WIN WITH AI: How to Build an AI-Enabled, High-Growth Business WITH TRENT GILLESPIE

November 4, 2025

Thanks for attending my keynote talk! 

Here are the additional resources I promised:

  1. Key Slides
  2. GPT Links
    1. Future Customer GPT
    2. Automation Finder GPT
    3. Sales Call Brief GPT
  3. 30 Day Action Plan

Below is the AI summary of the keynote talk.

Finally, here are some links to products I recommend, that include special sign-up discounts for my audiences.

  1. Lindy AI: Personal and Small Team Automation (1 month free)
  2. Read AI: Meeting Notetakers and Information Management (3 months Enterprise free)
  3. Omada AI: Automated SMB Marketing
  4. Gamma AI: AI-Powered Presentations

Need help with AI? Contact Trent


Operationalizing AI: How to Create Growth and Win with AI

Presenter: Trent Gillespie | 40 Strategy Growth Workshop

The Conference Room Moment

Trent opened with a personal story from his third day at Amazon. Called into the VP's office, he expected the worst. Instead, he was asked to "fix Amazon's global growth"—a role he wasn't hired for and knew nothing about. In that conference room, he faced a choice: let fear win and pass the opportunity to someone else, or step up and lead anyway, ready or not.

That single decision changed his entire career. It enabled him to lead Amazon's expansion from London to Dubai, reinvent last-mile delivery, define global privacy standards for Alexa, and eventually know more about Amazon's business strategy than anyone except Jeff Bezos.


The First Big Mistake: Treating AI as Just Another Tool

Trent emphasized that AI is not another tool rollout or CRM upgrade—it is your new operating system. It's a complete rewiring of your business that will:

  • Change your products and services
  • Transform how you deliver them
  • Alter your cost structures
  • Demand new skills from every employee
  • Change who your customer is

If you learn AI, incorporate it, and lead it as the business transformation it truly is, you'll empower all your employees to be builders of the future instead of bystanders in it.

The Amazon Model

Trent explained that Amazon's success came from two critical factors:

  1. Creating a culture of innovation where every employee was expected and empowered to innovate
  2. Using AI to scale that innovation beyond human ability

The game-changer: With generative AI, these same capabilities are now available to every company for approximately $30 per month per person. You don't need billions of dollars—but you do need leadership, vision, and action.

Current AI Adoption Reality

When Trent asked the room who uses AI daily, two-thirds raised their hands—significantly higher than most business audiences. The data on AI usage reveals critical insights:

  • 40% of knowledge workers are using AI in their jobs (even without authorization)
  • Daily AI users report 20% productivity improvements and better quality work
  • Weekly users see minimal benefit
  • Less frequent users see no benefit

Key takeaways: People are finding real value in AI tools (that's why 40% use them despite policies). **Daily use is essential for competitive advantage.** If your organization isn't empowering AI use, you're leaving opportunity on the table and creating risk through shadow IT.

Why Giving Employees AI Isn't Enough

Trent clarified a critical misconception: simply giving employees AI tools won't reinvent your company. It will make them more efficient, but it won't change your products, services, or competitive positioning. For that, you need vision.

The Amazon Vision Method

At Amazon, vision came from one relentless question: What will our future customer want five years from now? The team would imagine that future and work backwards to build it before anyone else did. This approach created products like the Kindle and Alexa.

Vision is critical right now because customer expectations are already changing. A recent survey found that 58% of consumers are replacing search engines with generative AI tools—yet very few businesses are visible in AI search results or set up to service AI agents.

The Second Big Mistake: Optimizing for a World That No Longer Exists

Leaders are using AI to improve processes created 5, 10, or 20 years ago—instead of reinventing those processes with AI at the center for how business needs to work in this new AI-enabled world.

Trent introduced a framework of questions to help organizations develop their AI vision, starting with: What do your customers value most about your company today? He asked attendees to identify three specific things customers have told them they value (not assumptions), then explained they would revisit these answers after understanding what's happening with AI.

What Changes When Intelligence Becomes Cheap?

For all of human history, intelligence has been what we've paid the most for. We've built entire organizational structures—sales, operations, finance, customer service—around routing decisions through intelligent people, hoping for intelligent outcomes.

Now intelligence is instant, on-demand, and approximately $30/month.

