Beyond Feature Requests: AI, Discovery and Strategic Product Thinking

​Beyond Feature Requests: AI, Discovery and Strategic Product Thinking with Holly Hester Reilly.

​AI is changing how product teams work — but are we using it to uncover real customer insight, or just automate confirmation bias at scale? In this session, product leader and former Shutterstock discovery lead Holly Hester-Reilly explores why the best PMs in the AI era won’t be the ones processing the most data, but the ones asking better questions.

​Through practical examples and hard-won lessons, she’ll show how to use AI to uncover unmet customer outcomes, hidden constraints, and 10x product opportunities — while keeping human discovery at the center of great product work.

​About Holly

​Holly has spent nearly two decades helping product teams build the right things, not simply build faster.

​As Group Product Manager for Datadog’s Data Platform organization, she leads a team supporting 500+ engineers, applying evidence-based strategy and continuous discovery at scale.

​She founded Product Science Group in 2017, creating training, frameworks, coaching, and a podcast focused on better product discovery. Her experience includes scaling Shutterstock Editor to 5 million users, helping Ergatta reach a successful exit, and growing PSG to $880K in revenue.

​She also teaches product management and AI at NYU Stern and believes deep customer understanding is essential in the AI era.

​Meeting Agenda

• ​Welcome and intro to PLX (5 min)

• ​Speaker’s talk, including Q&A (45 min)

• ​Participant feed back survey (5 min)

• ​Networking breakouts (15 min)