The Rethinking Work Show

Rishad Tobaccowala

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.

  1. Dynamic Teaming

    5D AGO

    Dynamic Teaming

    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 founder and CEO of oAT (of All Trades), a company reimagining how teams are built in the age of AI. Drawing on 15+ years in early-stage startup operations across talent, growth and people functions, Britt launched oAT to offer organizations an alternative to rigid, specialist-driven hiring models. of All Trades (oAT) is built around a different kind of operator, embedded generalists who flex around problems rather than job descriptions. Over the past five years, oAT has grown from a solo practice to serving 50+ organizations from startups to nonprofits. At the core of their work is a proprietary Dynamic Teaming methodology, where teams form around problems and disband when problems change, where skills matter more than titles, and where generalists become the essential connective tissue holding it all together.  EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past.  This show is also available on YouTube which includes visual supplements.  Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.

    32 min
  2. The Capability Stack

    APR 16

    The Capability Stack

    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 Academy, where she leads initiatives to equip teams with the skills and mindsets needed to drive transformation at scale. The Academy reaches 90% of Reckitt’s marketers across 59 countries and has been recognized externally with the prestigious Learning Technologies Award for its impact. Her work focuses on how individuals and organizations build the capabilities required to adapt in a rapidly changing world, with a particular emphasis on continuous learning, reinvention, and high-agency performance. Beyond her corporate role, Veronika hosts the podcast Get Superpowered, where she explores the human side of transformation, including creativity, connection, and courage. Through her work, she champions the idea that thriving in the future of work requires not just new skills, but a new approach to growth—one rooted in curiosity, adaptability, and intentional development. EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past.  This show is also available on YouTube which includes visual supplements.  Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.

    36 min
  3. Rethinking Compensation

    APR 1

    Rethinking Compensation

    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 helping organizations rethink talent, incentives, and performance in an AI-driven world. A three-time CEO in the advertising and media industry, Matt has spent more than two decades leading and transforming companies, and the last seven to eight years reimagining what effective talent management looks like today. He has played a key role in building and scaling tech-enabled marketplaces that connect people to work they are most energized to do and organizations to the talent best suited to deliver results. With Excelerators Inc., Matt is expanding that vision beyond individuals to help companies redesign how they structure teams, measure value, and reward performance. Known for his focus on performance-based compensation and the intersection of technology and human potential, Matt brings a practical and forward-looking perspective to the future of work. EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past.  This show is also available on YouTube which includes visual supplements.  Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.

    38 min
  4. The Orchestration Era

    MAR 19

    The Orchestration Era

    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 psychologically complete digital humans for marketing research, and author of "Brandflow: The Marketing Orchestration Playbook." As former Chief Marketing Officer of Publicis Groupe, including seven years on the Management Committee, Justin led marketing transformation for one of the world's largest advertising holding companies. His earlier client-side experience includes leadership roles at Coca-Cola, Nokia, Orange, and Unilever. Justin writes Brandflow, a twice-weekly strategic newsletter for senior marketing leaders navigating what he calls "The Great Compression” or the simultaneous forces of budget decline, platform disintermediation, AI automation, and margin compression reshaping the industry. His work focuses on sustainable transformation practices, moving from "sidelines to arena," and building competitive advantage through systematic orchestration rather than heroic coordination. EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past.  This show is also available on YouTube which includes visual supplements.  Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.

    39 min
  5. Work Enabling Learning

    MAR 4

    Work Enabling Learning

    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 Levit is the founder and CEO of Inspiration at Work, a futurist consulting firm dedicated to helping organizations and their employees thrive in a rapidly evolving business landscape. A former nationally syndicated columnist for The Wall Street Journal, Alexandra is the bestselling author of They Don’t Teach Corporate in College, Humanity Works, and Make School Work, which addresses the American youth employment crisis through work-based learning. She holds a certificate in strategic foresight from the University of Houston and advises leading organizations including Deloitte, American Express, Adecco, and Upwork on leadership, workforce transformation, technology adoption, and skills development. Alexandra has collaborated extensively with U.S. government agencies, including the Department of Labor and Department of Defense, and her work has been featured in outlets such as The New York Times, Forbes, CNN, and NPR. Recognized by Thinkers50 and the American Management Association, she lives in Chicago. Stephanie Loeck is Vice President of Strategic Development at GPS Education Partners, where she leads national growth initiatives advancing work-based learning and expanding career-connected opportunities for students. A passionate workforce and education advocate, Stephanie brings expertise across strategy, policy, communications, and economic development to help modernize the transition from school to work. At GPS Education Partners, she shapes long-term growth strategies, builds partnerships, and drives thought leadership around learner-centered program design. She played a key role in developing GPS Ed’s signature six-part work-based learning framework, which supports program implementation, continuous improvement, and sustainable impact. Previously, Stephanie served as Vice President of Partnerships at America Succeeds, engaging business leaders in education reform initiatives such as Durable Skills and Age of Agility. She has also worked in economic development and with technology startups. Based in Colorado, Stephanie serves on national advisory boards championing authentic, career-connected learning aligned with the future of work. EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past.  This show is also available on YouTube which includes visual supplements.  Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.

