Exclusive, Expert AI Advisory

The Luminary community is a peer group purpose-focused on helping leaders like you learn how to use AI + innovation to improve their companies, careers, and communities. With the latest expertise, weekly office hours, monthly events, and access to ongoing AI training, members have the tools they need to thrive in the AI revolution.

Leadership Community

Business leaders face a never-before-seen opportunity with generative AI, and those who can best harness it will thrive. Apply now to join the exclusive and limited leadership group, designed for scale-up and mid-market leaders to have the best information, training, advisory, and peer group to make the most of the AI revolution.

Community Benefits

The Luminary Community provides unique offerings available nowhere else

Practical Advice
No Hype. Only real, practical advice and instruction.
Peer Group
Meet leaders like you and work together to solve AI adoption and transformation challenges
Latest Research
The Luminary community prioritizes research and future training

Expert Training, Proven Results

Trent Gillespie, the Luminary founder, is a seasoned technology and business leader with a decorated career spanning over two decades. After holding various IT leadership roles, Trent spent almost nine years at Amazon orchestrating its global growth, driving massive innovation programs, and ensuring the Alexa AI met all customer privacy expectations globally.

Trent now utilizes his wealth of experience to help business leaders build innovative organizations and products and learn to harness AI for their success. Trent speaks professionally, advises, and trains leaders and their teams. Holding an MBA and a Certificate in Executive Leadership from Seattle University, Trent’s vast knowledge and experience make him an invaluable asset to any organization seeking guidance and leadership in the realm of business and technology.

Trent Gillespie
Profile image of Trent Gillespie

Not a Leader? Join Individually

Our Innovation courses include 3 months of individual-level membership, giving access to foundational resources, the newsletter, online and in-person events, and online communities. Extend the membership now by purchasing a month-to-month or annual subscription.

Embrace the AI Revolution Today

Start your journey with our meticulously designed AI-powered courses. Choose from a variety of plans each crafted to cater to your unique needs.

luminary feature image

Embrace the AI Revolution Today

Start your journey with our meticulously designed AI-powered courses. Choose from a variety of plans each crafted to cater to your unique needs.

Individual Membership

Join as an Individual member and get access to individual-level Luminary benefits and online community.
Exclusive, expert-provided online training
Weekly office hours for consultation
Luminary Newsletter
Online Community
In-Person and Online Events

Leader Membership

Join as a Leadership member and get access to all Luminary benefits and the in-person and online peer network.
$500 /mo
Exclusive, expert-provided online training
Weekly Leadership Lunch and Learns
Luminary Newsletter
Prioritize Luminary Research
In-Person and Online Events and Community


From falling behind to leading with AI - our customers are redefining their business landscapes.

“VERY informative and incredibly aligned with the way we think ...not to mention a delightful peek behind the Amazon methodology curtain."


Director, Growth and Creative Strategy, Technology Startup

"Excellent Value!"


Director, Product Management, Fortune 100 Retailer

"Fantastic, Actionable Content!"


Senior Product Manager, Fortune 100 Retailer



COO of Tech Start-Up

Join the Luminary Community

AI technologies and practices are continually changing. Join our leadership community to stay up-to-date and discover how to leverage generative AI for future career and business success.

Frequently Asked Questions

How are courses delivered?

Luminary provides courses in three formats:

Self-Paced Courses: These are online courses delivered through our online learning platform, and can be attended at any time and at the speed each student desires.

Cohort Courses: These are online courses delivered through our online learning platform, but they occur at a prescheduled time, date, and frequency for the duration of each class. Each class has a private online peer community for collaboration, both during and after the class. They average 10-15 students enrolled at the same time.

Workshops: These are typically in-person workshops (sometimes virtual), with content delivered over a condensed, 1-2 day period. Most often these are for individual companies who may want to train a peer group at the same time.

Who are the course instructors?

Each class is taught by different instructors, and the instructor is shown on the course information page. All instructors are considered experts in their fields and are drawn from organizations where they have demonstrated the practical application of these concepts at scale.

How long do I get access to courses for?

This may vary by course, but for most courses, students are provided access for the lifetime of that course on our platform. Because the course content is regularly updated, this provides significant long-term value as AI and related methods are improved.

How often are the courses updated with new content?

This varies based on each course and the pace of innovation within the subject it covers. Most courses are expected to be updated at least 2 times per year, with updates tracked within the corresponding online community in the interim.

What are the community membership levels?

Luminary is launching with two membership tiers: Individual and Leadership. These are summarized below:

Individual Tier: This membership level is for professionals who focus on executing innovation, and how to use AI to improve their individual tasks, processes, and offerings. This includes access to relevant individual training and the related online peer community.

Leadership Tier: This membership level is for leaders who have business-level responsibility, from identifying new business strategies and offerings to workforce transformation. Leaders span from start-up leaders to enterprise CxOs.