Trent compared it to electricity, but for thinking. Sam Altman noted that as data center production gets automated, the cost of intelligence will approach the cost of electricity—and we're already seeing these costs converge.

Live Demonstration: Building an Application in 15 Minutes for $1.45

To illustrate what cheap intelligence means, Trent demonstrated building a customer reactivation application:

  1. Asked ChatGPT to design a web application that identifies customers who haven't ordered in 90 days and creates personalized reactivation campaigns
  2. Copied the requirements to Replit (an AI-powered development platform)
  3. The AI built a functional application with a dashboard, customer import capability, campaign creation, and email merge features
  4. The AI tested itself by navigating through the application to confirm everything worked

The reality check: Most organizations would take 6 months to a year to decide to build such an application. Trent built it in **15 minutes for $1.45.** When every employee can solve problems and build solutions for less than a cup of Starbucks, it changes everything. The only question is: which of your competitors will empower their people to do this first?

The Future of Work: AI Agents Everywhere

General Purpose AI Agents

Trent explained that employees will soon work primarily through general purpose AI agents that become the interface to their entire workday—not just for writing emails, but replacing CRM systems, email platforms, and Microsoft Office entirely. These tools were built to track human activity, but when AI agents do the work, we don't need the same software.

General purpose agents are like Swiss Army knives—trained on all the world's information and good at many things, but not perfect at your specific processes.

Specialty AI Agents

For perfection in your specific workflows, you need specialty agents (the power tools) connected to your data and trained on your processes:

  • Outside sales agent: Knows your ideal customer types
  • Pricing agent: Optimizes pricing by customer, region, and market conditions
  • Forecasting agent: Predicts future needs for inventory placement
  • Replenishment agent: Orders against forecasted inventory automatically

Some of the biggest organizations now have more AI agents than employees. These agents are available to all ChatGPT users today and cost as little as $50/month per person.


Live Agent Demonstration

Trent demonstrated ChatGPT's agent capability by asking it to open his CRM (HubSpot) and schedule a follow-up task. The AI:

  • Opened a virtual computer in the cloud
  • Navigated to HubSpot and found the login page
  • Logged in using provided credentials
  • Searched for and found the correct contact
  • Figured out how to create a task
  • Selected a custom date from the calendar

All from a simple natural language prompt—no coding or technical knowledge required.

Reinventing Sales: Agent-Based Prospecting

Trent outlined a multi-agent prospecting system he's building for clients:

1. Prospecting Agent

Searches the entire internet for potential leads matching your ideal customer profile. Can have real-time conversations to qualify interest.

2. Qualifier Agent

Trained on your company, products, service areas, and ideal customers. Filters leads based on geography, size, and fit.

3. Research Agent

Finds everything available about qualified prospects—quarterly statements, news releases, LinkedIn profiles—and consolidates it into comprehensive research reports.

4. Strategy Generator

Combines research with your company's value proposition to create hyper-personalized sales strategies for each specific lead.

Result: Sales teams arrive at work with pre-qualified leads, fully researched, with personalized strategies ready to execute.

Building Agents with Lindy

Trent introduced Lindy, a personal AI automation tool that uses natural language to build agents. Example prompt: "Each Monday, check my CRM and emails for accounts that haven't ordered in 90 days, then draft personalized re-engagement emails."

The tool creates a visual workflow you can customize by dragging and dropping connections to your email, CRM, and other systems—costing around $50/month.

The Agent-to-Agent Economy

Trent delivered a crucial warning: your customers will have AI agents too, and those agents will decide if your company makes the cut. Your customers may never browse your website, call, or email you again.

How Agent-to-Agent Commerce Works

  1. Customer asks their AI agent: "Find 20 units of [part number]"
  2. Their agent searches the internet (human web or new agent-to-agent networks being built)
  3. Finds your inventory agent, which responds: "100 in stock, $75 each, 24-hour delivery"
  4. The agents communicate, potentially complete the purchase, while keeping humans informed

Timeline: This is approximately **6 months away** from mainstream adoption, not 5 years. Organizations are actively building this infrastructure right now.