    36 min
  6. Beyond The Resume

    FEB 18

    Beyond The Resume

    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 using validated psychometrics and AI to help individuals and organizations make better, fit-first career decisions. At myTrudy, Avi is building a new category at the intersection of human potential, data platforms, and the future of work. Prior to myTrudy, Avi spent more than two decades at Edmunds, where he served as CEO and led the company through its successful sale to CarMax. Under his leadership, Edmunds scaled into one of the internet’s most trusted consumer marketplaces, known for its data-driven products, industry transparency, and market influence. Avi holds an MBA from the Kellogg School of Management and earned his undergraduate degree from Yeshiva University. Tomas Chamorro-Premuzic is the chief science officer at Russell Reynolds Associates, a professor of business psychology at University College London and at Columbia University, a cofounder of MyTrudy.com, and an associate at Harvard’s Entrepreneurial Finance Lab. He is the author of Why Do So Many Incompetent Men Become Leaders? (and How to Fix It) (Harvard Business Review Press, 2019), upon which his TED talk was based, and  I, Human: AI, Automation, and the Quest to Reclaim What Makes Us Unique, (Harvard Business Review Press, 2023). His latest book is Don’t Be Yourself: Why Authenticity Is Overrated (and What to Do Instead)(Harvard Business Review Press, 2025).         EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past.  This show is also available on YouTube which includes visual supplements.  Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.

    43 min
  7. Turbocharge Human Talent

    FEB 4

    Turbocharge Human Talent

    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 Officer at We Are Rosie, an agency that’s imagining and building a better future for the advertising industry with fractional talent and teams as well as a community-based approach. Prior to joining We Are Rosie in 2023, Levick was the COO of Redesign Health, a venture studio firm focused on the health and wellness vertical. Before that, he was the CEO of The Players’ Tribune, a new media company founded by Derek Jeter that provides athletes with a platform to connect directly with their fans, in their own words. Jeff led the company’s acquisition by Minute Media in December 2019. Jeff served as Spotify’s Chief Revenue Officer from 2011 to 2016, leading the company’s commercial business and its global acceleration from 1mm subscribers to more than 40+mm subscribers. He also grew Spotify’s physical footprint from 11 countries to over 60 markets worldwide. Prior to Spotify, Jeff served as President of Global Advertising and Strategy at AOL from 2009 – 2011 where he was responsible for the overall revenue business including premium display, Advertising.com, research, marketing, ADTECH, and branded entertainment. Before AOL, Levick held various global leadership roles at Google in the US and Europe from 2001 to 2009 where he was also an original member of its advertising team. A frequent lecturer on topics related to media, marketing and digital trends, Levick is also an Executive Director at NYU’s Entrepreneurial Institute. He holds a B.A. from New York University and a law degree from DePaul University in Chicago.  EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past.  This show is also available on YouTube which includes visual supplements.  Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.

    40 min
  8. The Shift Work Revolution

    JAN 21

    The Shift Work Revolution

    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 DataOps platform Nexla and was founder and CEO at Famous Media, a pioneer in hyperlocal content acquired by McClatchy. She also led the analytics and marketing teams at Flurry, an innovator in mobile app analytics acquired by Yahoo, where she was VP of Product. Jarah was formerly a consultant at Boston Consulting Group and started her career in hourly work as a retail associate. She is a member of EY Entrepreneurial Winning Women. Jarah holds an MBA from the Wharton School at the University of Pennsylvania and a BS from New York University. EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past.  This show is also available on YouTube which includes visual supplements.  Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.

    37 min

Ratings & Reviews

5
out of 5
6 Ratings

About

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.

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