AI as a leadership challenge by‍ TRENT GILLESPIE

February 3, 2026

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  1. Key Slides
  2. ‍Below is the AI summary of the keynote talk.

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AI as a Leadership Challenge: The Six-Step Sprint to Win Your Future Customer

Presenter: Trent Gillespie | Encore Summit, February 3, 2026

The Conference Room Moment

Trent opened by sharing his transformative experience at Amazon—on his third day, the VP asked him to fix Amazon's global growth despite having no background in e-commerce or international expansion. That single decision to lead before he was ready changed his entire career, enabling him to lead Amazon's expansion from London to Dubai, reinvent last-mile delivery, and define global privacy standards for Alexa.

The parallel to today: AI represents the same conference room moment for every leader. Most aren't prepared, but preparation isn't the question—leadership is.

The Two Big Mistakes Leaders Make

Mistake #1: Treating AI as an IT Project

AI isn't a tool rollout or CRM upgrade—it's a complete rewiring of business operations that will change products, services, delivery methods, cost structures, required skills, and potentially even customer identity. The message: This is a leadership challenge, not a technology project.

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

Leaders are using AI to make small improvements to 20-30 year old processes instead of reinventing those processes for AI-enabled future customers. Incremental optimization misses AI's transformative potential.

Current AI Adoption Reality

At Encore, approximately 60% of attendees reported daily AI use—significantly higher than typical organizations. Research shows:

  • Daily users: 20% productivity improvement and better quality work
  • Weekly users: 5% improvement
  • Less frequent: No measurable benefit
  • 40% of all employees already use AI at work, even without approval

Key takeaway: Get AI out of the shadows and empower widespread adoption, or risk leaving value on the table and creating security vulnerabilities.

The Amazon Vision Method: The Future Customer Framework

Amazon disrupted industries by asking one relentless question: "What will our future customer want five years from now?" They worked backward from that vision to build solutions before competitors could react—creating the Kindle, Alexa, and reinvented e-commerce.

Trent adapted this into a five-question framework for any organization:

  1. What do your customers say they value most about your service today?
  2. Which of those values still matter when intelligence is cheap and instantly available?
  3. Which values can you no longer charge for because they're expected?
  4. Where will customers still want a real person they can trust?
  5. What can you offer now that has never been possible before because AI enables it?

Critical insight: 90% of B2B buyers already use generative AI in procurement. Customer behavior is moving faster than most business strategies, and few businesses are even visible to AI search yet.

What Changes When Intelligence Becomes Cheap?

Throughout human history, intelligence has been the most expensive resource—driving organizational structures, hiring decisions, and compensation models. Now it's available on-demand, 24/7, for $30/month. Sam Altman predicts the cost of intelligence will approach the cost of electricity as data center production becomes automated.

Live Demonstration: Custom Run of Show Application

Trent demonstrated this concept by having Microsoft Copilot design a run-of-show analysis application, then feeding that design to an AI agent that built the complete application in three minutes for pennies. The application included:

  • Risk detection identifying 8 high-risk elements in a 19-segment show
  • Intelligent flagging (unassigned panel discussions, live software demos, quick transitions, remote participants)
  • Visual timeline of the complete run-of-show
  • Automated show caller script with audio/video/voiceover cues
  • Crew-specific update sheets for AV, lighting, and other team leads

The transformation: What traditionally takes organizations 3-12 months to decide to build can now be designed and deployed in minutes. This isn't productivity improvement—it's complete reinvention of work.

Reinventing Processes with AI at the Center

Real example: When Amazon launched delivery in Tokyo, drivers plotted routes on paper maps in the world's most dense city—chaos. Trent's team trained AI on Tokyo address schemes, optimal routes, package sorting, and parking locations, then gave drivers their entire day optimized on their phones. Result: drivers went home on time, Amazon reduced costs, customers received packages reliably, and the company created tens of thousands of new jobs because AI scaled operations beyond human ability alone.

The principle: Don't adapt AI to old processes—reinvent processes with AI at the center.

The Agent Economy

General Purpose vs. Specialty Agents

Trent distinguished between two types of AI agents:

General Purpose Agents (ChatGPT, Microsoft Copilot): Like Swiss Army knives—versatile tools that give humans superpowers to do more in current roles. Microsoft is renaming Office to "Microsoft Copilot," and Satya Nadella says there's no need to use Excel anymore.

Specialty Agents: Like power tools—designed for specific tasks with access to company data and processes. They execute standard workflows at scale, semi-autonomously. Examples for Encore could include event planning agents, venue logistics agents, partner coordination agents, or post-event agents.

Agent-Based Prospecting and Sales

Trent outlined how AI is reinventing the sales process through agents:

  • Prospecting Agent: Trained on ideal customer profiles and discovery methods
  • Qualifier Agent: Evaluates prospects against criteria (venue size, budget, timing)
  • Research Agent: Analyzes public data (earnings statements, LinkedIn profiles, recent posts)
  • Strategy Generation: Creates hyper-personalized sales approaches matching company offerings to specific prospect needs

Sales personnel arrive to qualified prospects with ready-to-deploy, customized strategies—fundamentally shifting their role from research and qualification to closing and agent management.

