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  • Tim Kane

The Philosophy of Chasing Whales

It is a well-known fact that most companies in Canada would be considered SMBs – a staggering 98% of businesses are small to medium-sized.

I always ask myself – if the footprint is so big, why do they seem to be the forgotten ones when it comes to innovation in employee benefits?

I have my own theories on this, but every large Venture Capital funded company we encounter always has the same narrative – they cannot afford to facilitate small businesses. If the market is so big, then why is it forgotten? In reality it is not, but most companies coming into the market focussing on SMB business have either left the space completely or quickly refocused on large companies.

The manpower required to launch and support the groups, whether it is 2 people or 100,0000 people, is the same – the larger groups are just more lucrative. I will go out on a limb here and say in our industry being small employee benefits, especially in the SMB market, is not a Venture Capital Model. The simple reason is that it is too slow, and the market is not understood enough to understand that once you land a whale, your investors won’t be happy to go back to landing fish.

The myHSA platform was built to facilitate small and medium-sized businesses with the computers doing the work – making it scalable. While this may seem like a crazy concept, it is foreign in the tech industry. When bootstrapping, you only have one model and, if you’re lucky, one pivot—in our case, a system rebuild—but you have to be careful with this. Without a giant pot of investors’ money supporting you, you may quickly realize why doing it right the first time may be your only option.

This is especially true when building technology – it is expensive to build and even more so to rebuild. Most technology companies build an MVP and then use humans to do the back-end work on what the system is supposed to do. The idea is to grow and prove the model using humans, and eventually, the system will catch up. A favourite example of mine demonstrating this is the Steve Jobs movie, when he launched the Macintosh—trying to get the Macintosh to speak, but had an issue doing so. The scene ends with success, the Macintosh speaks, but it was not what it seemed—it was a human speaking with the audience believing it was the computer.

As first-time tech founders and a bootstrapped company where every dollar mattered, our system had to be efficient, so there it was. The business was not built by flying across the country and buying steak dinners for anyone that would listen—it was built to be lean, profitable, and scalable.

For myHSA, it takes the same effort to launch a 3-person account as it does to launch a 1,000-person group. However, one thing is for certain, it will be an amazing experience—making our model perfect for the SMB market.

So, how are we doing and has our philosophy changed? A few months back, we hit the milestone of having 100,000 employees on the system. Our joke for the celebration was everyone here gets two scoops of teriyaki sauce on their favourite dish from the Japanese QSR restaurant, Edo.

We know how to celebrate our wins, but we are more designed to celebrate what we have built – the perfect mix of human customer service and technology efficiency.

Tim Kane

CEO & Founder



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