Health Tech: Jennifer Chou Of EntryLevel On How Their Technology Can Make An Important Impact On Our Overall Wellness

An Interview With David Leichner

David Leichner, CMO at Cybellum
Authority Magazine
11 min readNov 2, 2022

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Don’t deprive the world of what you can do just because you don’t believe you’re “supposed” to do it. Just try and see what happens!

In recent years, Big Tech has gotten a bad rep. But of course many tech companies are doing important work making monumental positive changes to society, health, and the environment. To highlight these, we started a new interview series about “Technology Making An Important Positive Social Impact”. We are interviewing leaders of tech companies who are creating or have created a tech product that is helping to make a positive change in people’s lives or the environment. As a part of this series, I had the pleasure of interviewing Jennifer Chou from EntryLevel.

Jennifer Chou graduated with a Psychology degree from Simon Fraser University, where she interned in the Health & Counselling department. Now working in Growth at EntryLevel, Jennifer helps improve the well-being of others by helping them find fulfilling careers in tech.

Thank you so much for joining us in this interview series. Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your childhood backstory and how you grew up?

I was born in Taiwan, but moved to Vancouver, Canada when I was 3 years old. I was a very creative child who loved knitting, origami, and other arts and crafts, but there was always an expectation that “arts” wouldn’t pay well — at least not as well as being a doctor or lawyer. Fortunately, those expectations were never really forced on me, and I found a passion in psychology because I loved learning about how people worked and how to help others. I was also a very shy child because English is my second language and I am also hard of hearing. Interacting with other students was a struggle in elementary school.

However, by the time I got to university, I grew out of my shell and became very involved on campus — hosting events, being a mentor, and more. I was very involved in student politics and held an executive position in the Disability and Neurodiversity group, where we advocated for the well-being of marginalized students.

My friends and I also saw how our peers were struggling to find jobs, and it was terrible for their well-being because they needed money for tuition and work experience for their future careers. We founded a startup to help students with arts backgrounds like me find jobs in tech, like UX Design and Web Development. Although I eventually left that startup, I used my experiences there to inform my work at EntryLevel, which also helps people reskill into fulfilling careers.

Can you share the most interesting story that happened to you since you began your career?

When I look back on my career, I was always very lucky — it felt like opportunities were given to me rather than me having to go out and search for them. However, I’ve realized that it’s because I set up the conditions for those opportunities to happen.

For example, I found my passion in the edtech space primarily because someone asked me for help solving an education-related problem: people weren’t getting the necessary skills training they needed to transition to a job in tech.

Because that person asked me for help, we built a startup tackling this very problem. I always thought it was very lucky that they came to me for help, but I’ve realized they only approached me because no one else was willing to put in the work with them. They heard about me because I had a track record of being a responsible leader (through organizations and projects I’ve worked hard on), so they reached out to me because of my experience.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

“A leader isn’t someone who orders others around. It’s someone others look up to as a good example.”

I’ll always remember my mentor telling me that in my first year of university. It’s how I was able to pursue so many opportunities and become a mentor to others.

For example, he once asked me if I’d like to participate in a panel discussion to give my advice to other students. I had never done public speaking before, but with his encouragement, I successfully participated in the panel and went on to speak in many other events.

Now, with EntryLevel, I host monthly events where I help our students learn skills to land a more fulfilling career.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Dedication takes a lifetime, but dreams only last for a night.”

This quote reminds me to keep persisting and work for something I want, even in the face of failure.

For example, there were some difficult times in my life when I worked on my own startup. I was really busy and had poor work-life balance, so my mental health was struggling. However, I persisted, and although I eventually had to leave that startup, it was an experience that helped me get to where I am today. The opportunities that I had were due to my experiences with that startup.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

1. Reliability

As I mentioned before, I never saw myself as a leader. However, people kept encouraging me and giving me opportunities in leadership positions, which ultimately led me to where I am today.

