Why Human in the Loop Is Key
Automation in 2026:
Why Human in the Loop Matters More Than Ever
How CEOs, founders, and COOs can redesign workflows, reduce errors, and scale automation responsibly while keeping human judgment at the center.
Gild Curated Circuit in Austin, TX
Date & Time: Tuesday, February 24, 2026 · 6:00–8:30 PM
Presented in partnership with Tecla
Scale your teams and build your AI projects with top nearshore talent trusted by Austin’s fastest-growing companies.
About the Dinner
Automation is spreading across every part of the business. AI now writes, codes, summarizes, forecasts, and powers workflows that used to depend entirely on people.
For leaders, the question is no longer whether to automate.
It is how to design automation that improves quality, increases speed, and strengthens decision-making without introducing new risks.
Joining the conversation is Doug Gray, CTO for Amazon Business, leading teams responsible for product development, sales enablement, and global deployment of Amazon Business technology that simplifies how organizations purchase. His work applies governed data, analytics, and generative AI to help modernize procurement into a more autonomous, insight-driven model.
Previously, Doug joined Indeed as Head of Engineering in 2008, when it was an up-and-coming challenger in U.S. job search. He spent the next 13 years leading engineering through hypergrowth as Indeed became the #1 job site in the U.S. and later the world.
This private GILD dinner brings together a small, curated group of CEOs, founders, and COOs for an off-the-record conversation about:
Where automation creates real leverage
Where human judgment remains essential
How leaders are redesigning workflows, roles, and accountability for 2026
Just operators sharing what is actually working and what has broken as automation expands across their organizations.
Evening Agenda
6:00–6:30 PM
Arrival & mingling
Food and drinks available throughout the evening
6:30–6:45 PM
GILD welcome + brief sponsor introduction
6:45–7:05 PM
Short framing discussion
Setting context on automation, risk, quality, and human oversight
7:10–8:05 PM
Curated breakout discussions
3 rounds
~15–20 minutes per round
Small peer tables with rotation between rounds
8:05–8:30 PM
Open mingling
Continue conversations and build peer relationships
Breakout Prompts (All Tables)
All tables discuss the same prompt during each round.
1. When AI-driven decisions inside your product or operations fail, who is ultimately accountable — and how have you designed human oversight without destroying speed, margins, or competitive edge?
2. Where has embedding automation materially changed cost, speed, or margin, and where did removing humans create unexpected risk, fragility, or customer trust issues?
3. What are you technically capable of automating today but are intentionally choosing not to, and what would need to be true for you to cross that line?
Who Will Be in the Room
This dinner is reserved for senior company operators with real responsibility for execution and outcomes, including:
CEOs
Founders
COOs
Presidents and owners accountable for operations and performance
Attendance is intentionally limited to keep the room curated, 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.