Digital CPA by CPA.com Disrupting Tax: From paper trails to AI agents
In this episode of the Digital CPA Podcast, host Kalil Merhib sit down with Leroy Kerry, CEO and co-founder of Filed, an AI-powered tax automation company that's redefining how CPA firms approach compliance work. This conversation is part of a series featuring startups from the AICPA and CPA.com Startup Accelerator.
Leroy shares his journey from building unicorn fintechs in Europe to landing in small-town America—where the inefficiencies of traditional tax preparation sparked his mission to innovate. Filed’s technology leverages agentic AI to streamline tax workflows, reduce manual effort, and unlock capacity for firms facing staffing constraints. From automating checklist creation to preparing review-ready returns, Filed transforms the entire lifecycle of tax work—without requiring firms to overhaul their existing tech stacks.
The episode also tackles:
-
The role of agent-based AI versus traditional generative AI.
-
Security, transparency, and skepticism around AI in accounting.
-
The talent risk of not modernizing your practice.
-
Lessons from legal tech transformation.
-
The future of advisory, compliance, and tax planning.
If you're wondering how AI is reshaping tax, what’s automatable versus what still needs a CPA’s judgment, or how to pilot these tools in your firm—this episode is a must-listen.
Additional Resources:
AI skeptic report - https://www.filed.com/report/sign-up-ai-skeptic-to-ai-ready
https://www.linkedin.com/in/leroykerry/
2025 AI in Accounting Report https://www.cpa.com/reports/2025-ai-accounting-report
www.CPA.com🔊 Subscribe to the Digital CPA Podcast for more conversations on the future of the accounting profession!