The Meg and Amy Show
Join best friends Meg Bear and Amy Wilson on The Meg and Amy Show – a podcast for big-picture thinkers who are ready to challenge the status quo. As former tech executives and seasoned business leaders, Meg and Amy have spent decades leading through change. Now, they’re joining forces to break down the trends they’ve lived and helped shape.
Episodes
December 26, 2025 • 96 mins
Amy and Meg get brutally honest about the toxic workplace archetypes every leader faces - and share the real stories that shaped their careers. This isn't just storytelling; it's a masterclass in pattern recognition, strategic response, and hard-earned wisdom.
These are REAL experiences from two executives who've navigated decades in corporate America. We're not just sharing war stories - we're breaking down what was actually ha...
Mark as Played
Episode 29 | Jason Averbook on 4 Forces Reshaping Work: Why AI Transformation Isn't About Technology
December 19, 2025 • 55 mins
🚀 Jason Averbook reveals the 4 forces creating the biggest change HR has ever seen—and why 95% of AI projects are failing. This isn't about technology; it's about trust, engagement, and fundamentally rethinking how work gets done.
⚡ THE 4 FORCES RESHAPING WORK:
1. Engagement is slipping (trust in companies at all-time lows)
2. Jobs and skills are changing rapidly
3. Early career on-ramp is broken
4. AI is being pushed into unp...
Mark as Played
Episode 28 | HR Tech's Top Analyst John Sumser: AI Reality, Career Reinvention & What's Broken in HR
December 12, 2025 • 52 mins
🚀 FROM FOOD CRITIC TO KITCHEN: John Sumser, HR tech's leading independent analyst for over 20 years, reveals what happens when you step from the sidelines into operations—and why most of what we believe about AI, HR, and career success is wrong. Learn how to navigate uncertainty as opportunity, why "I don't know" is the most powerful thing a leader can say, and what the next 5 years hold for HR in this candid conversation about tr...
Mark as Played
December 5, 2025 • 69 mins
Finland – Universal Basic Income Pilot🚀 THE CASE FOR GIVING PEOPLE MONEY: UBI expert Scott Santens reveals why the most radical idea in economics might be the simplest - just give people cash. Discover how Alaska has proven this works for 40+ years, why his crowdfunded basic income changed everything he thought about work, and what happens when we shift from survival mode to abundance thinking.
⏰ TIMESTAMPS:
00:00 Introduction:...
Mark as Played
November 21, 2025 • 58 mins
🔄 What happens when two leaders with completely different upbringings join forces? In this deeply personal episode, Amy and Meg explore how their vastly different childhoods - one marked by stability and support, the other by constant change and scarcity - shaped their leadership styles, decision-making approaches, and the way they navigate challenges today.
⏰ TIMESTAMPS:
00:00 Introduction & Banter including Meg's Vietnam trav...
Mark as Played
November 20, 2025 • 60 mins
What would you build if you were creating a product organization from scratch in 2030? SugarCRM Chief Product Officer Maksim Ovsyannikov joins Amy and Meg to explore how AI is fundamentally reshaping product development, design thinking, and organizational structures.
From "very little user experience" as a value proposition to why QA is more critical than ever in probabilistic systems, this conversation challenges everything yo...
Mark as Played
November 7, 2025 • 57 mins
🚀 After 24 episodes and conversations with 20+ transformation leaders, Amy reveals the AI Transformation Maturity Model that synthesizes everything we've learned. Discover how to get ahead of AI transformation instead of being a victim of change, why this moment offers the biggest career opportunity in decades, and how to build the change agility that separates thriving organizations from struggling ones.
This episode weaves toge...
Mark as Played
October 31, 2025 • 71 mins
🚀 INVENTING THE AI-FIRST OPERATING MODEL: HubSpot CEO Yamini Rangan reveals how she completely scrapped her $40B company's roadmap and rebuilt it AI-first. Learn how to pivot from volume to conversion, navigate the decline of SEO, and lead transformation when no one has the answers.
⏰ TIMESTAMPS:
00:00 Introduction: From Reading Every Book in the Library to CEO
05:00 Moving to the US: The Airport Story and Finding Her Voice
15:...
Mark as Played
October 17, 2025 • 62 mins
🚀 Why "I Don't Know Yet" Is the Most Valuable Leadership Skill in the AI Age: Dr. Kirstin Ferguson reveals how expertise becomes your biggest enemy and why intellectual humility beats certainty every time.
⏰ TIMESTAMPS:
00:00 Introduction & Antarctica Adventures
02:06 Welcome to Dr. Kirstin Ferguson
04:38 Why Travel Reduces Blindspots
05:49 The UK Post Office Scandal: When "The Computer Is Always Right"
08:44 How Success Becomes ...
Mark as Played
October 10, 2025 • 55 mins
🚀 BREAKING OUT OF THE DEFAULT MALE WORLD: Meg and Amy reveal the hidden challenges of female leadership in a world designed by and for men. Learn how to navigate bias, own your power, and redefine what leadership looks like in the AI era in this raw and empowering conversation.
