What is the history of software-enabled bookkeeping services, what has been successful, and what opportunities exist for the future?

We've been trying to—for lack of a better word—‘automate’ bookkeeping since the dawn of JavaScript. So many companies have come and gone trying it. On some high level, it does seem to make sense: Accounting is a set of rules, right? If software is good at following rules, we should just be able to automate all that.

As we went along, we learned that software is not just a set of rules, it's a set of guidelines. It's not just a set of numbers; it requires business context. I think that's why this holy grail of fully automated bookkeeping hasn't been realized yet. 

In many respects, that's okay. I don't believe we can fully remove human out of the loop. It's just a question of how we can use the technologies we have to remove more and more of the manual, tedious tasks—to the point where, instead of one bookkeeper handling five, 10, or whatever number of clients, one bookkeeper can do 50, or one controller can do 100. They're just really coming in and just looking at a couple things.

The dawn of JavaScript and automating repetitive tasks came first, and there were many things that it couldn't handle. But then we started having APIs for everything, open APIs, we can just go in and grab the data that we need, and that's where Bench and Pilot were really coming up. Now, the exciting thing is we're at a new inflection point with AI and the technologies that GPT-3 brings to us, so I think there's a lot more tasks that are being automated going forward.