"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech E46: Ex-Plaid CTO on Why Tax is the Ultimate AI Challenge, with Jean-Denis Greze
May 21, 2025
Jean-Denis Greze, Co-founder and CEO of Town and former CTO of Plaid, dives into the challenges of tax preparation for small businesses. He discusses the innovative use of AI to automate processes while still emphasizing the role of human expertise. The conversation explores the startup's origin, unique opportunities in the small business sector, and the evolving landscape of tax technology. Jean-Denis also shares insights on market dynamics and the transformative potential of AI, revealing why he believes tax is the ultimate AI challenge.
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Origin Story of Town
- Jean-Denis Greze was motivated to start Town after hearing from SMBs and software platforms about the pain in business tax prep.
- AI enabled him to prototype automation that could handle varied, nonstandard tax documents, making the idea viable.
Pick Pain, Tech, Market
- Look for pain points combined with technological shifts and large markets when choosing startup ideas.
- The tax space was overlooked by others, making it a rich opportunity for innovation and less competition.
AI Unlocks Tax Prep Automation
- Business tax prep lacked innovation because inputs are complex and no standard formats existed before AI.
- AI and LLMs can now automate tax returns from messy, unstructured documents, unlocking scalability not possible before.