Caleb Gardner
Keynote Speaker, Strategy Consultant, and Author
20+ years helping leaders close the gap between the ambition of new technology, human potential, and how both work together to make change.
Caleb’s Journey
I made my first website at 15, on my family’s Packard Bell, and started teaching the neighborhood kids how to use the internet. That was when my obsession with how technology changes us started.
My entire career I’ve worked at the intersection of technology strategy and human behavior inside organizations: from large firms like Edelman and Bain & Company, to startups and nonprofits, to leading digital media, technology, and data analytics for President Barack Obama.
Each role gave me a different view of the same problem: organizations get excited about the potential of new technology, but mostly underinvest in the strategy, processes, and culture that determine whether it works.
Companies don’t change; people do. And I co-founded 18 Coffees with the belief—based on experience—that the most innovative new technologies never work without bringing people along.
For the past 10+ years, my team and I have consulted with organizations like Bose, Crowe Global, and United Way Worldwide on digital transformation, AI strategy, and change management, helping to close the gap between new technology and the people expected to use it.
I also teach in Loyola University Chicago's Baumhart Scholars MBA program, and serve as a faculty affiliate in the Lab for Applied AI. The academic work keeps our frameworks grounded in research; our client work tests them against reality.
Today I spend most of my time on stages and in rooms with leadership teams, working through what it actually looks like to help organizations move faster without leaving anyone behind. The question has gotten more urgent with how AI is changing all of our work, but the underlying idea is the same: help leaders see how the whole system needs to work together—not just the shiny new part of it.
Key Milestones & Experience
2010 — Present
Keynote Speaker & Facilitator
- •100+ keynotes across 20+ industries and 3 continents
- •20,000+ leaders reached from Fortune 500 to fast-growing startups
- •Featured on global stages like SXSW, Social Innovation Summit, INBOUND, and MaxiMedia
2009 — Present
Fortune 500 Strategy Consultant
- •15+ years consulting with Fortune 500 companies
- •Led digital transformation initiatives at Edelman, Bain & Company, and now at 18 Coffees
- •Developed AI integration frameworks and operating models
2013 — 2016
OFA (BarackObama.com) Digital Strategy Director
- •Led technology, data analytics, and digital media for President Obama’s political advocacy group
- •Raised $50 million online through email and social media campaigns
- •Grew the @BarackObama Twitter account to the most followed in the world
2014 — Present
Adjunct Professor
- •Adjunct professor of management in Loyola University Chicago's Baumhart Scholars MBA program
- •Taught strategy, marketing, HR, and change management for 10+ years
- •Faculty affiliate in Loyola’s Lab for Applied AI
Areas of Expertise
Sociotechnical Systems
How technology and human behavior shape each other inside organizations. Understanding and optimizing both systems is what separates a successful transformation from a failed one.
Change Management
Building the organizational capacity for continuous change, not just surviving one initiative at a time.
Strategic Communications
From political campaigns to Fortune 500 brands to employee engagement, communications has been at the center of my work.
Radically Human Leadership Philosophy
I believe the best leaders aren’t the ones with the clearest plan.
Most leadership guidance assume a fixed destination: set the vision, execute the plan, arrive at the outcome. But the leaders I work with are operating in environments where the destination keeps moving, and the people doing the work are changing along with it. They’re the ones learning how to keep an organization moving when certainty isn’t available.
The best leaders I’ve worked with treat ambiguity as the operating environment, uncertainty as the water they swim in. They build psychologically safe teams that learn and adapt continuously, and aren’t afraid to admit when something fails. They understand that every change you ask of an organization is ultimately a change you’re asking of people.
That’s what “radically human leadership” means. As AI takes on more of the analytical and operational work, the capabilities that matter most for leaders are more human, not less: judgment, empathy, trust-building, and the ability to hold people together through continuous change.
In the human-AI workforce of the future, building AI capability will create enormous opportunity for new areas of value—but investing in human potential will be the real competitive advantage.
Frequently Asked Questions
Learn more about Caleb's background and thought leadership
Caleb Gardner is a keynote speaker, strategy consultant, and author specializing in AI strategy, change management, and leadership development. His 20+ year career spans digital strategy consulting at Edelman and Bain & Company, directing digital media and data analytics for President Barack Obama, and co-founding the strategy consulting and training firm 18 Coffees. He is an adjunct professor at Loyola University Chicago, and a faculty affiliate in the university's Lab for Applied AI. He’s the author of the book No Point B: Rules for Leading Change in the New Hyper-Connected, Radically Conscious Economy, which explores leadership and change management in conditions of uncertainty.
Caleb Gardner has delivered keynotes and consulting engagements across 20+ industries including technology, healthcare, financial services, manufacturing, professional services, higher education, philanthropy, government, media, consumer goods, and startups. Clients range from Fortune 500 companies to fast-growing startups to nonprofits.
Every engagement is customized for the specific audience and industry context.
Caleb Gardner’s keynotes are research-backed, customized, and built around practical leadership frameworks that audiences can apply immediately. He conducts pre-event research with every client organization, and builds a custom companion app for each keynote, so attendees leave with tools they can use that afternoon.
His academic work at Loyola’s Lab for Applied AI keeps the content grounded in current research; his consulting work keeps it grounded in reality.
Yes! Through 18 Coffees, Caleb Gardner and his team offer AI consulting, strategic communications, change management consulting, and leadership development programs. Engagements range from executive coaching and leadership workshops, to full strategy consulting and implementation programs. Every project starts with a conversation about what your organization actually needs.
18 Coffees is a Chicago-based strategy consulting and training firm co-founded by Caleb Gardner. The firm works with organizations on AI strategy, digital transformation, change management, and leadership development. Clients include Bose, Crowe Global, United Way Worldwide, and others across 20+ industries.
For keynote speaking inquiries about Caleb Gardner, visit the speaking page.
For consulting engagements, media requests, or other inquiries, visit the contact page.
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