales lingo, what you’re referring to is called objection handling. When a customer comes to us with an objection, it’s a sign test that they’re actually interested. So, we like objections. We need people who understand those objections to know if they’re legitimate or if they’re invalid and can be reversed with an explanation.
Objection handling is about listening to and understanding what the customer’s concerns are. In order to listen and understand, you have to come from a breadth of knowledge of what they’re dealing with. And then once you’re able to understand and digest what that individual is saying. But it’s being able to answer those questions and handle objections in a positive way where you are actually answering the questions realistically is really important. Ultimately you’re selling the understanding of what your customer’s needs are and being able to fulfill them– or to move to the next person who wants those solutions.
Insider tips for a successful interview with an education company.
Daphne: I’m sure you’ve had teachers who were great fits for a position not able to translate their teaching experience well in an interview. Can you share some of those experiences where teachers just weren’t able to translate their experience confidently and therefore didn’t land a job with your company?
Andy: We haven’t had 100% success with all teachers, and the biggest issue I see is a lack of confidence. Confidence is one of the biggest hiring challenges, and while it can come through in many different ways, it should always be authentic. If you really believe that you’re capable of doing something, you’re going to be able to either learn, figure it out, and progress forward or not.
For example, no one ever told me what I needed to do to become a CEO of a company. There are no classes for that. So I had to go figure it out. From a teacher’s perspective, you can’t get frustrated when you have to put work and effort into learning something new and ultimately progressing. The people who struggle most are those who would rather remain in the bubble of their comfort zone. Now, a lot of people think that they’re comfortable inside that bubble, but sometimes you have to break out of your comfort zone to know you’re really good at something.
You just need a small success to know it is possible. Our first priority with any teacher we hire at Shmoop is to help them achieve their first win. No matter how big or small, that first win gives them so much confidence that they’re hungry to learn more and continue progressing.
The root of authentic confidence comes from a desire to succeed. And there’s nothing wrong with a desire to succeed and make money. When you make a living for yourself doing something meaningful in life, there’s so much gratification and power there. It’s having that desire for success while realizing you’re going to fall down at times and have to get back up. It’s really a mix of drive, passion, and desire. If you can add confidence to that mix, you’ll get to the finish line.
Daphne: You know, in the Teacher Career Coach Course, I have an entire module just based on interviewing and getting them prepped for all the basic questions of why they left their job in teaching. Honestly, one of the best pieces of advice I have is to remember you are human because there’s also an element of personality and fitting into the company culture, right? You don’t want to go in acting like a robot because it makes it hard for the interviewers to see the value you bring to the role and determine if you’ll embrace the role and are a good fit all around. So, yes, go in with confidence.
It’s also realizing it’s okay to have one or two answers you’re not 100% sure about. It’s okay for you to say, “I’m super confident at the fact that I can learn that,” and give examples of when you’ve stepped up to the plate and learned a new curriculum or new technologies and platforms. Maybe you haven’t studied user experience before and would need to look a few words up at first, but show you’re willing to learn.
I think a lot of teachers fall into the natural genius category of imposter syndrome. If they don’t feel 100% confident in something from the start, they don’t want to try it because failure is a scary possibility. If they’ve already gotten so far in their teaching career, taking a step back and starting from the beginning is scary.
Hey, I fail all the time. Everything I do has imposter syndrome all around it, but I just keep pushing. I just officially Incorporated this business last month, and I feel like I have no idea what I’m doing, but I have the kindest, sweetest team of people underneath me. As far as capitalism goes, I wouldn’t be able to pay them if I didn’t have some sort of revenue coming in from a digital course. And that’s the way that you can keep doing something beautiful.
Andy: I totally agree. We’ve all heard the phrase, “practice makes perfect,” but there is no perfect. You could be the best teacher and still get offended by someone commenting on having a negative experience in your class. We take things personally. Rather than get mad, you have to know you have more ability and room to grow. You have to remember that no one’s perfect.
You’re going to start at the lowest common denominator, and you’re going to progress forward, right? Practice helps you get towards perfection, but you’re never going to accomplish perfection. You can be really good at something, but the goal is to keep getting better. So, you have to be willing to learn and you have to be able to take feedback. It can be challenging at times, but it’s so important.
Daphne: And there’s a learning curve, too. If you are a teacher and transitioning into a role where you want a lot of flexibility, and you want to learn a lot of different parts of a company, I recommend finding a startup company. They can give you those opportunities that a more established business may not be able to. There’s often more room to grow and define your role. They might notice you have a knack for marketing, and they might toss a few marketing projects your way. That’s a more diverse experience to add to your resume. From your experience with building businesses, would you agree?
Andy: Yeah, absolutely. If you’ve ever worked at a startup before, you know that the smartest people in the world are the ones who work at startups. In my experience, I’ve realized the people I was working around were 10-20 times smarter than me. I thought I was going to come into this company being the more knowledgeable individual, and then I realized I had a lot to learn. So, startups have a real benefit in the fact that the most brilliant people are usually working at those entities. I mean, some of the biggest, most progressive companies, like Amazon, still consider themselves a startup because of that.
When you’re working in a startup environment, there is a need to be able to work amongst multiple teams cross-functionally. When we created our product marketing message for Heartbeat, our sales teams had to go together, and our product teams had to come together. Everyone took on marketing responsibilities to make it happen. So yeah, you get the benefit of being able to learn a lot of different facets of the business when you’re working for a startup.
Daphne: I support startups because I’ve come from one myself. I know that people who don’t have prior experience with them, sometimes the label alone, sparks fears of instability or a tech culture that they might not understand. So, I really appreciate you diving into that mental block that might stop teachers from exploring a career path in Edtech.
Thank you so much for taking the time to be here today, Andy. I know there are so many teachers who are listening and want to check out the resources Shmoop has to offer. Especially those created by teachers and counselors for courses and social-emotional learning. Where can they find your products?
Andy: They can find everything they need at shmoop.com. We have two primary locations on Shmoop, one for students and one for teachers. So, go right to the top, go to “teachers, schools, and districts,” and they’ll find all the information that they are probably interested in as far as what we’re providing to schools.
We’re super excited to get Heartbeat, our SEL tool, out to market this summer. We recently hit our 10,000th student interaction. Heartbeat will give teachers insights into their student population that they just wouldn’t have access to otherwise. They could ask questions all day long, and students won’t answer. So, we’re excited to provide those insights to teachers.
And you know, we are hiring right now. We’re hiring sales reps and customer success managers. These positions can all be found on our website under our career section, as well as on LinkedIn.
We’re really excited about where we’re going as we continue to progress in the future and how many more schools and districts across the United States, Canada, Mexico, and across the globe we can help as we continue to grow the business.
We really appreciate you having us on the show. This conversation has been absolutely awesome and very real. I hope it reaches many different teachers and gets them thinking differently about the possibilities in their futures.
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