The AI Speaker Who Delivers.

Your audience has heard the AI hype. They've sat through the breathless predictions and the vendor pitches dressed up as keynotes. What they haven't had — until now — is someone who can make AI feel real, relevant, and actually doable for the organization they lead.

Trent Gillespie is a former Amazon executive who left one of the world's most powerful AI companies to serve the organizations it was disrupting. He brings that insider perspective to every stage he walks onto, and he translates it into something your audience can act on before they leave the room. Not someday. Monday morning.

From small rooms of executives to groups of 5,000 or more, spanning financial services, to healthcare, to real estate, the feedback is remarkably consistent: this is the clearest, most actionable session on AI they've ever experienced.

Trent Gillespie
Audience Impact
★★★★★
4.8 / 5
Value delivered
★★★★★
4.8 / 5
Overall enjoyment
★★★★★
4.7 / 5
Actionability
2,147+
Audience ratings recently submitted
"Trent delivered one of the most compelling and actionable sessions of ASAE's CEO Conclave. His pragmatic approach — grounded in real-world experience and Amazon's 'future customer' philosophy — cut through the hype and offered a clear, CEO-ready framework. Trent's session was a masterclass in future-focused leadership."
Morgan MaravichVice President, ASAE Research Foundation
Keynote Feedback
What Audiences Say
This is the FIRST and only AI talk with actual good info. All other AI talks just tell us why AI is the "next best thing." Thank you for actually making it matter!
Kim AllisonCEO — ASAE CEO Conclave
It was motivational and actionable. Most try to hype you up but don't give you actionable steps.
Michael JacksonSVP & Chief Innovation Officer, TCFCU
Best discussion on introducing AI to an organization that I've seen out of many.
Doug WrightCEO — NACUSO 2026
It legitimately made me re-think our strategy for 2026. I assumed the operation would be fine — it's not going to be fine unless we make some changes.
Nate AndersonPresident & CEO — CA Association of Realtors
So amazing — gave me such great insight on the questions I need to be asking my team. I could have a whole masterclass on this topic!
Jennifer BrydgesPresident, AMPED Association Management
A necessary wake-up call with clear actionable items.
Henrik WalterCEO — PTDA Annual Summit
The best, most forward-thinking presentation I attended with regard to the use of AI in organizations.
Elisa RossVP of Marketing, Hughes Federal Credit Union
It helps you see an overwhelming tsunami of opportunity, while also giving you the tools to soar through it.
Haley CoxExecutive Director — ASAE CEO Conclave
That was alarming, informative, and inspiring all at the same time. A rare presentation that can capture all three.
Dave MortonVP, Husky Technologies
This is the first keynote on AI that was actually useful and actionable. Thank you!
Lily DavidsonSVP of Association Management, Etherio
Best talk I've heard in a while. The path is no longer foggy.
Justin HeymanCOO, CMP Management
One of the best keynotes I've heard in years.
Carolyn PricePresident, CMP Management
In Their Own Words
Unfiltered Audience Reactions
Executives on taking action
I wish my whole leadership team could hear this.JJ Colburn, co-CEO — Strategic Association Management
I am going to take my leadership team through the slides.Don Lindsey, CEO — 40 Strategy
Absolutely the best keynote with practical instruction. I will be "re-presenting" to my leadership.Raju Patel, CEO
Hire this guy to come talk to your group!Scott Grimes, Partner — Mattison Corp
Every CEO should hear this talk.Bryan Keller, CEO — Benesch
On what makes it different
I started texting my clients during the talk. Wildly inspiring.Steve Lucas, CEO & Founder — NatCon 2026
It gave me a sense of what is truly happening in AI — as opposed to what is just being imagined.Rachel Willis, VP of Innovation
Plain English. Made AI make sense.Jeanne Sheehy — ASAE CEO Conclave
It is not a sales pitch — more informative and actionable.Tim Gray — Encore Global
Most impressive session I've attended at any conference.Lon Varns, President — NACUSO 2026
Audience Impact
The Moment It Lands
This is just what I needed to hear at this moment in my career.
Angela HoltCEO — NatCon 2026
It opened my eyes to a number of future possibilities in my organization.
Kireem SwintonInterim President & CEO — ASAE CEO Conclave
Motivational. Will increase our speed of AI implementation.
Bart WatsonPresident & CEO, Brewers Association
It made us rethink how we approach innovation. AI is not an IT initiative — it's a cultural shift.
Ken CerneyHealth Insights
Trent properly challenged all of us to lead with vision and start now.
Tom CangelosiCOO — Distribution Strategy Group
It took the fear out of using AI and inspired me to experiment with my ideas more.
Alisha WhiteGlobal Sales Director — ASAE CEO Conclave
Find Trent, listen, be inspired, and take action.
George SandmannPresident — 40 Strategy
It sparked the vision for how I can use AI — as opposed to a large unknown.
Edward BronnenbergSVP — NACUSO 2026
We're still talking about your talk four months later.
J.D.Government Technology Director
Pattern Analysis
Themes That Emerge From 2,147 Responses
Actually Actionable
Audiences leave with a clear next step — not just inspiration
🎯
Industry-Tailored
Custom examples for each audience — not a generic AI overview
🧭
Cuts Through Hype
Consistently described as "finally an AI talk that tells the truth"
🔥
Creates Urgency
Leaders leave with competitive urgency — and a plan to act on it
Reach
Industries Served
Associations & AMCs Credit Unions Banking & Financial Services Private Equity Industrial Distribution Manufacturing Logistics & Supply Chain Mental Health & Behavioral Health Healthcare Real Estate & Property Management Construction & Engineering Automotive & Transportation Hospitality & Events Professional Services Nonprofit
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Via Michelle Joyce Speakers  ·  Tracy Cotton  ·  (310) 902-5568
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