Bookkeeping, tax and outsourced CFO services company
"We're talking full accrual basis bookkeeping," said co-founder and CEO Jessica McKellar in an interview. "That is: transaction import, reconciliation, categorization all according to your preferences, revenue recognition, payroll, asset capitalization and depreciation, the production and maintenance of all supporting schedules that tie out our proof of work on the balance sheet, the construction of the financial reports themselves—your core financial statements—plus other useful extended reporting like on your recurring vendors."
She added that there is "definitely a bunch of AI and agentic work" but also "just good old-fashioned software that is getting all the pieces stitched together and flowing autonomously."
Asked just how autonomous the AI is, she said that if there is a judgment call that could have a real material impact, it will signal that it needs a human response before moving on, as only humans can make accountable decisions. But otherwise, she said, the normal course of business bookkeeping is usually done without any need for humans. It can even onboard new businesses and configure accounting systems.
"It's like: agent, go onboard this customer. And then it does it. And then, in an hour, it's completing the monthly close. And it's doing that all by itself," she said.
She talked about a customer who needed to do two and a half years of bookkeeping, and needed it done in a month, as the deadline for a grant application was coming due. She told the customer not to worry. She connected the agent to the client's data and financial institutions, then left to do other things at work. When she came back just a few hours later, the agent had completed the entire job.
"It did everything right. And I said, 'Here you go, client. Congratulations. You can go apply for your grant," she said.
To avoid the black box effect, every transaction and decision is logged, providing transaction-level visibility and a full audit history for businesses to review or adjust as needed.
The AI is trained on not just bookkeeping generally, but the specific style and manner of bookkeeping drawn from Pilot's many years of experience using human professionals to deliver the same kind of services. McKellar said there is a particular way they do things, such as paying a lot of attention to "keeping the bank feed, the credit card feeds clean and booking clearing activity through clearing accounts," adding that the solution is customizable to any kind of bookkeeping style.
Like many AI-driven solutions today, Pilot also provides a 24/7 Pilot AI chat-based advisor for real-time, actionable guidance and insights into key business drivers and trends, such as month-over-month spend changes.
While the product is touted as an AI accountant, the degree to which it could serve as a wholesale replacement for a human professional was less clear. The answer to the question depends on what a business owner wants from a human accountant.
"If you're a business owner, what are you trying to get from a relationship with a bookkeeper or accountant? For some business owners, the answer is they don't want anything," said McKellar. "They want basic compliance-oriented financials to file their tax return. They want it to be as low lift for them as possible. They want to be cheap as possible. In that case, if an agent produces correct books quickly, [they can say], 'Ship it. That sounds great.'"
However, she noted that business owners are usually looking for more from their accountants today, namely someone who can understand their goals and help achieve them, and this is something that AI, for now, cannot replace, not even Pilot's.
"A lot of business owners, what they want is to have a person who they know and like and trust, who is in their corner, who is there. You're together in person or on a call and coming up with a strategy for the year and talking about how you're going to execute on that strategy together. A really cheap business owner likely won't hire their own accountant, but most business owners want a relationship," she said.
That relationship is not really something she wants to have replaced anyway, as local accountants play a vital role in the business landscape that goes beyond just accurate financial reports.
"We think it is super important to invest in local accountants who are such important connective tissue in their local business community. And so we want them to be equipped with these incredible things, and bookkeeping is so fun when you can just tell an agent to do all the annoying stuff. We want local accounting firms to benefit from this," she said, adding that they won't be as burdened by repetitive manual work and will be better able to pursue higher value engagements.
Further, she said, even professional accountants find bookkeeping to be a pain, and most would rather not be bogged down in bank reconciliations and revenue recognition anyway. In this respect, the only ones in trouble, she felt, were people who weren't very good at bookkeeping in the first place.
"With full love and respect to humans—I'm a human, I love us—bookkeeping is hard. It's hard to do consistently with infinite patience. … What will not survive is bad books and bad client experience. And you know what? That's OK. I think business owners deserve better, so we should all rise to the occasion given what this technology is enabling us to do," said McKellar.
While Pilot, as a company, also does tax and outsourced CFO services, for now its AI accountant will focus mainly on bookkeeping, as it presents different automation challenges and is even more relationship-based. McKellar doesn't expect that to change soon. While her company may look into those areas in the future, for now it's focusing on this one area.
"Bookkeeping keeps us pretty busy," said McKellar. "We have plenty to do for automated bookkeeping."
