Scaling smarter: How AI is transforming accounting firms

‍From Math to Finance to Founding Puzzle

Sasha didn’t start in accounting—he started in math.

“I love accounting. I'm not an accountant. I'm not an accountant by training. I did an arguably sexier degree. It's called mathematics.” 

But math is everywhere, and in his case, it led straight to finance. After working at Citigroup and launching multiple fintech companies, he kept running into the same problem: small businesses didn’t have access to the same level of financial insight as large enterprises. 

At big companies, CFOs and finance teams drive strategy. They have the data, models, and expertise to make smart decisions. Smaller businesses? They’re stuck waiting until month-end for reports that may or may not tell them what they need to know. Sasha saw an opportunity to change that.

Why Accounting Needed an AI-Native Overhaul

For years, accountants have relied on tools like QuickBooks and Xero. But these systems weren’t built for automation—they were built for manual data entry.

 “AI is going to make mistakes. AI will always make mistakes. Humans always make mistakes.  If you're building something to be AI native, meaning you don't want AI to hallucinate, you could add all this extra context so that you can make it work really well for computers to do it.” 

With Puzzle, the goal wasn’t just to automate bookkeeping. It was to create a system that could surface real financial intelligence—without accountants having to dig through spreadsheets.

“Accountants are the facts of a business. It's the truth of a business, whether you like it or not. But what if we could help you deliver in less than the time it takes to just generate normal cash books?”

Accountants Aren’t Going Anywhere—They’re Becoming More Valuable

There’s a lot of fear around AI taking jobs, and accounting is no exception. But Sasha doesn’t see automation replacing accountants. He sees it giving them more leverage.

“There might be some segment of the market who just truly doesn't care about their financial health. But the overwhelming majority of people don't want some AI software generating something that has all this personal liability associated, I don't see that as a thing.”  

The real shift isn’t about replacing accountants—it’s about moving them up the value chain. Instead of spending hours cleaning up transactions, firms can focus on advisory work, helping businesses understand what their numbers actually mean.

The Future of Accounting Firms

By 2030, Sasha believes the best bookkeeping and accounting firms won’t just be keeping records. They’ll be strategic partners.

“You're going to be their partner. You're not going to be their vendor or their outsourced firm. You're going to feel like part of their team that is helping them make their business better.” 

That shift is already happening. As AI handles more of the rote work, firms that embrace automation will have a choice: take on more clients or work fewer hours while delivering the same value.

Why Transparency Builds Trust in AI

A lot of companies promise perfect AI-powered accounting. Sasha doesn’t buy it.

“I’ve seen  a couple venture back startups in the space say ‘Our AI is a hundred percent.’ Nothing is a hundred percent.” 

Instead, Puzzle is built to be transparent. Every transformation is tracked. Every entry is explained. If something goes wrong, firms can trace exactly where it happened and fix it fast.

“The importance of accounting is provable accuracy, whether it's AI or not. You want to have confidence in numbers, because if you're making business decisions based upon garbage in, you're going to get garbage out.”

The Bottom Line

Accounting is changing. AI isn’t replacing accountants—it’s giving them superpowers. Firms that embrace it now will be the ones leading the industry in the next decade.

Want to hear more? Listen to my full conversation with Sasha Orloff on After the First Million.

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