Trent Gillespie on AI Acceleration and Empowering Innovation at Every Level

When Trent Gillespie speaks about the future of work, people listen. A former senior executive at Amazon, Gillespie helped steer some of the tech giant’s most transformative AI and operational initiatives, programs that didn’t just scale globally, but rewired how the company thought about innovation from the inside out.

Today, Gillespie is a globally sought-after speaker and advisor, known for his unfiltered, practical insights on technology, leadership, and building innovation-ready organizations. His philosophy? That true transformation doesn’t start with software or data—it starts with people.

In this exclusive interview, he reflects on lessons from Amazon, explores the future of artificial intelligence in the workplace, and explains why empowering employees to innovate is essential.  

His hands-on approach makes him a go-to choice among forward-thinking innovation speakers.

During your time at Amazon, what actually worked when it came to using AI as a real business advantage, and what should companies stop pretending works if they want to see real impact today?

Gillespie: So, there were many lessons that I learned at Amazon about how to use AI for its business success because I think that Amazon really used AI as its competitive differentiator throughout its entire business.  

It was one of the first companies to use artificial intelligence in old-style machine learning when it created Amazon’s recommendations. And now, that’s still what powers everything. Of course, there’s Amazon Alexa, but how you get your deliveries on time, how it gets lower prices — it’s used AI for all of those.  

One of my projects was making Amazon Fresh profitable for the first time, and we did it by using AI. It was able to figure out the deliveries and best route drivers around, and again, that’s what made it successful. When we got to that point, we took that and extended Amazon Fresh throughout the world again using those capabilities. 

The other thing I think about here is that every company now has the ability to use AI in its organisation because the costs have come down. Amazon invested billions and billions of dollars in it. Now, because of generative AI, it’s more within reach, so any organisation is now able to learn some of, or take some of, Amazon’s lessons and apply them. 

Amazon’s known for being relentless about innovation. What principles or habits from your time there do you think other companies should actually be borrowing if they want to keep up in the AI era?

Gillespie: Oh, there are so many. I think of maybe two of them. The first one is making an innovative company where anybody can innovate. So, when you think about most organisations, they’ve often got like a technology team or an innovation team or a technology guy responsible for figuring out new technology and applying it in the company. And frankly, that’s just going to be too slow now.

With artificial intelligence, everybody has these AI agents available to them. And what we learned at Amazon is when you give everybody the expectation and empower them to do innovation, it creates significant advantage.

I mean even in today’s organisation, if you can empower your employees to save five minutes per day in their tasks over an entire year, that adds up to your organisation being 26% more efficient. And so, take that lesson from Amazon — empower everybody to use AI and be innovative and you’re going to leapfrog the competition.

And then there’s another point that I think is really important to businesses to consider from how Amazon has been, and that is to build for your future customer.

Amazon always considers what customers will want in five to seven years. So, they manage their current business well and invest significantly today to prepare for what their future customers will want.

I think that’s a really great lesson for most businesses because you can do the same thing today in your industry. Start thinking about that future — what are you going to want? What will your customers want in the future? And then start building it, and you will beat your competition and create many amazing products.

As AI adoption accelerates, many companies seem nervous about security and privacy when it comes to AI. Is that fear justified, or are we overcomplicating it?

Gillespie: There are a lot of misconceptions out there around AI right now, and maybe not even as many misconceptions as people just do not know what to do because it’s brand new. We’re all trying to figure it out together. I don’t think there’s even a person on the planet who knows exactly the right thing to do, so it’s okay if you’re not clear.

The top question that comes up in my talks almost every single time is: Is it secure, and is it private? Now, I think of it just like any other business-level system you use in your organisation today. If you’ve bought the business version from a reputable company, it will be private and secure, like your Gmail or Microsoft Outlook.

It will be secure to the same level as those types of tools. But make sure that your employees are using it under the business account because what I find in working with companies every single day is most companies right now — they haven’t given all of their employees access to these tools.

I just surveyed an organisation to figure out their attitudes and impressions of using AI before we rolled it out, and about 40% of their employees were already using AI before the company said it was okay. That’s a huge deal — opening up your organisation to some risk. So, make sure, if you’re worried about privacy and you want to get the benefit of these AI tools, that your employees use the proper version that is secure and private and under your business.

There’s this myth that AI just ‘works’ once you turn it on. What’s the reality when it comes to actually getting teams to use it effectively?

Gillespie: And that is also the second misconception, that you think you might immediately get a lot of value out of AI. You will only do that if your business supports it and trains employees, because many employees will dabble with it. You’ll get maybe 10-20% of them that will love it and do well.

The other 80% really need a lot of support to get there. That’s training, knowledge sharing, and, of course, empowering them to be safe doing it. And so, I think that if you just address those two things when you start on your AI journey, you’re going to be tremendously more effective.

Explore more of the AI in the industry series.