Pilot - Bookkeeping Management
Founded in 2016, Pilot has scaled to become a Unicorn by offering a virtual platform that manages bookkeeping, tax and CFO services for businesses.
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Founded in 2016, California-headquartered Pilot provides financial back-office services like bookkeeping, controller, and CFO to small businesses. It does this by integrating advanced custom software with financial experts. SMEs are provided these services by financial experts who use advanced custom software to ensure accuracy and consistency.
In 2021, the company became a unicorn after raising $100M in a Series C funding round led by Jeff Bezos’s venture capital firm Bezos Expeditions and hedge fund Whale Rock Capital, with participation from Sequoia and Index Ventures. The company is now valued at $1.2B.
Pilot is backed by notable investors like Sequoia, Index Ventures, Bezos Expeditions, Whale Rock Capital, and Stripe.
Business Overview & Products
Pilot operates across the US and provides the following financial products to businesses:
How It Works
Pilot provides financial back-office services to small businesses and startups by combining intelligent software with world-class accountants. It mostly employs former accountants who are assigned to work directly with small businesses for administrative tasks such as bills, bookkeeping, payroll, and taxes. These employees interact with companies to collect their data, use internal tech tools to organize it, and then structure it to produce a set of accurate books.
Upon signing up with Pilot, businesses are appointed financial experts to manage their books with the help of advanced software. This software automates detailed, error-prone manual tasks making it easier for experts to analyze them and make decisions accordingly. Initially, the expert will interview business owners to learn everything about their company, its operations, objectives, and special issues that one needs to be mindful of for accurate bookkeeping. The collected information is used to build a unique checklist for closing the company’s book which is easily accessible in their systems and always up to date.
Each month, the business’s books are checked through a rigorous 14-step checklist, which includes both manual tasks by Pilot’s team members and automated tasks by their software. The first level of checks is done on completed books by Reviewbot software which flags anything that looks questionable so that experts can easily analyze it. After the monthly check is complete, the company receives an email of their books, along with notes from the finance expert.
Business Model & Pricing
Pilot has a B2B business model where it caters to businesses by providing them with bookkeeping, CFO, and tax services. The company earns money through its annual subscription model that is scaled according to a business’s expense rate and needs like institutions, bills, and invoices. It also charges an onboarding fee for the first month of bookkeeping to ensure that the setup process is smooth.
In 2020, Pilot earned $10.5M revenue, served 1000 customers, and had a revenue rate of $20M. That year the company booked more than $3B in bookkeeping transactions for its customers. The company claims its revenue has approximately tripled every year since its inception, except for 2020, when it only doubled due to the brunt of the coronavirus pandemic.
Waseem Daher: CEO and Co-Founder at Pilot. Waseem, an MIT graduate, previously co-founded Zulip, a group collaboration tool for businesses and Ksplice, an open-source extension of the Linux kernel He also worked as Group Product Manager at Dropbox and as Senior Director at Oracle.
Jessica McKellar: CTO and Co-Founder at Pilot. Jessica, an MIT graduate has worked as an Engineering Manager at Oracle and as Director of Engineering at Dropbox. She also co-founded Zulip, a group collaboration tool for businesses.
Jeff Arnold: COO and Co-Founder at Pilot. Jeff, an MIT graduate, worked as Head of Operations at OpenAl and as Head of Products, Clients, and Platforms at Dropbox. She also co-founded Zulip, a group collaboration tool for businesses.
History & Evolution
In 2016, Pilot was launched by Waseem Daher, Jessica McKellar and Jeff Arnold to provide an easy tech solution to SMEs struggling with back-office operations.
In 2019, the company expanded to Nashville with an expectation to create 450 new local jobs.
In 2020, it launched 3 new products – R&D Tax Credit, CFO Services and Extended Services – to become a one-stop trusted provider of financial services.
In 2021, Pilot became a unicorn after raising $100M in a Series C funding round.
According to a study conducted by BlueWeave Consulting, the United States fintech market is expected to grow at a CAGR of 10.1% during 2021-2027.
Businesses in the fintech industry of the United States received $59.8B investments in 2019 from Mergers & Acquisitions, Private Equity deals, and Venture Capital, totaling 1,144.
Suggested Next Reads
Building the Best Bookkeeping Service - Pilot's Founding Story (Waseem Daher, Pilot)
Pilot on the AI-driven 'financial back office' (Poornima Apte, VentureBeat, Aug ‘21)
How Pilot charted a course of not raising too much money (Mary Ann Azevedo, TechCrunch, April ‘21)
Pilot: A Smarter Back Office for Every Startup and SMB | by Sequoia (Sequoia, Jan ‘21)