Investing in Transportation and Logistics with AI

Presenter: Trent Gillespie | Benesch Conference: Investing in the Transportation and Logistics Industry

The Conference Room Moment

On his third day at Amazon, Trent was called into the VP's office and asked to "fix Amazon's global growth"—a role he wasn't hired for and knew nothing about. That one decision to step up and lead changed his entire career, enabling him to drive Amazon's expansion from London to Dubai, reinvent last-mile delivery, and define global privacy standards for Alexa.

The Two Big Mistakes Leaders Make

Mistake #1: Treating AI as an IT Project

AI isn't a tool rollout—it's a leadership challenge and complete business rewiring that will change products, services, cost structures, and potentially customers. Handle it as the transformation it is to unlock value and give people purpose as builders of the future.

Mistake #2: Optimizing for a World That No Longer Exists

Leaders are improving processes built 5-20 years ago instead of reinventing them with AI at the center—that's what's required for real benefits.

The Amazon Success Formula

Amazon's success came from creating a culture where everyone was empowered to innovate, then using AI to scale that innovation beyond human ability. With generative AI at $30/month, you no longer need billions of dollars—but you do need leadership, vision, and action.

Current AI Reality

Daily AI users report 20% productivity improvements, while 40% of knowledge workers use AI without authorization. Get AI out of the shadows and empower its use—but giving employees AI alone won't reinvent your organization. For that, you need vision.

The Amazon Vision Method

At Amazon, vision came from one question: What will our future customer want five years from now? The team imagined that future and built toward it. This mindset is critical now because 58% of consumers have replaced search engines with AI tools, yet very few organizations are set up to serve AI agents.

What Changes When Intelligence Becomes Cheap?

For all of human history, intelligence has been what we've paid the most for. Now it's $30 per month, on-demand, and instant—like electricity for thinking, except AI watches, monitors, and takes action.

Live Demonstration

Trent demonstrated building a carrier capacity discovery application in 15 minutes for $2.13. While organizations spend months deciding whether to build such tools, the demonstration got it functional in minutes. When something this powerful costs less than a cup of Starbucks, the question is who will use it first.

The Agent Economy in Transportation and Logistics

Workers will use general purpose AI agents as the primary interface to their workday, potentially replacing email and CRM systems. For logistics operations, organizations need specialty agents for forecasting, pricing, routing, and maintenance.

Agent-to-Agent Commerce

A customer needs Chicago to Dallas capacity. Their AI agent finds your sales AI agent, which responds: "2 trucks available. $2.42/mile. 9 a.m. pickup. 97% on-time." The agents communicate and potentially complete booking while keeping humans informed. Your customers may never call or visit your website again—their AI will decide if you make the cut.

Amazon's Dispatch AI Agent: Manage by Exception

Amazon built a dispatch AI agent that monitors drivers on the road, only alerting human dispatchers when intervention is needed—incidents, major delays, exceptions requiring judgment. This is "Manage by Exception"—the process that will be followed as we move to AI work supervision. AI handles routine monitoring; humans focus on exceptions.

Mission Genesis: The Government AI Initiative

On November 24th, President Trump signed an executive order launching Mission Genesis—explicitly comparing it to the Manhattan Project.

What Is It?

The federal government is building the American Science and Security Platform—the world's most powerful AI engine for scientific research, connecting decades of federal data to supercomputers. The goal: Double productivity and R&D output across manufacturing, supply chain, materials, energy, and biotech within 10 years.

Six Key Components

1. Shared national computing infrastructure (DOE supercomputers + secure cloud)
2. Data standards and secured flows making federal datasets accessible
3. Robotic laboratories and AI-directed manufacturing (demonstrating capability by late summer)
4. AI agents running experiments autonomously
5. Predictive models purpose-built for supply chain, materials, energy, and mobility
6. Energy infrastructure innovations changing facility and fleet economics

Impact on Freight and Logistics

Research areas transforming operations: advanced manufacturing changes what gets shipped, biotech requires specialized supply chains, critical materials mean lighter loads and stronger containers, nuclear/fusion energy changes all energy economics, and semiconductors enable sensors everywhere.

Four Directional Signals for Your Business

What's Left for Humans? Vision.

When intelligence is no longer your limit, imagination is. The ability to see what customers need, choose the path to get there, and bring the organization along is the human advantage at every level. Your edge comes from people closest to the work who understand customer problems.

The AI Sprint Framework

The best approach is a monthly rhythm: ask "What can we do with AI this month?" Try it, learn, share across the organization, and take another step. This creates acceleration through continuous improvement.

The Six-Step SPRINT Framework

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Action Items

1. Start using AI daily yourself
2. Identify your transformation owner
3. Educate leadership hands-on together
4. Assess your data quality and interoperability (critical for Mission Genesis impact)
5. Create AI acceptable use policies
6. Begin planning for agent-to-agent commerce visibility
7. Start monthly AI sprint cycles
8. Train your workforce on AI literacy—it's now a competitive requirement

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Closing

When Trent thinks back to his third day at Amazon, he had no business leading what he did. But he said yes anyway. He was able to figure it out, and it changed his career. Right now, every transportation and logistics leader faces their own conference room moment. AI has put that opportunity on your desk. Mission Genesis is accelerating the timeline. Your customers are adopting AI agents. Your competitors are building capabilities.

You may not feel ready—but that's not the question. The question is: Will you lead?

Thank you to Benesch for sponsoring this important conversation about the future of transportation and logistics.