Dion Flynn
Dion Flynn helps teams break barriers and build trust fast, using improv strategies loved by Google, Maersk, and Oprah Magazine.
5.00 of 5
Top rated! Why book Dion Flynn for your next event
- With over 100 appearances on The Tonight Show Starring Jimmy Fallon, Dion Flynn brings world-class comedic timing, dynamic stage presence, and storytelling mastery to every keynote, ensuring your audience is not only captivated but also equipped with actionable communication tools drawn from the highest level of performance.
- Trusted by global industry leaders like Google, PWC, Maersk, and Ecolab, Dion Flynn has delivered high-impact workshops and keynotes that transform team dynamics, enhance interpersonal communication, and spark creative thinking across every layer of an organization, from executive boards to frontline teams.
- Recognized by Oprah Magazine as “one of our favorite creative thinkers,” Dion Flynn combines humor, emotional intelligence, and deep insight to create unforgettable keynote experiences that help teams break down barriers, foster authentic connection, and thrive in high-pressure environments.
Non-binding request for Dion Flynn
The Improvisor’s Mindset: Tools for Real-World Leadership and Growth
Elevate your event with the unmatched charisma of Tonight Show favorite and improv expert Dion Flynn. With over 100 national TV appearances and praise from Oprah Magazine as a top creative thinker, Dion delivers transformational keynotes that blend humor, storytelling, and actionable tools. Trusted by Google, Maersk, and PWC, he helps organizations break silos, spark authentic connection, and improve communication that drives measurable business results.
Keynote Speaker Dion Flynn is best known for his unforgettable impersonation of Barack Obama on The Tonight Show Starring Jimmy Fallon, where he appeared more than 100 times. But beyond the stage and screen, Dion is a master of connection, using the art of improvisation to teach organizations how to communicate, collaborate, and thrive in today’s complex work environment.
As a comedian, army veteran, teacher, and NYU-trained performer, Dion brings a unique blend of credibility, charisma, and emotional intelligence to every keynote. His signature framework, The Improvisor’s Mindset, co-created with Jeanne M. Stafford, turns improvisational theatre techniques into powerful tools for business communication, leadership, and authentic human connection.
Trusted by leading organizations like Google, PWC, Maersk, and Ecolab, Dion has helped teams across industries reduce friction, build trust, and unlock creative potential through actionable, engaging experiences. He is praised by Oprah Magazine as “one of our favorite creative thinkers” and delivers keynotes that leave audiences energized, inspired, and ready to perform.
Whether you're facing communication breakdowns, cultural disconnect, or change fatigue, Book Dion Flynn for your event to spark transformation with laughter, insight, and lasting impact. His approach is practical, entertaining, and immediately useful in today’s fast-moving business landscape.
Don’t just motivate, connect. Book Keynote Speaker Dion Flynn to make your next event truly unforgettable.
Customer Reviews
5 of 5
"One of the funniest guys I know"
Jimmy Fallon The Tonight Show
5 of 5
"Dion is extremely intuitive and is a fantastic listener. He can pull things out of you that you didn't know were there and allows you to decide for yourself what's the best.....I highly recommend him!"
Paul P. Pompeo Lumen Technology Sales
5 of 5
"One of our favorite creative thinkers"
Oprah Magazine
Rated 5.00/5 based on 3 customer reviews
Keynotes
Keynote by Dion Flynn:
Improvisors Mindset
Are your teams struggling to adapt, connect, or communicate under pressure?
The Improvisor’s Mindset with keynote speaker Dion Flynn is the transformational experience your organization needs. This full-audience improv session isn’t just fun, it’s a powerful tool for building leadership agility, boosting sales confidence, and enhancing authentic communication across every level of your business.
Drawing from over 100 Tonight Show appearances and years of work with Google, PWC, and veterans' groups, Dion guides participants through interactive exercises that break down barriers, foster trust, and spark creative thinking.
Whether you're leading through change, unifying remote teams, or empowering people in recovery, The Improvisor’s Mindset creates immediate, meaningful impact.
Book Dion Flynn for your event and give your people the skills to listen deeply, respond with clarity, and lead with confidence, in real time.
This isn’t a talk. It’s transformation in action.
Keynote by Dion Flynn:
Early, Early, Late Show
Is your leadership message falling flat or struggling to truly engage your people?
The Early, Early, Late Show flips the script on traditional corporate presentations. In this dynamic, fully customized keynote experience, Dion Flynn, best known from The Tonight Show Starring Jimmy Fallon, hosts a late-night talk show where your company leaders are the featured stars and your team becomes the live studio audience.
Blending entertainment with strategic communication, this format transforms executive messaging into an energizing, interactive experience that makes people sit up, laugh, and listen. Dion’s expert hosting and improv skills put leaders at ease while spotlighting their vision in a format your audience won’t forget.
Whether launching a new initiative, rallying teams, or celebrating success, The Early, Early, Late Show drives connection, clarity, and engagement like nothing else.
Book Dion Flynn for your event to turn top-down communication into a must-see moment. Real talk. Real results. Real fun.
Keynote by Dion Flynn:
Truth in Comedy
Is your company culture stuck in buzzwords, with little real connection or authenticity?
Truth in Comedy is a customized keynote experience by Dion Flynn that dives beneath surface-level slogans to reveal the heart of your organization, through humor, storytelling, and improvisation. With over 100 appearances on The Tonight Show Starring Jimmy Fallon, Dion brings unmatched comedic insight and emotional intelligence to your culture conversation.
By spotlighting the truths behind your culture, what’s working, what’s not, and what’s unspoken, Truth in Comedy creates a safe, engaging space where real connection can spark. It’s funny, yes, but it’s also deeply effective.
Whether your goal is to strengthen team identity, navigate change, or build authentic leadership, this keynote offers powerful clarity and levity that moves people forward.
Book Dion Flynn for your event and use comedy not just to entertain, but to transform how your culture connects, communicates, and grows.
Truth In Comedy Workshop
Watch Dion Flynn in action!
Improvisor's Mindset Sample
Watch Dion Flynn in action!
Dion Flynn Sizzle Reel
Watch Dion Flynn in action!
