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When a career change is and isn't the answer


Actuary turned software developer Chris Cherry talks about his Naked journey.

“Choose a job you love and you will never have to work a day in your life.”

We wouldn’t call this bad or good advice. But we are sure that even professional ice cream tasters have days where ice cream is the last thing they feel like eating. In joining Naked, one of our early team members underwent a career change. The lessons he’s learnt along the way resonated with many of us at Team Naked. We want to share his story in the hope that it can connect with more people.

Chris Cherry, one of the original Naked team members, first heard the term ‘actuary’ in his maths class when a friend mentioned that his older brother was one in London and that if Chris enjoyed maths then it might be something to look into.

“I remember shortly after telling my teacher that I was going to be an actuary. He looked at me, rolled his eyes and asked me if I even knew what I was saying,” said Chris. “Only years later did I understand what he meant.”

“I’m not even sure by the time I finished studying that I knew exactly what an actuary did. Throughout the training, you’re learning the basic skills and you get some exposure to the different environments that an actuary might work in typical ones like insurance, pensions, or investments.”

It was only at his first job at a small actuarial consulting firm, Quindiem, that he started turning all the theory he learned into practice. And by all appearances, it was a great first job. Being a small company, Chris got regular exposure to senior members of the company. It was a strong team that always aimed to support one another.

Teamwork was something Chris had learnt to value from his high school cricket days. “Cricket was a very special sport to me – it was a sport where I might not have always performed but I could always count on the others in the team to lift me up,” says Chris. He felt like he could count on the team at Quindiem in the same way, but his teacher’s question still stuck with him.

After a couple years of work and finishing his last board exam he kept asking himself if – 20 or 30 years down the line – he might look back and feel like all he was doing was filling his pockets to make himself comfy, but not really contributing to others or society. It was at that point he decided to change what he was doing.

Chris was seriously considering theology or medicine as alternative careers. But at the same time, one of the senior people at Quindiem, Stephen Jurisich – who was also the head professor of Actuarial Science at Wits University – approached him. Chris had done a few guest lectures in the Actuarial department at Wits, and Jurisich asked him if he wanted to lecture in a more permanent capacity.

“I loved it; it was something new and teaching felt very fulfilling. I got very involved: preparing video lectures as supplemental material (this was before COVID-19), and trying to make sure all the assignments were fun and had good data.”

One thing Chris has been known for since he was a young boy, is that he is always willing to put effort into whatever he is doing. “I haven’t always been a natural at things, but as soon as I decide to do something, I give it everything I’ve got,” he says.

He ended up lecturing for seven years. Towards the end, he still wasn’t sure if being an actuary was what he wanted to do. However, lecturing helped him to see actuaries in a different light. He could see that there were other ways of doing things and that being an actuary was really just about the skill set. It was up to him how he wanted to use those skills. But he still wasn’t sure where he could go without feeling like he was selling his soul.

Not long after, the founders of a new insurtech startup called Naked Insurance came to the university to recruit some students. They explained the Naked Difference and how it helps better align the interests of the company with those of the people they’re insuring. They also said not to think of the company as an insurer, but rather as a tech company that sells insurance. In other words, expect to get your hands dirty with some non-actuarial work.

Chris started at Naked before the company had even sold its first policy. His first big project involved working in the claim submission process: making sure that Naked was taking into account a whole bunch of information that was being submitted at claims stage to help instantly approve certain claims, and potentially pick up any fraudulent behaviour.

This project required some software development work, and he ended up having to learn some of the coding languages like TypeScript and JavaScript. Naked’s CTO, Jade Venter, put him on NodeSchool to learn a few of those languages. But he knew he couldn’t just be learning and doing tutorials full-time: it needed to translate into something useful.

“It became a bit of a juggling act, doing a couple of tutorials in my spare time and on weekends,” says Chris. “I wanted to make sure that I could integrate what I had learnt into the code we were building for the claims submission project.”

A couple years later and Chris says actuarial training has equipped him well to work in an insurance company context and he feels like he has a lot to offer in that area. But for now, his focus remains on gaining a deeper understanding of what it takes to implement new software features while playing a role that can speak to both actuarial science and software development.

“I want to reach a point where I understand what we want as a business and what challenges we face,” he explains. “I feel like I’m in the perfect position to be able to bridge the gap between the developers and the actuarial team, and ensure that everyone understands what they need to do and how it all contributes to the bigger picture.”

Chris believes that many more lessons await him, but is grateful that the ones he’s learnt already have helped get him to a place where he’s excited about the path that he’s on. He’s also grateful to be in a position where he can recognise that quotes like “Choose a job you love and you will never have to work a day in your life,” are often just that – quotes.

“No job is perfect. I revisit this throughout my career,” he says. “I’ve learned to recognise that there are going to be those times where there are some things that you don’t enjoy doing, but you just do them because it’s part of what needs to get done to help contribute,” he says.

“I look back now and realise that my first job at Quindiem was a golden opportunity – I learnt a lot and I worked with great people,” said Chris. “And a mistake I possibly made was running away before I knew enough to make a good decision. Sometimes it’s easy when you’re in a position where you feel like you’re in a bit of a rut – it’s easy to think that if you leave, it will make things right.”

“Someone once told me this: ‘You take yourself with you.’ So if you can’t overcome those issues where you are now, just make sure they’re not going with you to the next place you go to.”


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