The Rethinking Work Show

Is career success measured by moving up or moving forward? Cliff Maxwell, co-founder and CEO of Vocation, explores the difference between career progression and career progress, why fulfillment matters as much as advancement, and how individuals can take greater ownership of designing meaningful careers in a rapidly changing world of work. Cliff Maxwell is the Co-founder and CEO of Vocation, an AI...

What happens when you leave the career you've spent decades building? Julie Fedele, a Future of Work strategist and portfolio career mentor, explores why career transitions are as much about identity as opportunity, and how more professionals are moving beyond traditional employment to build a body of work that’s truly their own. Julie Fedele is a Future of Work strategist and portfolio career men...

In a world overflowing with productivity tools and AI assistants, are we actually working better together? Toby Daniels, co-founder of ON_Discourse and Domain, explores why the future of work depends on better collaboration, stronger networks, and systems that help us think and not just work more effectively. Toby is the Co-Founder of ON_Discourse , a global network of technology, business and inn...

As AI transforms marketing and reshapes organizations, what skills and leadership qualities will matter most? Richard Sanderson, Partner at Spencer Stuart, explores how companies are rethinking talent, adapting team structures, and balancing automation with human judgment. Richard Sanderson is a Chicago‑based Partner and Consultant at Spencer Stuart, where he advises CEOs, boards, and people leade...

What if teams weren’t built around roles, but around problems? Britt Gage, founder and CEO of oAT (of All Trades), explores the shift from static org charts to dynamic teaming, where generalist operators execute, adapt, and connect across functions. As AI reshapes work, Britt argues the future belongs to flexible, problem-centered teams, and to organizations designed to move as fast as the challen...

In a world where skills expire faster than ever, how do you stay relevant? Veronika Kryuchkova explores the idea of the “capability stack", a dynamic mix of core, human, and future skills, and why thriving in today’s workplace requires continuous reinvention, high agency, and the ability to learn, unlearn, and evolve faster than the market. Veronika Kryuchkova is the Global Head of Capability Buil...

What if we stopped paying for time and started paying for outcomes? Matt Seiler, founder and CEO of Excelerators Inc ., explores why traditional compensation models are breaking down in an AI-driven world, and how performance-based pay, better incentives, and a renewed focus on human value can reshape how we work, measure success, and reward impact. Matt Seiler is the founder and CEO of Excelerato...

As AI accelerates and traditional corporate structures strain under pressure, what does leadership look like in the next era of work? Justin Billingsley, co-founder of Simbioniq and former Global CMO of Publicis Groupe, explores why the age of heroic managers is giving way to orchestrators who design systems that think, adapt, and coordinate at scale.  Justin Billingsley is Co-Founder of Simbioniq...

Are we preparing students for the world of work or a world that no longer exists? Authors Alexandra Levit and Stephanie Loeck explore how work-based learning can close the gap between education and employment, and why real-world experience, not just classroom instruction, may be the key to building adaptable, future-ready talent. Purchase and learn more about their book Make School Work here: http...

What if the future of careers isn’t about résumés or job titles but about fit? Avi Steinlauf and Tomas Chamorro-Premuzic, co-founders of myTrudy , explore how personality science and AI are reshaping career decisions, helping people move from static search to dynamic, human-centered reinvention in a rapidly changing world of work. Avi Steinlauf is the CEO and Co-Founder of myTrudy, a personality-d...

As AI reshapes the marketing landscape, what makes human talent more essential not less? Jeff Levick, CEO of We Are Rosie, shares why performance-based compensation, flexible teams, and the right culture are key to unlocking the full power of people in a tech-driven world. Jeff Levick is a 20+ year veteran leading media, marketing, and digital growth companies from early stage through IPO. Current...

How do we bring dignity, flexibility, and innovation to the millions of hourly workers who keep our world running? Jarah Euston, President and Co-founder of WorkWhile, shares how behavioral data and community-driven design can reshape frontline work and why the future of labor starts on the warehouse floor. Jarah Euston is the President and Co-founder of WorkWhile, a workforce-as-a-service platfor...

