E46: Ex-Plaid CTO on Why Tax is the Ultimate AI Challenge, with Jean-Denis Greze

In this episode, Sasha Orloff talks with Jean-Denis Greze, Co-founder and CEO of Town, about building an AI-powered tax solution for SMBs, exploring the startup’s origin, the balance between automation and human expertise, strategic market targeting, funding insights, and the transformative potential of AI in tax preparation. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠https://notion.com/startups/puzzle⁠⁠ Puzzle 📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠https://puzzle.io/⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/jeandenisgreze/ https://town.com/ -- X/SOCIAL: @jgreze (Jean) @TownTaxCo (Town) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:48) Intro (01:20) Jean-Denis Greze: The origin story of Town (02:10) Challenges and opportunities in business tax prep (03:41) Role of AI in automating tax preparation (05:50) Market dynamics and constraints in tax services (15:49) Sponsors: Notion | Puzzle (17:14) Unique needs of small businesses (24:38) Future of AI in tax preparation (26:12) Segmenting the small business market (27:15) Building trust and scaling AI (37:14) Exploring AI agents and their potential (47:21) Fundraising and future plans (50:57) Wrap