Photo Credit: Pilot
Pilot, a leading provider of bookkeeping services for small businesses, recently announced it raised $40 million in Series B funding led by Index Ventures. Stripe and several existing investors participated in this round as well. The company also recently announced Pilot Tax — which will help customers with end-to-end business needs. Including this round, Pilot has raised $59 million.
Founded in 2017 by CEO Waseem Daher, COO Jeff Arnold, and CTO Jessica McKellar, Pilot is helping bring bookkeeping into the digital era. To help small businesses with advanced bookkeeping needs, Pilot sets them up with dedicated full-time account managers in the U.S. who can quickly learn the ins-and-outs of their business. And Pilot integrates automatically with the financial services customers already use. Using a blend of custom software and expert bookkeepers, Pilot is able to deliver accurate bookkeeping that frees up time for entrepreneurs so that they can focus on growing their business.
“We founded Pilot because we saw first-hand from entrepreneurs struggling with this area that it was time to bring bookkeeping into the 21st century,” said Daher. “We are proud that our customers find our service to be trustworthy, accurate, reliable, and delightful to use, and that investors like Index and Stripe are excited by our vision.”
With this round of funding, Pilot is going to accelerate the adoption of its bookkeeping service and fuel product development. Currently Pilot is handling the bookkeeping for more than $100 million per month in financial transactions.
“Bookkeeping is a problem that should be solved with technology and represents a massive new category of software,” added Index Ventures partner Mark Goldberg. “Startups and small businesses deserve a smarter solution for their back office so that they can focus their creative and entrepreneurial efforts on building what they love, and not managing their books. Pilot is making this possible, and we’re thrilled to double down on this exciting company.”
The Pilot Tax platform service supports 1099 filings, income tax filings, and tax support. And the combination of bookkeeping and tax services means that Pilot can offer a full scope of services and create a more seamless experience for customers.
“It’s so nice to have everything in one place. Before Pilot Tax it felt like I was managing a million different tools to get our books, tax filings, and 1099s all handled,” explained Gem co-founder and CEO Steven Bartel. “Now I can just trust Pilot to cover everything.”
Daher, Arnold, and McKellar met 15 years ago while working as members of MIT’s student computing group. And Pilot is the third startup that they launched together. The first startup was Ksplice — which built technology that could update software systems without requiring a reboot — and got acquired by Oracle in 2011. Then they launched a group chat tool for businesses called Zulip and was acquired by Dropbox in 2014.
