Rachel
Bender
Co-Founder & CEO at Batesly
"The Buyer on the Other Side of the Demo: What AI Founders Miss When Selling Into Regulated Industries"
"The Buyer on the Other Side of the Demo: What AI Founders Miss When Selling Into Regulated Industries"
Fri May 15 - 9:10 AM EDT/New York (See in local time)
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05/15/2026 9:10 AM
05/15/2026 09:30 AM
America/New_York
#WTGC2026
"The Buyer on the Other Side of the Demo: What AI Founders Miss When Selling Into Regulated Industries"
#WTGC2026
"The Buyer on the Other Side of the Demo: What AI Founders Miss When Selling Into Regulated Industries"
https://www.womentech.net/ringcentral
https://www.womentech.net/ringcentral
"The Buyer on the Other Side of the Demo: What AI Founders Miss When Selling Into Regulated Industries"
"The Buyer on the Other Side of the Demo: What AI Founders Miss When Selling Into Regulated Industries"
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Session: The Buyer on the Other Side of the Demo: What AI Founders Miss When Selling Into Regulated Industries
Most AI founders selling into legal, healthcare, finance, and other regulated verticals are pitching to buyers who are evaluating them in ways the founder doesn't see. As a lawyer and the co-founder of Batesly, I'm in the unique position of selling a legal-tech SaaS into my own regulated industry.This 20-minute talk is a field guide to what regulated-industry buyers are actually scoring during your demo — and what they'll never tell you to your face. I'll walk through the five unsaid objections that kill deals after the call ends, the post-demo legal and compliance review that torpedoes roughly a third of pipeline (and how to pre-empt it), and what proof-of-value really means when the buyer can't share their data. You'll leave with a concrete pre-demo checklist you can use on your next call.
If you're building AI for a regulated vertical, this talk will change what you show in your next ten demos.
Key Takeaways
- The five unsaid objections every regulated-industry buyer is weighing during your demo — and how to surface them before they become silent deal-killers.
- A pre-emptive play for the post-demo legal and compliance review that kills roughly 30% of AI-product deals in regulated verticals.
- A sharper definition of "trust" than the word itself — plus what buyers actually score when they say they need to "trust" you.
- What proof-of-value looks like when the buyer can't share their data with you — three mechanisms that work without requiring data access.
- A 10-point pre-demo checklist you can use on your next call into a regulated-industry buyer.
Bio
Rachel Bender is the founder of Batesly, an all-in-one practice management platform for law firms with AI features, and the owner of Arthouse Legal PLLC, her Seattle freelance practice serving creative professionals. She brings a rare operator-and-buyer perspective to AI-era sales.