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Trent Gillespie

Operational AI Strategist | CEO of Stellis AI | Creator of AI Sprint | Former Amazon Executive

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Trent Gillespie is a seasoned technology leader with over 25 years of expertise in driving innovation and growth across the tech industry. His illustrious career includes nearly a decade as a Senior Technology Executive at Amazon, where he played a pivotal role in spearheading the company’s global expansion efforts across various business units and geographies. 

 

Trent led the Amazon’s Alexa Privacy, Risk, and Compliance function, ensuring the Alexa AI was private and secure globally, and he revolutionized Amazon’s delivery capabilities with AI, while leading it’s Last Mile Technology Innovation team. 

 

Currently, as the CEO of Stellis AI, Trent collaborates with business leaders across industries to unlock growth potential through AI. His deep understanding of AI and technology, coupled with his ethical stewardship, positions him as a prominent figure in the AI landscape. 

 

Based in Seattle, Trent is not only an influential AI keynote speaker but also an active participant in the local tech community, offering consultancy and transformative training sessions that empower businesses to harness AI for sustainable success.

Speaking Topics

Now Or Never: Turning AI Into A Competitive Advantage

Every organization knows AI matters. Very few are turning it into real advantage.


AI agents are rapidly reshaping how work gets done, how companies compete, and what customers expect. While most organizations are experimenting with AI tools, very few are rebuilding how their business actually operates.


This keynote shows why this is a now-or-never moment for their business to operate. Former Amazon AI leader and CEO of Stellis AI, Trent Gillespie gives leaders a clear, grounded view of what’s changing now, where AI is creating real competitive separation, and where organizations risk falling behind.


Two proprietary frameworks anchor the session. The Future Customer™ helps leaders see exactly where their market is heading and what their customers will expect next.


And the AI SPRINT™ gives them a step-by-step operating model to embed AI into strategy, leadership, and daily decisions. Leaders leave with clarity, confidence, and a practical path to move from experimentation to sustained competitive advantage.


Actionable Takeaways Tailored to Each Audience:

  • Understand how AI agents are reshaping productivity, personalization, and customer experience.
  • Identify blind spots in how you serve your next-generation customer and anticipate the shifts AI will create in what they value.
  • Apply the 6-step AI SPRINT™ framework to drive innovation, empower teams, and accelerate results.
  • Build an AI-ready culture where experimentation and learning become a leadership discipline.


Ideal Audience: This program is ideal for leaders at all levels who are shaping strategy, driving operations, and fueling growth in an AI-driven world.

AI At Work: From Curiosity To Capability

AI is no longer a future concept – it’s a daily advantage.


AI is reshaping the workplace, and the rise of AI agents is accelerating how work gets done while also transforming how businesses operate and compete. Agents are beginning to handle tasks, coordinate workflows, and even participate in decisions—changing how companies create value and how people contribute. This moment is creating a major opportunity for employees who learn how to harness AI effectively.


In this engaging keynote, Trent Gillespie helps teams move from curiosity to real capability by making AI practical, relevant, and immediately useful.


Drawing on his experience leading AI innovation at Amazon and advising companies on real-world adoption as the CEO of Stellis AI, Trent shows employees how to use AI to reduce friction, improve output, strengthen problem-solving, and create more value in their roles. With live demonstrations, practical instruction, and a clear path to action, this presentation builds the confidence and momentum teams need to work effectively with AI—and AI agents—in the new world of work.


Actionable Takeaways Tailored to Each Audience:

  • Tailored to Each Audience: Understand how AI is reshaping work, business models, and required skillsets.
  • Move from curiosity to capability—learn practical ways to use AI to improve speed, quality, and output.
  • Learn how to eliminate routine work, reduce bottlenecks, and free up time to unlock higher-value productivity.
  • Use AI as a thinking partner to strengthen problem-solving, explore ideas, analyze information, and generate better outcomes.


Ideal Audience: This program is ideal for ideal for all employees ready to learn, apply, and get value from AI in their everyday work.

The AI Flywheel: Building A Durable Innovation Empire

Many organizations make early progress with AI but struggle to sustain momentum.


Initial wins fade. Pilots stall. Progress slows. Innovation fades. The companies that succeed in the AI era will be the ones that build systems where improvement compounds over time. In this advanced, executive-level program, Trent Gillespie reveals how Amazon built one of the most powerful innovation engines in the world—and how leaders can apply those same principles using AI. Through his AI Flywheel™ framework, Trent shows how organizations can turn operational gains, learning, and customer insight into a self-reinforcing cycle of innovation and growth.


Drawing on Amazon’s Working Backwards approach and the Future Customer™ framework, leaders learn how to align teams, build feedback loops, and continuously reinvest AI-driven gains to accelerate innovation. The result is a practical model for turning AI from isolated initiatives into a durable engine of innovation and long-term competitive advantage.


Actionable Outcomes:

  • Understand how the AI Flywheel drives continuous innovation Build a self-reinforcing AI Flywheel™ that compound results over time.
  • See how the Future Customer™ focuses innovation on where markets are heading.
  • Apply Amazon’s Working Backwards approach to accelerate AI innovation.


Ideal Audience: This program is ideal for senior executives at larger organizations who are ready to move beyond understanding AI and focus on reshaping their structure, strategy, and culture to drive innovation.

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Testimonials

"Trent’s keynote was inspiring, insightful, and refreshingly provocative—clearly outlining how to build healthcare organizations that effectively leverage AI, with an enlightening look into Amazon’s bold healthcare strategy."

"Trent Gillespie delivered one of the most compelling and actionable sessions of ASAE’s CEO Conclave. His pragmatic approach to AI—grounded in real-world experience and Amazon’s “future customer” philosophy—cut through the hype and offered a clear, CEO-ready framework for how associations can evolve to meet the needs of tomorrow’s members. Trent’s insights were not only visionary but also immediately applicable, empowering leaders to think boldly and strategically about AI integration. Trent’s session was a masterclass in future-focused leadership.”

“That was alarming, informative, and inspiring all at the same time. And that's a rare presentation that can capture all three of those. And for sure, access of what I wanted was a catalyst to think differently about what we're heading, and you definitely hit the mark there.”

“Trent’s day-long seminar was one of the most impactful things I've done for my career and company since I can remember.”

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