Why AI-Native Accounting Is the Future with Sasha Orloff

Accounting is no longer just about balancing books. It’s about delivering insight, enabling smarter decisions, and driving the strategic direction of a business.

Sasha Orloff, CEO and Co-Founder of Puzzle, believes the future of accounting is AI-native. With years of experience in fintech and scaling financial operations, Sasha recognized the opportunity to transform accounting—not by sidelining professionals, but by empowering them. Puzzle was built on the idea that AI should be integrated into the foundation of bookkeeping, enhancing accuracy, increasing efficiency, and elevating the role of accountants into trusted advisors.

In this episode, Sasha explores what it really means to be AI-native, why transparency and trust must be at the core of automation, and how firms can shift from task execution to strategic impact. If you're in accounting and want to understand where the industry is headed, this episode offers a clear view of what’s next.

What you’ll learn in this episode:

• Why being AI-native goes far beyond adding AI features to outdated systems
• How traceability can build trust in automated processes
• What it takes to grow your firm without overloading your team
• Why AI should support better decisions—not just faster ones

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