The AI Assistant That Actually Gets Work Done | Jean-Denis Greze, Town

Jean-Denis Greze, former CTO of Plaid and engineering leader at Dropbox, explores the evolution of Town, an AI-powered personal assistant designed to manage email, calendars, and professional workflows. Initially launched as a tax-focused tool, the company pivoted to a broader agent-based model after identifying a critical need for AI that filters information and automates routine tasks without requiring users to master complex technical prompts. Success in this space relies on domain-specific pre-processing and a system-oriented design approach rather than merely chasing the latest LLM updates. While current AI narratives often overstate immediate productivity gains, the long-term potential for these agents to act as genuine colleagues—reducing cognitive load and filtering noise—remains a transformative goal. The discussion highlights the challenges of founder-led sales and the necessity of maintaining a clear product vision amidst a rapidly shifting technological landscape.