How AI is reshaping accounting with Sasha Orloff

Accounting is no longer just about tracking numbers. It’s about delivering real financial insights, making better decisions, and shaping the future of businesses.

For Sasha Orloff, CEO and Co-Founder of Puzzle, that future is AI-native. After years of working in fintech and scaling financial services, he saw firsthand how accounting could be transformed—not by replacing accountants, but by elevating their role. By integrating AI at the core of bookkeeping, Puzzle is redefining how firms approach accuracy, efficiency, and advisory work.

In this episode, Sasha breaks down what it truly means to be AI-native, why trust and traceability matter more than ever, and how accounting firms can shift from manual work to high-value strategy. If you’re in the accounting world and wondering how AI will shape your future, this conversation is a must-listen.

In this episode, you’ll learn:

• The difference between AI-native and AI add-ons: Why layering AI on top of legacy systems isn’t enough
• Why traceability is key to AI adoption: How accountants can maintain accuracy and confidence in automation
• How accounting firms can scale without burnout: Why AI should free up time for strategy, not just speed up processes

Jump into the conversation:

(00:00) Meet Sasha Orloff

(02:06) Sasha Orloff’s unexpected path to loving accounting

(05:07) Bringing big-company financial insights to small businesses

(07:15) Why AI is transforming accounting in 2025 and beyond

(09:23) AI isn’t replacing accountants—it’s making them more valuable

(12:00) AI-native vs. AI add-ons: What’s the real difference?

(16:13) AI mistakes are inevitable—why traceability is the solution

(19:30) The risks of using too many disconnected tools

(22:15) Why AI will never be 100% accurate—and that’s okay

(26:20) The biggest mistake firms make when adopting AI solutions

(31:36) Why QuickBooks’ incentives don’t align with accounting firms

(38:00) Scaling bookkeeping revenue without adding more work hours

(45:00) What the AI-powered accounting firm of 2030 looks like

(50:00) How to automate without losing control of accounting decisions

(53:32) Why accountants must lead AI adoption—not fear it

(55:28) Matt’s takeaways