The Joy of Booking

Pilot Blog

Introducing Pilot

Rebooting bookkeeping for the modern business

Every company in the world needs to maintain its books—a set of financial records that describe how money moves into and out of a company. Maintaining these records today continues to be a labor-intensive process that’s highly inefficient, error-prone, and unpleasant. Pilot is our solution to this problem. We’re a bookkeeping company, and we take care of your books from start to finish so that you can focus on running your business.

Getting your books done today is painful

Whenever you start a company of any kind—whether it’s a tech startup, a doctor’s office, a graphic design firm, a coffee shop, or a construction company—there are two categories of work you spend your time on: 1) the principal reason you started the business in the first place, and 2) all the administrative tasks that you have to take care of to have a functioning business.

In an ideal world, 100% of your time is spent on the first category—you didn’t start your company because you were passionate about the nuances of double-entry bookkeeping or setting up email servers. Fortunately, many high-quality solutions have emerged for lots of these administrative tasks. With services like G Suite, Stripe, Gusto, GitHub, AWS, etc., things that were previously tedious multi-week projects are now doable with a click of a button.

But bookkeeping hasn’t seen any of this improvement. Your options are largely unchanged from what they were in the early 1990s: either you do it yourself (not recommended because you can waste a bunch of your time while producing books of questionable quality), or you hire a bookkeeper and email them PDFs and CSVs. They then do a bunch of clicking around and manual data entry to bring your books up to date every month.

If you check their work, you’re basically guaranteed to find mistakes you need to correct (they’re only human). But what’s even more frustrating is that your corrections are forgotten in a few months because there’s no good way for your bookkeeper to ensure that you don’t need to repeat yourself. In short, even when you find a good bookkeeper, your experience is tedious, slow, expensive, and underwhelming.

The stakes are high, too: your books ultimately (1) form the basis for your tax filings, and (2) help you understand the health of your business, so you’d love to feel confident in their quality. It isn’t a small-scale problem, either: literally every single business out there has this exact challenge.

Introducing Pilot, a bookkeeping service for modern businesses

We started Pilot to solve the problem of bookkeeping—a problem that was the source of a lot of pain for us when running our two previous startups.

Our observation was that the data you need to do your books (from your bank, payroll, credit card, expense reporting tool, etc.) is already in electronic form, and structured with dates, amounts, and memos. In fact, the vast majority of the work is of the form “apply rule X to data Y”—and yet, the current best solution for this problem is “Hire a person, hope all the rules fit in their head, and make them do a lot of clicking.” It seemed obvious to us that software should be doing the heavy lifting, not people.

But the last thing we wanted as startup founders was more bookkeeping software—what we actually wanted was not to worry about bookkeeping at all.

That’s where Pilot comes in. Pilot is a bookkeeping service. When you work with Pilot, you’re paired with an expert bookkeeper in our San Francisco office, and every month, they take care of updating your books for you. Importantly, they have powerful software we’ve developed at their disposal, doing all the tedious, mechanical portions of the process, so that you know they’ve been done correctly.

This two-tiered approach (people and software, each doing what they do best) is what allows Pilot to be far more reliable, accurate, and efficient than any other bookkeeper out there today. When you have a question, you want to talk to a knowledgeable person, not a chatbot. But when you need to categorize 10,000 transactions in a consistent way every month, you definitely need software if you care about it being correct.

Finally, the fact that we’re doing your bookkeeping using software means that we can take care of many tasks automatically: rather than having to ask you to send us reports from your credit card processor, our software can simply download them on its own. Said another way, we can use software to build a user experience that’s actually easy for you (rather than just being convenient for the bookkeeper).

Let’s get started!

We’re excited to share two company milestones with you today:

  1. General availability of the Pilot service. We’ve been in beta for the past year, doing the bookkeeping for 150+ companies including OpenAI, Bannerman, Scale, and /dev/color, among many others. We’ve honed the customer experience and are eager to take bookkeeping off your plate. (You can learn more here.)

  2. We’ve just raised a $15M Series A financing led by Index Ventures. The company’s investors include a long-list of world-class entrepreneurs, including Stripe’s Patrick and John Collison, Dropbox’s Drew Houston, Google Cloud’s Diane Greene, Frederic Kerrest, Hans Robertson, Adam D’Angelo, Paul English, Howard Lerman, Joshua Reeves, Tien Tzuo, and many other folks that it’s a privilege to have involved.

We started Pilot because it’s exactly what we wish had existed for our previous companies. If you’re ready to let us worry about your bookkeeping so that you can focus on running your business, please check us out.

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