Regan and Jon Judah, SVP, Clients & Technology for the Americas at DEPT, dive into how boldness is a mindset (and not just a moment), and why it’s a strategic imperative for future-ready companies. They explore why good strategies are about seeing around corners before everyone else, and how challenging the non-negotiables requires a mix of empathy, shifting a company’s culture, embracing experimentation and reevaluating what’s being held as truly core to the brand.
Key Takeaways
How bold strategies begin by working backwards from a confident hypothesis.
The importance of team psychological safety when challenging the non-negotiables.
Why questions like “what if you killed the thing that made you famous” create new opportunities for growth.
How embracing a diverse team with weird side hustles, normalizing failure and having actionable tools are key to fostering a culture of experimentation.
Why Eli Lilly’s “failure parties” help prevent future failures.
Resources
Connect with Jon on LinkedIn: https://www.linkedin.com/in/jonjudah/
Learn about Jon’s company, DEPT: https://www.deptagency.com/
About Our Guest
For over 20 years, Jon has worked at the intersection of technology, business and design to help leaders at some of the world's biggest brands define how their products and experiences can drive growth in a digital economy. As Senior Vice President at DEPT, a global full-service digital agency at the intersection of tech and marketing, Jon leads the Americas technology market and is responsible for driving growth and outcomes for over 50 clients spanning commercial and nonprofit sectors. Past clients have included The Home Depot, Mattel, Lyft, Epic Games, and Sotheby’s International Realty. He's also worked with mission-based clients including Medicare and the US State Department.
Prior to his role at DEPT, Jon served as Chief Strategy Officer at Huge, where he led a multidisciplinary team spanning data science, analytics, client partnership and strategy. Jon has authored papers on governance and technology strategy, and facilitated talks at SXSW, Cannes International Festival of Creativity, and TED. Jon also teaches a master's course on digital strategy at Georgetown University, where he was awarded the Tropaia award for outstanding faculty. Jon lives in Arlington VA, with his wife, three teenage sons and their basset hound Kingston.
About Future Fit™ with Regan Robinson
Future Fit™ unravels the secrets of how the world’s most innovative leaders stay future-ready in a fast-paced world. Hosted by futurist and strategist Regan Robinson, each episode explores how trailblazing executives turn uncertainty into their strategic advantage. Gain powerful insights and practical approaches as these visionary minds share the unconventional and imaginative ways they thrive today while leading their teams into tomorrow.
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About Regan Robinson
Regan Robinson is a holistic futurist and business strategist that empowers visionary companies to turn uncertainty into advantage and effortlessly innovate and strategize for their future. Over the course of 20+ years, she has helped some of the world’s most influential brands and companies strategize and grow. Regan has spearheaded revenue increases of 300%+, led as an executive at 3 start-ups and established business models, new capabilities, infrastructure and roadmaps for companies like VICE Media and Edelman Digital.
Website: https://www.reganrobinson.com/
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