Pilot Raises $100 Million After New Funding Round

The startup now has a valuation of $1.2 billion, and the funding round was led by Jeff Bezos.


Expedition, a venture capital firm headed by Jeff Bezos, has led a $100 million funding round for Pilot. The funding round was co-led by Bezos and Whale Rock Capital, with Silicon Valley investors, Index Ventures, and Sequoia also participating in the funding.

Pilot enables smaller businesses to outsource their administrative tasks such as taxes and payroll. These outsourced tasks saw a considerable increase in demand over the past year during the COVID-19 pandemic.

Waseem Daher, Pilot’s CEO, and co-founder said: “People want to do this virtually. They don’t want to have to go down to Main Street with their box of receipts and visit their accountant’s office.”

Sixteen years ago, Daher had interned at Amazon before he started two other companies. One of those companies was purchased by Oracle, while Dropbox bought the other one.

Pilot is based in San Francisco, and it closed the latest funding round last week, nearly doubling its valuation to $1.2 billion. Previous investors have been Stripe founders John and Patrick Collison and Diane Greene, former CEO of VMware. Daher referred to a solution that Amazon Web Services might provide when comparing the two companies and said that Amazon’s services allowed developers to focus on building their business instead of figuring out how to host a website.

“There’s all of this annoying, tedious, scary, and important back-office stuff that you need to do as a small business owner. Owners should focus on running a company at scale, and Pilot should be doing the back office stuff for you.”

Pilot has employed several former accountants as its employees, and they work directly with a small business to complete its administrative tasks, including bookkeeping, payroll, bills, and taxes.

Thus far, Pilot has partnered with American Express, Stripe, Bill.com, and Gusto. While Daher says Pilot is “tech-enabled,” it doesn’t call itself a software company. Pilot makes its revenue through subscription fees.

Its revenue almost doubled during the coronavirus pandemic, even though small businesses suffered the most among enterprises during the shutdowns. Pilot’s revenue has nearly tripled each year since its 2017 founding.

Daher hinted that his company is growing because owners of businesses are becoming more aware of automation, and since more are working from home, it’s an appealing option. Millennials are also more open to outsourcing their work, and they also happen to be the group starting smaller businesses today.

Pilot is also Daher’s third venture with co-founders Jeff Arnold and Jessica McKellar. The trio met at MIT when they were undergraduates in the computer lab.


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