Why Bolting ChatGPT to a Dropdown Isn’t Enough: Repositioning Products in the Age of AI-Native Expectations

​As AI-native products raise the bar for what “intelligent software” looks like, many teams are left wondering: how do we truly evolve - not just bolt ChatGPT onto a legacy UI?

​In this candid, off-the-record session, Dropbox’s former product leader, Vasanth Krishna shares hard-won lessons from helping a large-scale product go from “AI-enhanced” to “AI-first.” We’ll explore what it takes to make AI a foundational shift—not a surface integration.

​Who Should Attend:

• ​Founders and product leaders at mid-to-growth stage SaaS and AI startups.

• ​Those seeking product-market fit in the AI-native era.

• ​Companies on the $1–5M ARR journey.

• ​Leaders navigating post-2023 AI expectations from users, investors, and competitors.

• ​Teams addressing technical debt, UX legacy, or organizational inertia.

• ​Anyone exploring how to retrofit vs. rebuild, differentiate, and build moats.

​What We’ll Cover:

• ​Building AI at the core vs. layering it on

• ​Retrofitting vs. reimagining: how to choose

• ​Lessons from Dropbox’s AI journey — wins, misses, and close calls

• ​Navigating org and infra challenges in AI transitions

​Expect war stories, no-BS opinions, and frameworks you can take home and apply - delivered in a room where you can ask real questions.