Rethinking Work is a show hosted by Rishad Tobaccowala about how work is changing and how we can change with it. In each episode, Rishad sits down with bold thinkers, builders, and leaders to explore the future of work across industries. From remote work and AI to purpose, creativity, and culture, we uncover the ideas reshaping how we live, lead, and grow in today’s world. Subscribe to hear fresh, human conversations about what work can and should become.
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 challenges they face.
Britt Gage is the fo...
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 Building for the Reckitt Marketing Acad...
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 Excelerators Inc., a company focused on helpin...
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, an AI company creating psychologi...
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: https://makeschoolwork.org/
Alexandra L...
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-driven career intelligence platform us...
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. Currently, he serves as the Chief Executive...
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 platform. Previously, she co-founded the Da...
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 built for curiosity, adaptability, an...
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-Founder and President of Furnished Quarte...
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 freelance management system and premium tal...
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 designed to help people build meaningfu...
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 Milliken. He began his career at Unil...
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 Officer of the Systematic Investment Gro...
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, and individual change across Africa, A...
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 Platform Revolution and the author of Re...
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 Communications & Public Affairs Manager at G...
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 strategist, and founding partner of Chamel...
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 music licensed through Premium Beats
LINKS
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 Croud into a full-service powerhous...
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