I’m an accidental tax software business expert. When I joined Avalara (the leading sales tax software company NYSE:AVLR) in 2014, it was a big career pivot. Prior to that, most of my experience was in building marketing products. I love growth, data, and helping people achieve economic self-sufficiency. Obliquely, operationalizing tax created friction and limited growth in every business I was a part of. I felt that I could have a larger impact by removing tax as a growth obstacle than by directly focusing on growth.

“ I love growth, data, and helping people achieve economic self-sufficiency.” - Tela Andrews, Co-Founder & CEO

While at Avalara, I had the opportunity to lead in key areas that helped me form a point of view on what the ideal tax software business would look like. I was the product leader for the flagship sales tax product, AvaTax. This was the first product the business offered when it launched in 2004, when the scale of the market was unproven. Many of the problems I solved were a direct result of a limited early vision at the product level.

Before joining Avalara, I tried to use and buy the product. I failed; You couldn’t buy the product without talking to sales and even then it was challenging to learn to use. My history as a growth PM just wouldn’t allow me to let this lie. I drove the self-service experience at the company, launch the ability to buy and pay for products online, when few believed that anyone would do this. It was a resounding success. We added APIs built on these self-service capabilities to scale distribution, and transformed the trajectory of the business. This experience led me to a central concept that has become the epitome of BearTax’s current focus- accessibility. There had to be a way to empower partners and end-users to navigate this new world of taxes without all of the red tape.

The Road to Accessibility

While buying the product was easier, using the product was still challenging. I was involved in many acquisitions during this time, and more since leaving Avalara as I’ve consulted with other large tax software products. I’ve learned that once a tax software business achieves scale it’s nearly impossible to re-platform and materially improve the experience.

I was limited in how much pain I could solve in tax by the original vision and early decisions of the product. I formed a clear point of view on what an ideal tax software product would be. Then, I filed it away in my mind, since there were no new and interesting tax domains emerging in the way that sales tax emerged with eCommerce. When I left Avalara in 2018, I thought that was my last involvement with a tax product.

BearTax was launched that same year. I admittedly didn’t see the opportunity of crypto tax at that time. In fact, when a friend went to run growth at one of our now-competitors, I remember thinking “you’re building tax software for people who don’t want to pay taxes!”. I was so very, very wrong.

The MVP product that Vamshi and the founding team built was absolutely perfect, in all its’ limitations. When we first started working together, Vamshi apologized for gaps in the product. I told him that was a strategic advantage, and tech debt we didn’t need to pay off. I think he was surprised when I thanked him for not building more. Now he understands.

BearTax was perfectly positioned as a launchpad for the vision that I had formed in my previous efforts. What’s more, the crypto market was very clearly the largest market for a tax software product that the world has ever seen. Solving this problem would unlock the full potential of the web3 economy. It was clear that the potential value proposition would extend far beyond taxes.

The BearTax name has a place in our heart, and a great reputation in the market. But, it’s not the name that takes us to this future vision.

Read about our rebrand here.

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