Why Most AI Pilots Fail - And How to Make Yours Succeed

Why Most AI Pilots Fail — And How to Make Yours Succeed

Insurance organizations are investing heavily in AI. Pilots are launched, proof-of-concepts are presented, and then — quietly — most of them stall. They don't fail loudly. They just never make it to production.
The problem usually isn't the AI. It's everything around it.
Integration complexity, process dependencies, accuracy gaps, and the reality that most AI tools require you to change how you work before they deliver any value — these are the patterns that kill pilots before they scale.
This session examines what separates pilots that die in proof-of-concept from automation that reaches production and delivers measurable results.

What You'll Learn
Why AI pilots stall before production — and how to identify the warning signs early
What separates a promising demo from a workflow that runs reliably at scale
How to design for production from day one, without costly integrations or process overhauls
How to measure whether automation is actually working

Featured Speakers:

Sasha Haco
Sasha Haco is Co-Founder and CEO of Unitary, an AI automation company building Virtual Agents that handle complex operational workflows with human-level precision. Before founding Unitary, Sasha completed her PhD in Theoretical Physics at the University of Cambridge, where she worked alongside Stephen Hawking, Malcolm Perry, and Andrew Strominger on the black hole information paradox. Her research on black hole entropy and soft hair was published in the Journal of High Energy Physics, and she was featured in the 2020 Netflix documentary Black Holes: The Edge of All We Know. She brings deep technical rigor and operational focus to making AI automation reliable enough to trust at scale.

Kyle Ramsey
Kyle Ramsay is Chief Product Officer and Head of AI at Hippo Insurance, where he leads company-wide product and AI strategy across complex, highly-regulated insurance domains while delivering effortless customer experiences. He has a 13-year track record building consumer products from 0-to-1 features to scaled growth engines, spanning growth, engagement, retention, and monetization. Before Hippo, Kyle built new businesses and products at NerdWallet in investing, banking, and personal financial management, and started his tech career on LinkedIn’s Growth team. He holds a degree from Wake Forest University and is based in San Francisco.

Hosted by InsurTech NY in partnership with Unitary. Free to attend. Registration required