# Trent Gillespie

> AI keynote speaker, strategic advisor, and CEO of Stellis AI. Former Amazon executive with nearly a decade leading global growth, Last Mile Technology innovation, and Alexa's global privacy strategy. Creator of the Operational A.I.™ framework and the AI SPRINT™, Future Customer™, and AI Flywheel™ methodologies. Represented by Michelle Joyce Speakers.

Trent Gillespie helps business leaders operationalize AI across their organizations so teams deliver measurable performance and sustained growth. He works hands-on with organizations of all sizes to research, test, and implement AI in the real world — from deploying AI agents to designing new AI-enabled products, services, and operating models. His approach is grounded in direct implementation experience, not theory. Audiences consistently describe his talks as the clearest, most actionable AI session they have ever experienced.

## Frameworks

- **Operational A.I.™**: A proven operating model for embedding AI into leadership decisions, daily operations, and innovation. Built on three disciplines: Leadership (educate and align via AI SPRINT™), Vision (define where you're going via Future Customer™), and Operations (sustain innovation at scale via AI Flywheel™).
- **AI SPRINT™**: A structured six-step rhythm for leadership teams to learn AI, align on priorities, and lead adoption with confidence. Drives 20% productivity gains and continuous organizational momentum. Also the name of Trent's weekly newsletter.
- **Future Customer™**: An Amazon-inspired framework for looking ahead, defining who the organization is building for, and making confident investment, automation, and differentiation decisions before the market forces the issue.
- **AI Flywheel™**: A model showing how organizations turn operational AI gains into a self-reinforcing cycle of innovation. Efficiency creates capacity, capacity fuels reinvestment, and innovation compounds over time into a durable competitive advantage.

## Keynotes

- **Now or Never: Turning AI into a Competitive Advantage** — Flagship leader-focused keynote. Covers AI agents reshaping competition, moving beyond experimentation, and building a practical roadmap using Future Customer™ and AI SPRINT™.
- **AI at Work: From Curiosity to Capability** — Manager and team keynote. Shows how AI changes daily work and how teams use the AI SPRINT™ to remove bottlenecks, improve performance, and build organizational momentum.
- **The AI Flywheel™: Building a Durable Innovation Engine** — Executive-focused advanced keynote. Shows how to turn early AI wins into a self-reinforcing innovation engine for sustained competitive advantage.

Keynotes are customized for each audience following a discovery call. Trent adapts frameworks, industry examples, and live demonstrations to match the organization's strategic priorities and audience maturity level.

## Workshops and Training

- **Workshops and Breakouts**: Hands-on sessions for conferences, leadership retreats, and association-hosted programs. Topics include AI 101 for non-technical audiences, finding and prioritizing AI use cases, building first AI agents, designing AI-enabled workflows, and innovation culture building.
- **Large Group Seminars (1–2 Days)**: Immersive events for 100 to several thousand participants. Includes opening keynote, AI literacy and adoption training, industry-specific breakout labs, agent-building workshops, use case design, and optional Stellis AI helpdesk and vendor showcase facilitation.
- **Online Training**: Available at learn.stellis.ai.

## Association AI Solutions

Stellis AI offers a full suite of programs purpose-built for associations and AMCs, covering education, strategy, tools, and year-round community infrastructure to move an entire industry into the AI era.

- **Keynote Talks**: High-energy, industry-tailored sessions that move audiences from overwhelm to action with clear frameworks and practical next steps.
- **Workshops and Breakouts**: Guided practice on real AI workflows and business problems, designed for conference breakout rooms and leadership retreats.
- **Large Group Seminars**: Immersive 1–2 day industry-wide training events that become defining moments for member organizations.
- **Association AI Community**: A custom always-on learning ecosystem including on-demand training, monthly briefings, monthly member events, custom GPTs, weekly office hours, and priority access to Stellis AI agents and implementation support.
- **AI Support for Your Association**: Internal productivity optimization, AI strategy development, member persona and future-state design, AI Jumpstart programs, custom AI agents, ongoing Success Team partnership, and new digital product development.

