Trent Gillespie, founder and CEO of Stellis AI and one of a small number of AI keynote speakers with direct enterprise AI operating experience, is expanding Operational AI keynote partnerships across association and SMB conference markets in the United States. Gillespie's flagship session "Now or Never: Turning AI into a Competitive Advantage" was delivered to an estimated 6,000 senior leaders across three national association conferences in April 2026 alone - spanning credit unions, real estate, and mental wellness - earning consistent ratings of 4.8 to 4.9 out of 5 from rooms in which roughly 80 percent of titled respondents held C-suite or President-level positions.
Operational AI category defined and trademarked by Gillespie focuses on process redesign, governance, workforce readiness, and cultural conditions.
Before founding Stellis AI, Gillespie spent nearly a decade at Amazon leading global expansion, building innovation operating model for Last Mile delivery, and defining global privacy standards for Amazon Alexa.
Forgoing approximately $1M in unvested equity to found Stellis AI in 2021.
Proprietary frameworks: AI SPRINT (transformation project plan with operational cadence) and Future Customer (AI vision setting).
Selected to train ~250 association executives at ASAE in August 2026.
Stellis AI is an OpenAI SMB Channel Partner.
Before founding Stellis AI, Gillespie spent nearly a decade at Amazon leading global expansion across every business and geography, building the innovation operating model for Amazon's Last Mile delivery network as the company began running its own logistics infrastructure, and defining the global privacy operating standards for Amazon Alexa. That arc - three nascent AI-enabled functions built at scale inside one of the world's most operationally demanding companies - is the experience base Gillespie brings to every keynote and client engagement.
Gillespie departed Amazon in 2021, forgoing approximately one million dollars in unvested equity, to found Stellis AI with a specific mission: bringing the operational AI principles powering the world's largest technology companies to the small and mid-sized businesses and associations that have never had access to them - democratizing the methods that have driven the most significant technological transformation in a generation.
Two proprietary frameworks anchor the programming. AI SPRINT combines a transformation project plan with an ongoing operational cadence - giving organizations both the roadmap to start and the rhythm to sustain AI adoption. Future Customer, inspired by Amazon, helps leadership teams set a coherent AI vision before they begin building. Both were developed through Gillespie's direct implementation work with clients across industries and are presented inside the keynote.
At the National Association of Credit Union Service Organizations (NACUSO 2026), a room in which 81 percent of titled respondents held C-suite or President-level positions rated the session 4.9 out of 5 on enjoyment, actionability, and value, with 91 percent giving the session 5 out of 5 across all three dimensions.
"Best discussion on introducing AI to an organization that I've seen out of many," said Doug Wright, CEO. "Most impressive session I've attended at any conference," said Lon Varns, President of Aries Fraud Solutions. "Best keynote I've ever heard," said Jack Antonini.
At the California Association of Realtors SPF Forum, audiences returned a 4.9 out of 5 rating. At NatCon 2026, the National Council on Mental Wellness, the keynote earned a 4.8 out of 5 rating across all three dimensions, with 79 percent of titled respondents in senior leadership roles.
"Best session I attended at the entire NatCon - feel less scared, more inspired," said Shelley Batch, Vice President of Behavioral Health. "It was motivational and actionable. Most try to hype you up but don't give you actionable steps," said Michael Jackson, SVP and Chief Innovation Officer.
In August 2026, Gillespie has been selected to deliver AI strategy training to approximately 250 association executives at the American Society of Association Executives (ASAE), focused on building industry-specific AI strategy for their member organizations. The engagement reflects a growing pattern: associations are identifying Gillespie as the practitioner-level AI resource for their industries, not simply a conference keynote slot. Additional association partnerships are in development across the United States and Canada.
"Most organizations are experimenting with AI tools, but very few have redesigned how the work itself gets done - and that is where the real return lives. Every keynote is built around the same objective: leaders leave with a clear, practical operating path they can act on this quarter, and the conviction that AI, implemented the right way, should be creating jobs in their organizations and communities, not eliminating them," said Gillespie.
Operational AI - redesigning processes, governance, and workforce roles for AI-enabled work
AI SPRINT - a repeatable cadence and transformation project plan for identifying, prioritizing, and shipping AI use cases
Future Customer - setting AI vision before building
AI agents and workflow automation across operations and customer experience
Workforce readiness and change management for sustained AI adoption
Association-specific AI strategy and member enablement
SMB AI implementation drawing on Stellis AI's engagements as an OpenAI SMB Channel Partner
Associations, SMB conference organizers, and executive teams can explore Operational AI keynote programming and recent audience feedback at TrentGillespie.live and learn more about Stellis AI's advisory and implementation work. Speaking inquiries are handled exclusively by Michelle Joyce Speakers.
About Stellis AI
Stellis AI is a Seattle-based Operational AI advisory and implementation firm serving associations, small and mid-sized businesses, and executive teams across the United States. Founded in 2022 by Trent Gillespie, a former Amazon executive with more than three decades in technology leadership, Stellis AI is an OpenAI SMB Channel Partner and works across ChatGPT, Claude, Microsoft Copilot, AI agents, and workflow automation.
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