What

Pilot is an SF-based startup-focused accounting firm, offering tax, bookkeeping, and CFO services on its platform to more than 1700 customers. Founded in 2016, Pilot has raised more than $160M in venture funding, including a $100M Series C in 2021, with support from Sequoia, Stripe, Whale Rock Capital Management, Bezos Expeditions, and Index Ventures. 

Why 

To Waseem Daher, CEO and Co-Founder of Pilot, what makes the company unique is how it combines its employee-driven services with technology. “When we think about the efficiency or effectiveness of our accountants versus the unaided accountant, our back-of-envelope estimate is something like 4x,” Daher said. “But the reason we do it this way is because the customer wants a trusted partner who knows their business—they do not want more accounting software.” 

Daher said Pilot has been able to operate successfully and serve its customers’ back-office needs because of the suite of technological solutions that have come out over the past decade. The rise of fintechs and APIs—solutions like Gusto and Stripe—have let Pilot commit to automating the back-office operations related to billions of expenses per year.

How

Given the sensitivity of the back-office work, Pilot began with a core set of functions that it helped automate and then scaled its product from there. “We would rather do a small number of things super well and knock them out of the park,” Daher said. It began with bookkeeping services, and then expanded into tax and fractional CFO offerings when sufficient client demand made an expansion into those areas clear and justifiable.

Pilot has three primary stakeholders that shape its product roadmap. A key demographic is internal: its in-house accountants and tax experts who use Pilot’s product to do their work. The company has placed its accounting and engineering teams next to each other to facilitate product feedback and accelerate cross-pollination between the teams.

The other two personas depend upon a company’s size. Smaller outfits—two founders in a garage, for example—may hand over their back-office demands to Pilot, but lack financial knowledge and do not want to be involved in the day-to-day operations of their back office. The second persona, when a company is further along, is a dedicated point person, like a VP of Finance, who functions as a one-person finance team. That persona tends to be “quite sophisticated and have specific views about what they want and how they want it done,” Daher said. Pilot views those demands positively, as it means the company has to meet those expert standards consistently. The company tweaks its engagement with customers according to these personas, balancing transparency with customer expertise.

Daher sees Pilot as the AWS of companies’ infrastructure: automating and running areas that are not the high-leverage areas of a company’s expertise or operations, such as finance, legal, accounting, HR, recruiting, IT, and real estate. “It's actually wild that every company has to reinvent this stuff from scratch… that by definition is not being done scalability,” he said. While that’s the long-term vision, Pilot will continue serving its core set of customers—startups, e-commerce businesses, and professional services companies—and begin to expand its client base and mix over the next year.