The Opportunity: Personalized Customer AI Agents

Instead of one chatbot for all customers, create an individual AI agent for each customer trained on everything you know about them: order history, credit lines, challenges, preferences. This agent can:

  • Proactively offer installation assistance
  • Provide predictive analytics on their operations
  • Notify them of better deals or special options
  • Turn your organizational intelligence into a value offering

AI Visibility Crisis

Trent introduced SparkToro (a new tool) that measures your company's visibility in AI applications. In one example, a $150 million company—well-known in their industry—appeared in only 1.7% of queries sent to major AI applications. This visibility gap is consistent across most organizations today.

Revisiting Customer Values in an AI World

After explaining the AI landscape, Trent returned to the opening question about what customers value, adding critical context:

Question 2: Which values still matter when knowledge is free and instant?

Identify which customer values become even more important when AI makes intelligence abundant and instantaneous.

Question 3: What can you no longer charge for?

Determine which services become expected or commoditized because AI makes them freely available to everyone.

Example: Distribution Industry Transformation

Past customer expectations:

  • Call for parts catalog lookup
  • Reliable parts availability and inventory
  • Just-in-time delivery when needed

AI-enabled shift:

  • AI co-pilots handle parts lookup
  • Predictive services anticipate parts needs
  • AI-powered forecasting optimizes inventory placement

Future customer expectations:

  • Self-service AI agents for all transactions
  • Uptime as a service (selling reliability, not just parts)
  • Predictive intervention (parts arrive before they're needed)

Custom GPTs Provided

Trent shared three custom GPTs (available via QR code) to help attendees apply these concepts:

  1. Future Customer GPT: Guides teams through the five-question framework for any company (just input your URL)
  2. Automation Finder: Identifies specific tasks and processes you can automate with AI
  3. Sales Call Brief: Researches prospects and creates personalized sales strategies

Sales Call Brief Demonstration

Trent demonstrated researching an attendee (Ed) using the Sales Call Brief GPT, which provided:

  • Background on Ed's business and industry
  • Implications of how AI will affect his specific sector
  • Leading questions to establish credibility and open meaningful conversation
  • Ability to generate personalized sales scripts based on products and services

What's Left for Humans? Vision.

When intelligence is no longer your limit, imagination becomes the constraint. The human advantage is:

  • Seeing opportunities on the horizon
  • Creating plans to reach them
  • Bringing entire organizations along
  • Thinking and innovating with AI


Critical insight: This isn't just the CEO's job. AI applies to every process in your company, which means your edge comes from people closest to the work—those touching customers and seeing challenges daily. Winning companies are decentralizing innovation, just like Amazon did.

Vision in Action: Real Examples

Plumbing company example: A major bottleneck was looking up parts in catalogs. By scanning catalogs and training AI to read part diagrams, they got employees to the right page with 95% accuracy and the correct part with 80% accuracy—with minimal investment.

AI applications under $500/month:

  • Demand forecasting
  • Competitor tracking
  • Upsell recommendations
  • Dynamic pricing
  • Part finders from diagrams
  • Customer renewal risk radar

Why Trent Does This Work

After nearly nine years at Amazon, Trent took a sabbatical during COVID. He came across a book called The Warehouse—a fictional dystopia about a "cloud company" that got so great at e-commerce, innovation, and AI that it took over the world. The ending was not positive.

This reinforced what Trent was already thinking: he didn't want to just make tech companies bigger for bigger's sake. Instead, he wanted to help as many local companies succeed by learning these concepts and applying them in their businesses and communities.

For three years, Trent has been refining and simplifying these concepts with real clients. What he shares isn't theory—it's what's working on the ground in actual organizations today.


The AI Sprint Framework: Your Complete Project Plan

The best approach Trent sees working in organizations is not one big project, but a rhythm and discipline of AI use called the AI Sprint.

The Monthly Sprint Cycle

Organizations succeeding with AI follow this pattern:

  1. Ask: "What is our best opportunity to use AI this month?"
  2. Try it—take a step
  3. Reflect: "What did we learn?"
  4. Adjust course and take another step
  5. Repeat every month: October, November, December...

This applies at every level—not just leadership, but every employee asking monthly how they can use AI to improve their work.

Critical caveat: Speed without direction is a treadmill to nowhere. Organizations failing to get ROI from AI lack vision. That's why building for your future customer is essential—without it, you're not moving in a direction that helps your organization.

The SPRINT Framework

Trent created a six-step framework (acronym: SPRINT) that serves as the project plan:

S - Spark Action (Leader Education)

Light the fire to finally get AI adoption in your company. At Amazon, the biggest problems weren't solved by people with the biggest titles—there was always one person who said "I got it, I want it" and became the spark.

