Bookkeeping Startup Pilot Lands $40M From Stripe, Index Ventures

Affirm Raises $300M In Series F Funding Round

Bookkeeping startup Pilot announced it has closed on a $40 million Series B round led by Index Ventures with participation from Stripe. The round values Pilot at $355 million.

In addition, the company also announced the public launch of Pilot Tax, its new corporate tax preparation service.

“When you work with us, you’re paired with your dedicated account manager. They’re a full-time U.S.-based employee who works out of our offices and learns the ins-and-outs of your business in intimate detail. Your account manager has a secret weapon: powerful software we’ve built to let us handle the mechanical aspects of your bookkeeping with incredible accuracy and reliability. We keep everything up-to-date in QuickBooks Online, which means you’re on the industry-standard platform as well,” the company wrote in a press release.

Launched in 2017, Pilot’s founders, Waseem Daher, Jeff Arnold and Jessica McKellar, had already created Linux upgrade software Ksplice, which was sold to Oracle  in 2011, as well as Zulip, which was snapped up by Dropbox before it was released to the public.

Pilot handles bookkeeping for more than $100 million per month in financial transactions. It plans to use this latest round of funding to boost customer adoption.

“While dry on the surface, the opportunity is enormous given that an estimated $60 billion is spent on bookkeeping and accounting in the U.S. alone. It’s a service industry that can finally be automated with technology and this is the perfect team to take this on — third-time founders with a perfect combo of financial acumen and engineering,” Index’s Mark Goldberg said to reporters in an email.

And as Daher said, there are no plans to sell Pilot at this time.

“The opportunity for Pilot is so large and so substantive, I think it would be a mistake for this to be anything other than a large and enduring public company,” he said. “This is the company that we’re going to do this with.”



On Tuesday, March 31, 2020 at 9:00 AM (ET) join PYMNTS CEO Karen Webster and panelists Vincent Kilcoyne and Roland Brandli of SmartStream for an in-depth discussion on the need to use transformative digital strategies to remain relevant in today’s challenging financial landscape. The discussion will cover strategies that will allow clients to improve operational control, reduce costs, build new revenue streams, mitigate risk and comply accurately with regulation.