Digital CPA by CPA.com Disrupting Tax: From Paper Trails to AI Agents
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Jun 23, 2025 
Leroy Kerry, CEO and co-founder of Filed, shares his journey from building fintechs in Europe to revolutionizing tax automation in small-town America. He discusses how agentic AI can streamline tax workflows, addressing inefficiencies and reducing manual effort. Leroy tackles the importance of security and transparency in AI adoption and the vital need for firms to modernize or risk losing talent. The conversation also explores the evolving role of AI in tax preparation and its potential impact on future advisory services.
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Hands-On Learning in Tax Firms
- Leroy Kerry interned at tax firms to understand their workflow and challenges firsthand.
- He discovered outdated processes like fax machines and paper documents still in use today.
AI Automates Drudgery in Tax
- Much tax work involves repetitive, manual tasks and data entry that no one enjoys.
- This drudgery is exactly what AI is well suited to automate and improve.
Agentic AI Transforms Tax Workflows
- AI agent technology can perform specialized tax tasks and communicate between agents to handle complex workflows.
- Unlike rule-based tech, agents can reason, search, and dynamically handle diverse tax compliance work.