How can small teams now match, and even outperform, the output of much larger organizations? The team at Fourth Wall Advisors shares how AI-driven workflows, intentional design, and diverse, non-overlapping expertise are reshaping how work gets done. From reducing friction to unlocking deeper creativity and faster iteration, they explore why the future of high performance belongs to small teams bu...

What if where people live became a core part of how they work? Gary Brown, president and co-founder of Furnished Quarters, shares how workforce mobility is changing in a hybrid world, and why companies are shifting from hotels to flexible housing, what employees need to thrive on remote assignments, and how thoughtful living solutions can strengthen culture, retention, and performance. As Co-Found...

What if companies could access top creative and marketing talent as easily as opening an app? Lara Vandenberg, founder and CEO of Publicist, shares how she built a platform that connects global brands with premium freelance talent, and why the future of work depends on flexible, trusted systems that empower both companies and creators. Lara Vandenberg is the founder and CEO of Publicist , a freela...

What if the corporate job is no longer the default path to a meaningful career? Alex McCann, founder of TrueNorth, explains why so many young professionals feel lost at work, how Gen Z is redefining success, and why the future may belong to those who start with self-discovery instead of job titles. Alex McCann is a writer, community builder, and founder of TrueNorth , an AI-powered career coach de...

What if culture was the key to competitive advantage? Alastair Creamer and Doug Milliken, co-founders of Creamer Milliken, share why accelerating culture change is essential for growth, how leaders can make transformation stick, and why the companies that thrive tomorrow will be the ones that reinvent from the inside out. Alastair Creamer is a cultural change consultant and co-founder of Creamer M...

What happens when AI rewires the workflows of modern finance? Bin Ren, founder and CEO of SigTech, explains how artificial intelligence is transforming how financial institutions design, test, and execute investment strategies, and why the future of finance depends on smarter, faster, and more adaptive ways of working. Before founding SigTech at the start of 2019, Ren was the Chief Investment Offi...

What if the most important approval you’ll ever need is your own? Author and coach Jillian Reilly discusses her book The Ten Permissions, and why we struggle to let go of others’ expectations, and how to start giving ourselves permission to live and work on our own terms. Jillian Reilly is a founder, author, and keynote speaker. Having spent her 30-year career working in social, organizational, an...

How is AI reshaping who holds power in the knowledge economy? Sangeet Paul Choudary, the best-selling author of Platform Revolution and Reshuffle explains how artificial intelligence is re-stacking the way knowledge is created, distributed, and monetized, and what this means for workers, companies, and the future of competitive advantage. Sangeet Paul Choudary is the best-selling co-author of Plat...

What if the key to the future of work isn’t jobs themselves, but the skills that unlock them? David Timis, Global Communications & Public Affairs Manager at Generation, shares why building adaptable skills is more important than chasing job titles and how organizations like Generation are helping people prepare for meaningful, resilient careers in a changing world. David Timis  is a Global Communi...

What happens when work stops being about full-time jobs and starts being about outcomes? Paul Suchman, Freddie Laker, and Juan-Carlos Morales of Chameleon Collective share how the rise of fractional leadership is reshaping companies, giving professionals more flexibility, and challenging traditional ideas of careers, culture, and collaboration. Freddie Laker is a serial entrepreneur, growth strate...

How do you spot and grow the kind of leaders who can thrive in the age of AI? Jay Haines, co-founder and global president of Grace Blue, shares how expectations for leadership are shifting, what skills will define success in an AI-driven world, and why human potential still matters most.   EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional musi...

What if you could tap into top talent, anywhere in the world, exactly when you need it? Luke Smith, CEO and co-founder of Croud, unpacks how the “talent on demand” model is reshaping teams and blending speed, scale, and flexibility without sacrificing culture or creativity. Luke Smith  is the Global CEO and co-founder of Croud, a leading independent digital agency. Since 2011, Luke has helped grow...

What if being a company of one wasn’t just a structure, but a strategy? Flavia Barbat, editor-in-chief of Brandingmag, shares how professionals can build careers around clarity, substance, and intention in a world where content is everywhere but meaning is rare. As founder of Brandium, Inc. and Editor-in-Chief of Brandingmag , Flavia has been responsible for nurturing and promoting the creation of...