These serial entrepreneurs sold startups to Oracle and Dropbox. Pilot's CEO explains why their latest effort, backed by Stripe, is the most innovative idea yet.

• Pilot co-founders Waseem Daher, Jeff Arnold and Jessica McKellar are serial entrepreneurs with a gift for spotting and developing disruptive ideas into valuable startups.
• But the trio, who sold their previous two startups to Oracle and Dropbox, believe they are onto their most innovative idea yet: revolutionizing back-end office solutions, beginning with bookkeeping.
• This week, the three-year-old company announced three new products that build on its bookeeping software, to offer tax credit solutions, monthly reports and budgeting services, and a host of smaller services.
• Index Ventures partner and Pilot board member Mark Goldberg called Pilot's vision the "best entry point I've seen in years"
• Visit Business Insider's homepage for more stories.

Waseem Daher, Jeff Arnold and Jessica McKellar seem to have a magic touch when it comes to founding startups.

The trio, who met back at the computer club in MIT, are serial entrepreneurs. They've founded and sold their two previous startups to Oracle and Dropbox. And now they're hoping a bid to revolutionize bookkeeping will grow into a startup that can disrupt the entire fintech market.

Their latest startup Pilot was founded out of necessity, according to CEO Waseem Daher. "We felt the pain [of bookkeeping] very viscerally in our former startup," Daher said, laughing. "Everyone has that problem."

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This, in turn, has led Daher and his cofounders to believe there is a much larger opportunity at play; an opportunity so large that the trio is willing to see the company through for at least the next decade: back-office solutions.

Daher told Business Insider that the trio eventually envisions the company as a one-stop shop for all operational solutions, allowing its customers to focus on innovating their own products rather than deal with the headaches of running business operations.

"The market size and the opportunity lend itself extremely well to building a large, enduring, iconic public company," Daher said.

Pushing into the broader market

After almost three years of perfecting its bookkeeping solution, Pilot is now ready to make its push into the broader back-office solutions market. This week, Pilot announced the release of three new products to compliment its current products.

The company now offers its service for tax credit claims, budgeting and financial analytics, and a host of smaller services like generating invoices, paying supply vendors, and creating monthly reports.

Index Ventures partner Mark Goldberg called Pilot's bid to grow from bookeeping the "best entry point I've seen in years in venture," thanks to its ability to gain greater and greater shares of the back-office solutions market. The startup has raised close to $59 million in funding, from investors including Index Ventures and payments company Stripe.

"One of the fun things about this company is that bookkeeping is a gatekeeper to the rest of the back-office," Goldberg explained. "If you could develop a relationship with a customer, that could probably work for other things as well."

And Goldberg says that Pilot has done exactly that, through investing in its customers. Pilot's customer-facing financial experts are the "secret sauce" to why the business has been so successful, Goldberg told Business Insider. "It's putting a human wrapper around a technology solution," he added.

A guiding philosophy: solving the problem, not delivering the product

Goldberg touched on one of the more unusual features of the Pilot business model. It is a software company that doesn't sell software products to its customers. In the interest of strengthening its customer experience, clients are matched with members of Pilot's team.

That's because the business is all about problem-solving for the client, CEO Waseem Daher told Business Insider. "If you talk to business owners, no one has ever said 'I need to buy more accounting software," he said. "We're going to solve the problem for you, which requires an end-to-end solution."

And that end-to-end solution means customers are connected with Pilot's financial experts, who use Pilot's software to handle bookkeeping - and now its new back-office financial offerings.

"That white-glove, concierge approach is critical," Daher told Business Insider. "That's what lets you sleep at night."

The approach seems to be working for Pilot so far. Since its launch in 2017, the company said it now handles the bookkeeping for approximately $200 million a month in financial transactions.