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Here’s why I went from being an educator to leading one of Asia’s top tech start-ups


I’ve been an educator for almost all my working life. From teaching financial literacy to schoolkids, to mentoring university students alongside some of the world’s most influential companies, my passion has always been building relationships and helping people grow. That hasn’t changed since I joined Carousell, one of Asia’s most successful start-ups, as their Country Lead for Australia. In fact, it’s the main reason why I signed up.

I’ve always told my mentees that the people you work for, matter far more than the brand. When Carousell told me that this new role was open, I’d known its co-founders Marcus and some of its employees for more than a year through Austern International, the education start-up I co-founded. Carousell had given several batches of our students a great experience of start-up life during their stays in Singapore, and I’d seen first-hand the love and drive that their entire team brought to growing the business. I also knew my direct manager-to-be, JJ, from his time at Airbnb and jumped at the opportunity to be mentored by someone whose perspective and skills are immensely different to mine.

Carousell isn’t as big in Australia yet, but in Asia it’s gotten so famous that people have started using it as a verb! The online marketplace lets anyone list pre-loved items for sale, but unlike some other platforms it takes its “Peer-to-Peer” label quite literally. Face-to-face meets are the norm, and hundreds of thriving communities of people with similar interests have sprung up on the site. When you buy something, you know you’re dealing with a real person. Your purchases matter.

The turning point

That experience upended how I thought about the things I buy and value. I’ve loved fashion ever since I was a kid: I ran a fashion blog as a student and always enjoyed shopping for clothes, but never thought about the lasting impact of what I purchased. The first time I tried Carousell, I bought a beautiful blue dress at an obscenely low price. Low enough that I messaged the seller asking why she was selling the dress – and a whole stack of other designer clothes – for so little.

Her answer? She’d recently become a single mother, and needed the money to support her child during this rough patch. I couldn’t look at my spending the same after that.

I’ve been at Carousell for just over a month now. I’m still part of Austern, mentoring our students and guiding the business where it’s needed, but I’m fortunate that the business is sustainable at this point without my day-to-day input. That’s given me the chance to throw myself in the deep and be the “new kid” again – ready to learn and grow.

Carousell Office

The journey so far

Transitioning from education to tech hasn’t been without its challenges. At Carousell, the Australia team works mostly through collaboration software like Slack, rather than the face-to-face meets, forcing me to articulate myself far more clearly online – something I’m not especially used to! The new role also, unsurprisingly, involves far more meetings with my different teams and international counterparts than Austern’s once-a-week tempo. And analysing huge amounts of data, every day, isn’t something any teacher typically has to do.

Sometimes you do wonder, “What am I doing here?” In my first meeting with the other country GMs, I barely understood half the terms they were using. I had a choice: to pretend to have it all together like they did, or ask the stupid questions. You can guess which one I chose! I’m doing my best to follow the advice I give to Austern’s students: disrupt yourself before trying to disrupt an industry, treat failure as an opportunity, and above all never be too afraid (or close-minded) to say YES to something new. You might just discover your next passion – like I’ve done.

Some people might say that technology rules today’s world – but it’s the other way around. Platforms like Carousell are growing so fast because we value relationships and people more than ever, both amongst our team – we were voted Singapore’s best tech start-up to work for just this month – and our user community. When I talk to our buyers and sellers, they tell me they keep coming back because they share our vision and they want their purchases to benefit a real person…and because of the relationships they’ve built through the site.

As a teacher by training and an entrepreneur by calling, I know my strength has always been in relationships – the sort of genuine, durable ones that go beyond business or work. Those sorts of relationships can take you to all sorts of strange and unusual places, like supporting a single mother’s new life or joining a tech start-up with almost no tech experience. You can’t succeed just by knowing technology – you’ve also got to understand humanity.

Jamie Lee is the new Australia Country Lead of Carousell – one of Asia’s fastest-growing tech start-ups and top workplaces.

Jamie Lee

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