The problem: Trent has yet to meet a single leadership team aligned on AI in any way—not what it is, who owns it, when to invest, what to invest in, or what the challenges are. This means leadership teams are guessing about their future in different directions.

Three specific actions:

  • Educate leaders on AI: Go hands-on together, not just keynote talks—actual exercises
  • Assign a transformation owner: This is business transformation, not an IT project (IT shouldn't own it)
  • Start transformation sprints: Create the culture of monthly learning and experimentation, starting with leadership

P - Position Your Company to Win with AI

Design your company for serving AI-enabled future customers. You don't just want to use AI—you want to win and grow.

The five future customer questions:

  1. What do your customers value most today?
  2. Which values still matter when know-how is free and instant?
  3. What can you no longer charge for because it's expected?
  4. Where will customers still desire a uniquely human touch?
  5. What brand new value can you create because intelligence is cheap?

Real example: One client decided 18 months ago that 10% of revenue would come from new AI services within three years. They generated 120 ideas, selected 6 top options, and are now investing in 2 brand-new services that didn't exist in their marketplace—and they're not a technology company.

R - Rally Employees to Use AI Daily

You can't force your team into the future or create innovation culture through fear. But you can create an environment where AI use is normal, expected, and supported.

Three essential actions:

  • Create safety and guardrails: Implement AI acceptable use policies so employees know how to use tools safely while protecting company standards
  • Clarify job safety: Address AI job concerns directly. Trent's framework uses AI to create productivity gains that get reinvested into growth—something most employees support because it creates future opportunities
  • Equip and train: Provide business-level AI tools and ongoing training, with incentives for use (recognition, small rewards like $20 gift cards)

Reality check: When Trent asked how many organizations had written AI guidelines, given everyone access, provided training, and offer monthly updates, only 3 attendees raised their hands out of the entire room. That's the real on-the-ground environment—and the opportunity.

I - Integrate (Sales & Marketing First)

Important: Don't do any integration until you've completed the first three steps. That's where companies go wrong.

Start with revenue creation (top line) because it's low cost, low risk, and funds your future:

  1. Marketing: Content creation and personalization (don't send mass emails with dynamic names—create truly personalized outreach)
  2. Sales: Lead scoring and hyper-personalized sales strategies for each prospect
  3. Operations: After revenue is humming, address your biggest bottleneck only, then move to the next one

Your organization can only move at the speed of its slowest part, so focus on removing constraints one at a time.

N - iNnovate (Enable Culture of Innovation)

Every CEO says they want innovation culture. Very few actually achieve it.

Amazon succeeded because it built a culture of innovation and used AI to scale it. Here's the key insight: AI gives organizations a 100% improvement in their ability to innovate—without any training, just by providing the tools.

When you combine AI access with the AI Sprint reflex (monthly experimentation), you create a living, breathing culture of innovation. You replicate Amazon's success with just these two elements.

T - Trailblaze with New Offerings

By this stage, your organization is truly humming—everything is working, everyone is aligned. Now you can invest in building things that answer the final two future customer questions:

  • Where will customers still want a real person they can trust?
  • What can we offer now that wasn't possible before?

Deliver on these through the AI Sprint—incrementally, step by step, not one big project.

QUOTATION BOX (fafafa, border: ddd)

"Lasting advantage can only come from building for your future customer."

The Day One Philosophy

Trent closed with Amazon's concept of "Day One"—the idea that if you start every single day with the same hunger to make a difference as you did on your first day of work, the same passion to solve customer problems, and the same courage to take calculated risks, then you can change the future.


Action Items

  1. Use AI daily yourself if you haven't started already
  2. Access the provided resources (QR code for slides, custom GPTs, 30-day action plan)
  3. Schedule hands-on AI training with your leadership team
  4. Assign a transformation owner for your AI initiative
  5. Complete the five future customer questions exercise
  6. Create AI acceptable use policies and address job safety concerns
  7. Begin monthly AI sprint cycles at all levels of your organization

QUOTATION BOX (fafafa, border: ddd)

"Today is your day one to use AI—not just to write an email, but to spark new ideas, reinvent processes, redefine your entire industry, create something new that creates jobs locally and enhances your communities. You've got the best tools to do this that humans have ever invented. And today, you've got your moment."