This is because I was always very reliable — whatever work needed to get done, I would show up on time and do everything with dedication. This led people to trust me to handle more difficult tasks, which is how I got a lot of experience that helped me figure out what I loved to do.

2. Kindness

I feel like this isn’t mentioned as often in business circles, but helping others really helped me in my career.

Being helpful and genuinely caring about others led to so many cool opportunities I wouldn’t have had otherwise. People would refer me to so many projects I ended up enjoying a lot. Seeing the people I’ve helped succeed also made me feel more fulfilled and acted as more fuel to the fires of my passion (sorry for being cliche). That’s why I never get tired of what I do — I’m always reinvigorated when I see how many people I help.

3. Resourcefulness

If I don’t know how to do something, I’ll find out how.

Instead of letting it stop me and saying “I can’t do it,” my mindset is “I’ll learn quickly and try it out.” That’s part of the reason why people see me as a leader — even if I don’t know something, I’ll figure it out eventually.

That’s also why I love working in startups. Things are always changing so you’re always learning something new — and quickly. I’ve learned more in 3 months working at a startup than years working for a larger company.

Ok super. Let’s now shift to the main part of our discussion about the tech tools that you are helping to create that can make a positive impact on our wellness. To begin, which particular problems are you aiming to solve?

At EntryLevel, we’re helping people reskill into tech careers they love. I’ve talked to a lot of students who’ve taken our online courses, and a lot of them:

  • Are unhappy at their current jobs — whether it’s a toxic workplace or they’re bored with their work.
  • Want a happier, more fulfilled life by working in a purposeful career.

Part of the reason I love helping others find fulfilling careers at EntryLevel is because I would’ve loved this resource a few years ago, when I was in the same position. I wasn’t happy with where I was in my career and it was straining my mental health and relationships with others. Taking online courses to transition to tech wasn’t very helpful — I needed to work on projects, not just watch videos.

After taking an EntryLevel course (the only online course I finished due to the unique cohort-based structure and commitment bond model), I walked out with a cool project which I immediately applied to my work life. Eventually, I found a career (at EntryLevel) that I look forward to working at every day.

How do you think your technology can address this?

EntryLevel provides training to help people reskill into a more fulfilling career in tech. What’s unique about our courses is that we run on a 6-week cohort-based structure. It’s flexible and done on your own time, but there are still deadlines to meet. Modules are unlocked every few days and you get to interact with peers on Discord (although there are no group projects).

At the end, if you complete the portfolio submission and peer review before the deadline, you’ll get a refund. 90%+ of our students mentioned that this commitment bond model (where you get a refund upon course completion) motivated them to complete their projects, which they then used to get jobs in the field.

We’ve had multiple success stories from our students who landed internships in their desired fields: https://www.entrylevel.net/interviews

Can you tell us the backstory about what inspired you to originally feel passionate about this cause?

“Fall in love with the problem, not your solution.”

That’s the advice every founder hears. When I was a founder, I became passionate about the problem many of my peers had: they were unable to find careers they loved because they lacked the experience needed. School taught them theory-heavy concepts, so they never learned how to apply what they learned. It’s even more difficult for career transitioners.

I wanted to find a way to help them find fulfilling careers like I have.

So I started an edtech startup with my friend, and eventually left that startup and worked for another edtech startup (EntryLevel). Even if the “solution” (startup) changed, the core problem was the same.

How do you think this might change the world?

Education will be more accessible to everyone, rather than just people who can afford to go to university.

Right now, online courses and skills training are either free (MOOCs like Coursera), or thousands of dollars (live cohort-based courses).

EntryLevel is the in-between: we provide students with a refund if they complete the course, which not only motivates them to achieve their goals, but also makes it more affordable for everyone.

Keeping “Black Mirror” and the “Law of Unintended Consequences” in mind, can you see any potential drawbacks about this technology that people should think more deeply about?

I can’t think of any drawbacks.

