Ellen Brandenburger – Product leader and coach; former head of product at Chegg Skills and Stack Overflow’s data licensing team.

How Ellen joined Stack Overflow just two weeks before ChatGPT launched, reshaping the company’s future overnight
The creation of Overflow AI: a team tasked with exploring “what’s just now possible” for developers
Four iterations of conversational search:
V1: a chat UI on top of keyword search
V2: semantic search to handle natural questions
V3: fallback to GPT-4 for gaps in Stack Overflow’s corpus
V4: adding RAG for attribution and transparency
Why attribution and transparency were critical for developer trust
How the team used simple spreadsheets and subject-matter experts to evaluate answer accuracy, relevance, and completeness
Why Stack decided to sunset conversational search despite heavy investment—what they learned and why it wasn’t wasted
The pivot to data licensing: how Stack Overflow leveraged its 14M+ Q&A corpus to power LLM training and benchmarks
Building industry benchmarks with subject-matter experts to prove Stack data improved LLM accuracy and relevance

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