Pilot raises $15M to bring bookkeeping into the modern era – TechCrunch

The first time Waseem Daher, Jessica McKellar, and Jeff Arnold worked together on a startup, they built one that allowed administrators to patch security updates to a system without having to restart it.

So it might come as a bit of a surprise that the next big technical challenge the three MIT graduates want to tackle is bookkeeping . But after selling Ksplice to Oracle back in 2011, it was actually the financial software they had built internally that made the jaws of the finance teams at Oracle drop, Daher said. They had created a continuously-updating internal version of QuickBooks, keeping a close eye on their spending and accounting and not having do hire a bookkeeper to do so, out of pure frustration with the process. And today that’s basically launching as Pilot, a startup that has now raised $15 million in a financing round led by Index Ventures.

“If you look at the history of bookkeeping, it goes back to the 1400s,” Daher said. “Probably the oldest written records were of transactions. Around 1400s, we invented double-entry bookkeeping, a system for how money moves into and out of various accounts of companies. That system, as articulated in 1400 in Venice, is basically still what people do in every American business today. You hire a bookkeeper or bookkeeping firm, you send them all your stuff and they track and produce the set of books. The way it’s done today is the same way it’s done in the 90s, the 40s.”

When a company starts working with Pilot, the actual core experience on the customer side doesn’t really change all that much: they still work with a human on the other end. But the bookkeeper from Pilot is working with the internal tools they have built to bring in the data from the company, organize it and structure it, and produce a set of books that are more accurate than someone might have produced than just doing it by hand. Customers will get the kinds of questions you might expect from a normal bookkeeper as they look to clarify what’s happening, but in the end the process happens much more seamlessly. They can integrate directly with their existing services like Expensify or Gusto (or ask Pilot to help out with that) and then go from there.

That kind of human-software mix is something that’s increasingly common in services businesses — like Pilot — as the tech industry figures out what should be automated and what should still be handled by a person. There are still a lot of things that a person can catch, but there’s also the actual human relationship, which isn’t a kind of repetitive task you’d want to automate with an algorithm. To begin, Pilot isn’t trying to force companies to completely rip out their bookkeeping software and start from scratch, and instead start to collect the electronic information they already have.

“Uber’s like that, the drivers are humans but the software makes them much more effective,” Index Ventures’ Mike Volpi said. “You can see it in a lot of applications where in IT support there’s a few businesses like this, you troubleshoot using software, and when you can’t you fix it pass it to humans. In customer service chats, a lot of times it’s an AI, and when the questions get tricky enough it rolls over to humans. It’s interesting because there are tasks which humans are fundamentally needed and there are tasks that are mundane that software can do and the human can avoid doing. It’s an interesting thesis around this hybrid.”

Prior to Pilot, the team sold another company to Dropbox called Zulip, and spent some time at the company as it continued to scale up (Dropbox is now in the process of going public). Some of the challenge alone was somehow assembling a team that found some fascination with the intersection of accounting, machine learning and working directly with customers, but so far McKellar said that they’ve been able to put one together thus far. And, more importantly, now that they are starting to roll out their service they can start getting some perspective on the industry as a whole.

“I think people can get motivated by almost any problem if you know you’re tackling a big problem for many people,” McKellar said. “But there’s quite a lot of subtlety to what we’re building. The rules and principles of bookkeeping are well define but the real world is really messy, and designing the right systems to automate bookkeeping at scale is actually a tricky thing. We have an incredible engineering team that is able to tackle this with the right mindset it. The analogy you can draw is self-driving cars — that’s a system normally done by a human, everyone understands what it takes to drive a car, what actions you should take. It’s difficult for people to put into words, what are the rules given a set of inputs, but it needs to work and be reliable.”

As more and more of this information comes in, and more and more companies start to work with Pilot, they can start spotting trends in the industry. For example, if a 17th SaaS business with a similar business model to other Pilot companies signs up, they could down the line take a look at their info and spot potential discrepancies based on anonymized trend data picked up from other comparables in the industry — or do a better job of spotting inefficiencies or others. And there are some obvious funnels for this already, like getting the right information for tax purposes to accountants.

There’s going to be a lot of increasing activity in this space, though. Already you’re seeing some funded projects like botkeeper, which are looking to find some ways to automate a bookkeeping service. There’s nothing quite so formalized and an obvious tool that looks to take out QuickBooks (and, again, a lot of these seem to be playing nice for now), and there’s always the chance that Intuit could try to take on the space itself. But at the end of the day, Volpi says it’s based on the team that they’ve assembled — and that combination of humans and algorithms — that gives them a shot at succeeding.

“If you look at a fundamental level, the bookkeeping for the doctor’s office or florist, it is really all following the same underlying principles,” McKellar said. “One of the engineering challenges is to build the tooling and systems and software in a way that’s intelligent. It has to be a set of processes that can flexibly accommodate every vertical over time. In some sense this company, why we raised this, was to validate a huge hypothesis — it’s possible to automate bookkeeping at scale across a range of industries.”

Here’s the rest of the investors in this round, since it’s a long list: Patrick and John Collison, Drew Houston, Diane Greene, Frederic Kerrest, Hans Robertson, Adam D’Angelo, Paul English, Howard Lerman, Joshua Reeves, Tien Tzuo, as well as many others.

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