Here is the main question for our discussion. Based on your experience and success, can you please share “Five things you need to know to successfully create technology that can make a positive social impact”?

1. Always keep the user in mind.

Often in business, you’ll be asked to prioritize profit and growth. But the best, most successful businesses address their users’ needs and solve their problems.

Example: Duolingo is a leader in the edtech space because they make learning fun without being addictive. Other apps may use deceptive UX patterns to get you to stay on the app for as long as possible, but Duolingo doesn’t do this.

2. Breaks are necessary

Even though you might be passionate about what you’re doing, remember to take care of yourself too. As the saying goes, “you can’t pour from an empty cup.”

In the past, I’ve worked to the point of burnout for social impact non-profits and startups. Even though I really believed in the causes I was supporting, my mental health was declining and I felt stressed all the time.

Luckily, one of the non-profits had a mandatory break time where everyone had to take 2 weeks off. After the 2 weeks, I felt a lot better and was able to put my best foot forward again. Without this mandatory break, I would’ve thought I just had to “work harder” for better results…instead, the break was necessary so I could do better work as I felt more reinvigorated.

3. Test many things

The key word here is “test.” In the past, I’ve made mistakes where I went all in on a solution or product and built it, only to realize it wasn’t what people needed.

Just because people say they “would” try your product doesn’t mean they “will” try your product. Conduct a bunch of tests and let the data guide your future directions.

4. Build an effective support system

No one can change the world alone.

Create a support system — whether it’s loved ones, a great team, or just an automated process — to make life easier for you.

I’ve always had trouble delegating. Once I learned to ask for help, my team and I were able to make progress so much faster, so we could deliver our solution to help users earlier than expected.

5. You’re not too young, too old, too inexperienced, etc. for this

A lot of people (myself included) don’t pursue something — not because of a lack of passion, but because they don’t think they can do it.

For example, I was still a university student when I worked at my first startup. I thought I was too young and inexperienced, and almost didn’t pursue it.

But with the encouragement of my friends, I ended up learning so much and helping some students from my school.

Don’t deprive the world of what you can do just because you don’t believe you’re “supposed” to do it. Just try and see what happens!

If you could tell other young people one thing about why they should consider making a positive impact on our environment or society, like you, what would you tell them?

The main reason is that it’s fun!

I’ve worked in places where I didn’t find purpose. I felt bored and unfulfilled, and would dread going to work every day.

But since finding a career helping others, I’ve never felt dread when it’s time to go to work. In fact, sometimes I struggle to NOT work weekends because I love what I do so much. Every time an EntryLevel student shares a success story with me, I can’t help but feel grateful that I was able to be part of their career journey.

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them. :-)

Nzinga Young, or @veganzinga on Instagram. This isn’t super education-related, but I’ve been a follower of hers for ages and love all her content. Discussing veganism, real estate, environmental activism, etc. with her would be a dream come true!

How can our readers further follow your work online?

I do Growth for EntryLevel, so most of the things I post on https://www.entrylevel.net/ social media consists of my learnings!

Thank you so much for joining us. This was very inspirational, and we wish you continued success in your important work.

Thank you for this opportunity.

About The Interviewer: David Leichner is a veteran of the Israeli high-tech industry with significant experience in the areas of cyber and security, enterprise software and communications. At Cybellum, a leading provider of Product Security Lifecycle Management, David is responsible for creating and executing the marketing strategy and managing the global marketing team that forms the foundation for Cybellum’s product and market penetration. Prior to Cybellum, David was CMO at SQream and VP Sales and Marketing at endpoint protection vendor, Cynet. David is a member of the Board of Trustees of the Jerusalem Technology College. He holds a BA in Information Systems Management and an MBA in International Business from the City University of New York.

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David Leichner, CMO at Cybellum
Authority Magazine

David Leichner is a veteran of the high-tech industry with significant experience in the areas of cyber and security, enterprise software and communications