Meet the Newest Fintech Unicorn: Bezos Expeditions & Whale Rock join Pilot’s Push to Modernize the Back Office

Additional investment doubles Pilot’s valuation to $1.2Bn and increases Series C to $100M raised as Pilot rapidly scales “big-company superpowers” for SMBs

SAN FRANCISCO–(BUSINESS WIRE)–#Accounting–Pilot, the largest provider of back office services for startups and small businesses in the U.S., announced today that it has closed on additional funding led by Bezos Expeditions (the personal investment company of Jeff Bezos) and Whale Rock Capital, with participation from Sequoia Capital and Index Ventures, that increases the Series C to $100 million and doubles the company’s valuation to $1.2Bn. The additional funding enables Pilot to further expand its breadth of back office services that offload day-to-day distractions and allow small business owners and founders to focus on growth.

“Since the earliest days of my career, including an internship at Amazon in 2005, I’ve been inspired by Jeff’s relentless focus on delivering an exceptional customer experience. We’ve brought that same DNA to Pilot’s customer-centric approach: over 80% of our business is driven by customer referrals and organic interest,” said Waseem Daher, Founder & CEO.

“Pilot is revolutionizing the back office by combining white-glove customer service with carefully-engineered software,” said Kristov Paulus, Partner at Whale Rock. “We look forward to supporting Pilot in their vision to make back office services as easy-to-use, scalable, and ubiquitous as AWS has with the cloud.”

In 2020, Pilot completed more than $3 billion in bookkeeping transactions for its customers, which range from pre-revenue startups to established companies generating more than $30M of revenue a year. It has also established co-marketing partnerships with other industry leaders including American Express,, Brex, Carta, Gusto, Rippling, Stripe, SVB, and Techstars.

Pilot continues to see strong momentum on its mission to bring big-company finance superpowers to SMBs. With Pilot, founders, business owners and finance teams are able to:

  • Maximize financial outcomes and growth. For SMBs without a full-stack finance team, Pilot CFO Services fills the void and builds financial strategies and plans that accelerate growth, increase cash flow, and improve profitability. “It has been incredible working with Pilot CFO Services to uplevel our financial models and analysis. I have been waiting years for a service like this!” Dave Shields, CFO at Bolt
  • Track and control spending. Comparable to work done by senior controllers at large enterprises, Pilot provides monthly variance analysis for all its bookkeeping customers, ultimately empowering SMBs to make better budgeting and spending decisions. “I really love Pilot’s monthly variance insights. This is something I used to do manually every month and it was incredibly tedious, so it’s nice to get it ready-made without having to lift a finger,” said Daghan Altas, VP Operations, r2c.
  • Access small business tax credits. Many companies miss out on special federal and state tax credits available specifically to small businesses, including an R&D tax credit that can exceed $250,000 in savings. “I really appreciate the work Pilot did for us. A short call with their team let us save $86k in tax credits we wouldn’t have otherwise known to claim.” Nancy Nugent, Operations Manager, Pathrise

Started by three-time co-founders Waseem Daher, Jeff Arnold, and Jessica McKellar, Pilot was created to solve problems they’d faced themselves while building their two previous companies.

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. The company provides small businesses with dedicated finance experts—which Pilot hires as full-time, U.S.-based employees—who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping that gives entrepreneurs the freedom to focus on their business, as well as an array of additional financial services.

Pilot was founded by Waseem Daher, CEO; Jeff Arnold, COO; and Jessica McKellar, CTO. It is their third startup, after two successful exits. Pilot has over 1,000 customers and has raised over $150 million to date. Investors include Sequoia Capital, Index Ventures, Stripe, Whale Rock, and many world-class entrepreneurs, including Jeff Bezos, Patrick and John Collison, Drew Houston, Diane Greene, Frederic Kerrest, Hans Robertson, Adam D’Angelo, Paul English, Howard Lerman, Joshua Reeves and Tien Tzuo.

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Lisa Tarter

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