RAG in the Real World
Why RAG systems that look strong in demos break down in production and how technical leaders are designing architectures that return reliable, usable results at scale.
GILD Roundtable for Technical Leaders | Austin, TX
May 26th, 2026 · 6:00–8:30 PM
Presented in Partnership with Tecla
Helping AI-forward companies hire elite talent across product, engineering, and growth.
Food and drinks for the evening are generously provided by Tecla.
About the Roundtable
Retrieval-augmented generation looks strong in demos.
In production, it often degrades.
Retrieval fails quietly.
Indexes drift.
Context windows collapse.
Outputs become inconsistent or subtly wrong.
This closed-door GILD roundtable brings together senior technical leaders actively operating RAG systems in production to compare:
What actually holds up at scale
Where retrieval breaks despite strong evals
How teams are debugging and preventing regression
Evening Agenda
6:00–6:30 PM
Arrival & Mingling (food and drinks provided)
6:30–6:45 PM
GILD Welcome + Partner Introduction
6:45–7:00 PM
Short Framing Discussion
7:00–8:00 PM
Roundtable Discussions
• 3 rounds
• 18 minutes per round
• 2-minute rotations
8:00–8:30 PM
Open Mingling
Roundtable Prompts
Round 1: Where RAG Quietly Fails
In production, where does retrieval or grounding break in ways that demos and offline evals didn’t catch?
Round 2: Architectural Tradeoffs That Matter
Which decisions around chunking, indexing, embeddings, reranking, or caching most impacted reliability at scale?
Where did you optimize for demo performance and later redesign for production stability?
Round 3: Designing for Reliability Over Time
How are you detecting drift, preventing silent quality regression, and structuring human oversight without destroying throughput?
What does “production-ready” mean to you now that it didn’t six months ago?
Who Will Be in the Room
Curated for senior technical leaders building production AI systems:
CTOs
Heads of Engineering
AI & Platform Leaders
Senior architects operating RAG systems
Attendance is intentionally limited to keep the room candid and high-signal.
Privacy & Experience Standard
Chatham House Rules apply.
Discussion stays private. This is what unlocks candor.
Expect an intimate, thoughtful environment with elevated food and drinks throughout the evening.