Career advice from the man who founded Outsurance and now runs Rain Mobile

When Rain announced in October 2017 that Outsurance founder and CEO Willem Roos would lead its mobile business, it took the market by surprise.

The insurance industry is very different from mobile telecoms, and to take on established operators will not be easy.

However, when Rain Mobile chairman Michael Jordaan revealed that Roos was a shareholder in Rain from the beginning, it made more sense.

Roos wants the challenge of disrupting the telecommunications industry, and the fact that Rain Mobile was based in the Western Cape was a big bonus.

He took the reins at Rain Mobile in December 2017, and is now preparing for a commercial launch of the service in 2018.

Willem Roos Interview

MyBroadband asked Roos about his path to the top, what advice he can share, and what Internet connection he uses at home.

What was your first job and how much did it pay?

My first job was being a junior lecturer in Actuarial Mathematics at the University of Pretoria. I honestly cannot recall the exact salary, but it was not much.

How did you end up in the telecoms field?

I invested in Rain two years ago and joined the board. I became fascinated by the industry and opportunity to again be involved in a startup of a business.

Did you get a big break which propelled your career?

I was very fortunate to have met my cofounders of Outsurance at a very young age. But success came later with lots of hard work.

What is the best and worst aspects of being CEO?

Problems obviously drift upwards, and so a CEO spends a significant portion of time dealing with issues. What I like most is experiencing success in business with a great team of people, and seeing the positive impact the business has on the people involved and broader society.

Do you have any plans after you step down as CEO?

I just started as CEO of Rain so not thinking that far ahead at all.

What career advice do you have for a young person?

Read widely and try and understand the world around you. It easier to be innovative if you have broad knowledge, together with being an expert in your own field. Innovative people succeed.

Be entrepreneurial early on in your career. This does not always mean that you need to start a new business on your own. Do something new and innovative in your current job. If the culture of your current employer does not allow that, resign and find a company that will.

Tech and business choices


Which smartphone do you use?

iPhone X.

Which laptop do you use?

Macbook Pro.

What is the best gadget you have ever bought?

Garmin Fenix Smartwatch.

What is the worst gadget you have ever bought?

Apple Watch.

What Internet connection (fixed broadband) do you have at home?

Fibre, with Rain LTE as backup.

What is the best investment you have ever made?

Outsurance and Rain shares.

What is the worst investment you have ever made?

Selling some Outsurance shares.

What is the best business book you have ever read?

Good to Great by Jim Collins.

Now read: The inside story of Rain Mobile’s new CEO

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Career advice from the man who founded Outsurance and now runs Rain Mobile