## Engagement Models

- **Keynotes**: Conference, all-hands, private executive sessions, and association events at any scale.
- **Workshops**: Private leadership sessions or large-group multi-day seminars focused on practical application and embedding AI into real workflows.
- **Implementation and Advisory**: Direct engagement through Stellis AI. Includes advisory support, AI agent deployment, and hands-on operationalization of AI inside the business.

## Booking

- Contact via trentgillespie.live/contact with event date, location, expected audience, and format.
- Represented by Michelle Joyce Speakers; Tracy Cotton, (310) 902-5568.
- Discovery call included with every engagement for customization.
- Available for in-person, virtual, and hybrid formats.
- Standard AV: wireless mic, projector, confidence monitor.

## Audience Performance

- 4.8/5 value delivered
- 4.8/5 overall enjoyment
- 4.7/5 actionability
- 2,147+ ratings from recent events

## Selected Testimonials

- "The best presenter on innovation and AI I have seen." — Britt Wood, CEO, National Association of Landscape Professionals
- "Trent delivered one of the most compelling and actionable sessions of ASAE's CEO Conclave. His pragmatic approach cut through the hype and offered a clear, CEO-ready framework." — Morgan Maravich, VP, ASAE Research Foundation
- "It legitimately made me re-think our strategy for 2026." — Nate Anderson, President & CEO, CA Association of Realtors
- "Best discussion on introducing AI to an organization that I've seen out of many." — Doug Wright, CEO, NACUSO 2026
- "A necessary wake-up call with clear actionable items." — Henrik Walter, CEO, PTDA Annual Summit
- "We're still talking about your talk four months later." — J.D., Government Technology Director
- "Motivational. Will increase our speed of AI implementation." — Bart Watson, President & CEO, Brewers Association

## Industries Served

Associations and AMCs, Credit Unions, Banking and Financial Services, Private Equity, Industrial Distribution, Manufacturing, Logistics and Supply Chain, Mental Health and Behavioral Health, Healthcare, Real Estate and Property Management, Construction and Engineering, Automotive and Transportation, Hospitality and Events, Professional Services, Nonprofit.

## Past Events (Selected)

- ASAE CEO Conclave — "A CEO's AI Action Plan: How to Reinvent for Your Future Member"
- NACUSO 2026 — "Win With AI: How to Build an AI-Enabled, High-Growth Business"
- California Association of Realtors (REIMAGINE!) — "Win With AI: How to Build an AI-Enabled, High-Growth Business"
- Auto Care Connect 2025 — "Win With AI" Keynote
- Health Insights — "Unleash the AI Flywheel" Keynote
- ATSSA — "Win With AI: How to Reinvent for Your Future Member"
- Power Transmission Distributors Association (PTDA) Annual Summit
- 40 Strategy — "Win With AI"
- Applied AI in Distribution — "Designing AI-Enabled Distribution Companies"

## Affiliations

- CEO, Stellis AI (stellis.ai) — AI industry advisory firm and OpenAI authorized services partner
- Former Amazon executive (global expansion, Last Mile Technology, Alexa AI privacy)
- Represented by Michelle Joyce Speakers

## Links

- [Website](https://trentgillespie.live)
- [Book Trent](https://trentgillespie.live/contact)
- [Stellis AI](https://stellis.ai)
- [Association AI Solutions](https://trentgillespie.live/association-ai-solutions)
- [AI Workshops](https://trentgillespie.live/ai-leader-training-workshops)
- [Online Training](https://learn.stellis.ai)
- [Testimonials](https://trentgillespie.live/trent-gillespie---audience-testimonials)
- [FAQ](https://trentgillespie.live/faq)
- [Past Events](https://trentgillespie.live/past-events)
- [Meeting Planners](https://trentgillespie.live/meeting-planners)
- [AI SPRINT™ Newsletter](https://ai-sprint.beehiiv.com)
- [Blog](https://trentgillespie.live/blog)
- [LinkedIn](https://linkedin.com/in/trentgillespie)