Agent-to-Agent Commerce

The future of B2B purchasing: A customer's general purpose AI agent requests a three-day leadership conference for 800 attendees on specific dates. It contacts your sales AI agent, which responds with venue options, reliability ratings, and availability—completing simpler transactions autonomously while keeping humans in the loop for complex decisions.

Timeline: Agent-to-agent commerce is already happening on the consumer side and will arrive for simpler B2B transactions within six months. Organizations not preparing for this aren't preparing for the future of commerce.

Revisiting Customer Values for the Event Industry

Trent analyzed how AI transforms traditional customer expectations in Encore's industry:

  • From: Manually finding venues → To: AI venue selection agents available 24/7
  • From: Buying services piece-by-piece → To: Ready-to-run event configuration agents offering proven setup packages
  • From: Reactive emergency management → To: AI event risk mitigation agents proactively identifying and solving problems

What's Left for Humans? Vision.

When intelligence isn't your limit anymore, imagination is. The new job for leaders at every level is creating vision to serve future customers better, aligning organizations toward it, and bringing everyone along. Since AI applies to every process, competitive edge comes from people closest to the work—those working with customers and seeing problems firsthand.

The shift: In the future, the smartest people won't be those who know the most, but those who know how to think and innovate with AI.

The AI SPRINT Framework

Trent introduced a six-step framework for organizational AI transformation, emphasizing that companies should focus on the first four steps before advancing to the more complex final stages:

S - Spark Action with Leader Education

The spark—the person who says "I've got it, I like it, I want this task"—creates initial momentum. But sparks can't turn into fires without leadership to catch them. Most leadership teams aren't aligned on AI impact, investment, vision, responsibility, or employee messaging—meaning they're guessing about the future in different directions.

Three essential steps:

  1. Educate leaders on AI fundamentals
  2. Assign a transformation owner (broader than IT)
  3. Start transformation sprints with executives
P - Position Company to Win with AI

Design your company for future AI-enabled customers by answering the five Future Customer Framework questions. Leading companies don't ask "How do we save 5% in this process?" but rather "How do we reinvent to win the next phase of our industry?"

R - Rally Employees to Use AI Daily

You can't force AI adoption or create innovation through fear. Instead, create an environment where AI use is normal, expected, supported, and safe. Encore is already making progress with Microsoft 365 launching in Encore University on February 9th.

Three components:

  1. Create safety and guardrails (data protection and job security)
  2. Equip and train everyone for their specific roles
  3. Incentivize smart usage
I - Integrate AI into Sales and Marketing Processes

With over 40,000 AI tools on the market and thousands of organizational processes, where do you start? Focus on highest ROI areas:

  • Marketing content and personalization: 400% return when using AI effectively
  • Sales scoring and personalization: Not spam, but genuinely customized approaches based on prospect research
  • Operational bottlenecks: Organizations can only move at the speed of their slowest part

Encore win: The recruiting team implemented Paradox interview agents, cutting time-to-fill by addressing the coordination bottleneck.

N - eNable a Culture of Innovation

Every CEO wants a culture of innovation, but few achieve it. The secret: Giving employees AI provides 100% improvement in innovation ability even without training—if you give them access and set the expectation they'll use it for innovation.

Combined with the sprint methodology (continual rhythm of learning, experimentation, and sharing every month), organizations can build their first true culture of innovation.

Three requirements:

  1. Set clear innovation expectations
  2. Reward innovation efforts
  3. Create an idea pipeline where employees know where to send ideas for support
T - Trailblaze with New Offerings

After completing the first five steps, organizations have clear vision, aligned leadership, engaged employees, integrated AI processes, and innovation culture—firing on all cylinders. This final step reinvests that momentum into brand new products and services that weren't previously possible.

Example opportunities for Encore:

  • Guaranteed Execution Events: Sell reliability guarantees based on AI configuration knowledge
  • Global Event Operating System: Let clients plan events in your system, accessing unprecedented planning power
  • Encore Personalize: Create AI agents for every event attendee, helping with travel, networking, dining, and post-event follow-up

The AI Sprint Methodology

The most effective approach isn't one big agent project—it's building a rhythm of AI use and experimentation. At the start of every month, teams at every organizational level ask: "What's our best opportunity to use AI right now?" They try it, take a step, reflect at month's end on what they learned, adjust course, and take another step. February, March, April—continuous progress at every level.

Critical caveat: Speed without direction leads nowhere. Organizations must first build vision for their future customer so everyone moves toward the same goal.

Action Items

  1. Identify who the "spark" is on your team—or become that person
  2. Begin daily AI usage to achieve the 20% productivity improvement
  3. Rally your teams to use AI and begin creating momentum
  4. Start answering the five Future Customer Framework questions for your function

Closing: Your Day One

Amazon's "Day One" philosophy means starting every day in business as if it were your first—with the same hunger to make a difference, passion to solve customer problems, and courage to take risks. That mindset changes not just futures, but the world.

Trent's challenge to Encore: Today is your Day One to use AI—not just to write emails, but to spark new ideas, reinvent processes, create new products and services, reinvent your industry, serve future customers better, and create opportunities for everyone. You have the best tools humans have ever invented. Today, you have the moment.

Why this matters for Encore specifically: No other company has the same impact on human connection. Encore brings people together for experiences, joy, and innovation. Anything you can do with AI to facilitate that mission is improving how humans connect—a massive opportunity in an AI-enabled world where human connection becomes more valuable, not less.