⏰ TIMESTAMPS:
00:00 Introduction to Female Leadership Challenges
05:55 WNBA Success and Equal Pay Movement
07:06 Fiji Simo's Historic OpenAI Appointment
0...
Mark as Played
October 3, 2025 • 60 mins
Angela Le Mathon reveals how HR leaders can move beyond the "skills data trap" to drive real business outcomes with AI. Learn how to speak the language of business, avoid the employee experience trap, and design AI-native organizations in this thought-provoking conversation on business transformation and leadership.
**🔑 KEY INSIGHTS:**
Skills data works for talent marketplaces but doesn't drive business outcomes
HR must ...
Mark as Played
September 26, 2025 • 55 mins
🌐 Most companies are approaching AI adoption backwards. While executives push top-down strategies, the real innovation is happening in the trenches.
Seth Wylie reveals why successful AI transformation starts with the people already experimenting - not training programs or executive mandates.
**🔑 KEY INSIGHTS:**
- Why mandatory AI training kills experimentation before it starts
- The one question that gets everyone talking: ...
Mark as Played
Episode 18 | Sangeet Paul Choudary: The Winning AI Strategy – Reshuffling Systems, Not Adding Smarts
September 19, 2025 • 65 mins
Meg and Amy welcome Sangeet Paul Choudary, author of Reshuffle. Their discussion explores how companies must evolve beyond traditional operating models to embrace structural change. Sangeet highlights the often-overlooked role of coordination costs in organizations, how AI can help manage these costs, and why rethinking business models is central to AI transformation. He also shares insights on creating structural optionality and r...
Mark as Played
September 12, 2025 • 62 mins
This week on The Meg & Amy Show, Meg and Amy welcome fitness expert and wellness coach Angie Mercado. Angie shares her decades of experience helping women find joy in movement, balance demanding lives, and stay consistent with their health goals even when work, travel, and family make it difficult.The conversation explores breaking free from the “one-hour workout” mindset, strategies for staying fit while traveling, the importance ...
Mark as Played
September 5, 2025 • 62 mins
In the business of software, how you charge is just as important as what you build. In this episode of The Meg & Amy Show, Meg and Amy sit down with Kyle Poyar, creator of Growth Unhinged and one of the leading voices in SaaS pricing and monetization. Kyle coined the term Product-Led Growth, and in this conversation he unpacks the seismic shifts happening in pricing – from the rise of hybrid and usage-based pricing to the new front...
Mark as Played
August 28, 2025 • 57 mins
This week, Meg and Amy sit down with John Wookey, a legend in the enterprise software world, to explore the power of mission and values in organizations, why transparency is essential for strong leadership, and how AI is reshaping the way we work. John also reflects on the importance of unlearning outdated structures to foster innovation, and shares advice for first-time people managers.
John's Strategy 101 Paper: https://www.link...
Mark as Played
August 22, 2025 • 63 mins
In this episode of The Meg and Amy Show, Meg and Amy get personal, opening up about their individual health journeys and what inspired them to make wellness a priority. They share the turning points that pushed them to take action, what they discovered through their initial health scans, and the lifestyle changes they’ve embraced — from fitness routines to nutrition to smart supplementation.
Submit questions for future Leadership ...
Mark as Played
August 21, 2025 • 62 mins
Join Meg, Amy, and Gustavo Alba as they dive into the new rules of executive search, the evolution of talent profiles in the AI economy, and the new characteristics required for transformational leadership. Listen in to learn more about the challenges of navigating AI transformations in legacy companies, the need for bravery and vision in leadership, and survival tips for CEOs in the AI era.
Heidrick and Struggles | https://www.h...
Mark as Played
August 8, 2025 • 60 mins
In this episode of The Meg and Amy Show, Meg and Amy are joined by Usman Sheikh for an insightful conversation on the transformation of business models — from legacy organizations to the rise of new players. They explore the critical role of leadership in guiding organizations through disruption, the human impact of large-scale change, and why building personal agency is essential for thriving in today’s rapidly evolving world of w...
Mark as Played
August 1, 2025 • 48 mins
In this episode, Meg and Amy discuss the evolving landscape of organizational design and business models. They explore the complexity of communication in growing organizations, the need for redesigning structures to adapt to new technologies, and so much more. The conversation emphasizes the importance of curiosity, flexibility, and understanding the core principles of business as organizations navigate these changes.
Submit quest...
Mark as Played
Popular Podcasts
Gregg Rosenthal and a rotating crew of elite NFL Media co-hosts, including Patrick Claybon, Colleen Wolfe, Steve Wyche, Nick Shook and Jourdan Rodrigue of The Athletic get you caught up daily on all the NFL news and analysis you need to be smarter and funnier than your friends.
A curated mix of conversations celebrating the voices, journeys, and truths defining Black history today. Presented by The Black Effect Podcast Network. Where Black Thoughts Live!
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.