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PODCAST

The Meg and Amy Show

WRKdefined Podcast Network

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.

technology careers

All Episodes

70:34

Episode 23 | The Explorer CEO: Yamini Rangan on...

The Meg and Amy Show ·

2025/10/31

🚀 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 15:50 Immigration, Grit, and Tools for Navigating the Unknown 25:30

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62:26

Episode 22 | Dr. Kirstin Ferguson on The Curse of...

The Meg and Amy Show ·

2025/10/17

🚀 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 the Enemy of Adaptation 10:50 The Power & Authority Problem: Why

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55:41

Episode 21 | Female Leadership in a World Built for Men

The Meg and Amy Show ·

2025/10/10

🚀 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 08:09 AI Bias: ChatGPT Recommends Lower Salaries for Women 14:17

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60:22

Episode 20 | Angela Le Mathon: Speaking the Language...

The Meg and Amy Show ·

2025/10/03

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 shift from talking about programs and platforms to speaking outcomes

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54:19

Episode 19 | Seth Wylie: Stop Training, Start...

The Meg and Amy Show ·

2025/09/26

🌐 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: "What have you been experimenting with this week?" - How to connect

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65:05

Episode 18 | Sangeet Paul Choudary: The Winning AI...

The Meg and Amy Show ·

2025/09/19

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 reimagining software development for a rapidly changing

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62:52

Episode 17 | Angie Mercado: Finding the Joy in Fitness

The Meg and Amy Show ·

2025/09/12

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 of jumping for bone health and longevity, and how community and

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62:27

Episode 16 | Kyle Poyar: Software Pricing in the AI Era

The Meg and Amy Show ·

2025/09/05

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 frontier of AI ARR.Save your spot for Kyle's upcoming keynote: How to

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57:04

Episode 15 | John Wookey: Strategy, AI, and the Art...

The Meg and Amy Show ·

2025/08/29

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.linkedin.com/in/john-wookey/recent-activity/documents/ Books: The Silk

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62:42

Episode 14 | Our Health Journeys

The Meg and Amy Show ·

2025/08/22

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 Corner segments to: amywilsonadvisor@gmail.com Resources &

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62:49

Episode 14 | Gustavo Alba: Why Yesterday's Star CEOs...

The Meg and Amy Show ·

2025/08/15

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.heidrick.com/en Articles: Thrive-backed accounting firm Crete to

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60:03

Episode 12 | Usman Sheikh: Transformation from...

The Meg and Amy Show ·

2025/08/08

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 work. High Output Ventures | https://www.hov.co/ Usman's Blogs:

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48:43

Episode 11 | Building AI-Ready Companies: The New...

The Meg and Amy Show ·

2025/08/01

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 questions for future Leadership Corner segments to:

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55:18

Episode 10 | Kieran Snyder: Why Your AI Strategy is...

The Meg and Amy Show ·

2025/07/25

In this episode, Meg and Amy sit down with Kieran Snyder for a candid, high-impact conversation about leadership, life, and what it really means to be an AI-first company. They discuss why data storytelling matters more than ever, what authentic allyship looks like beyond performative gestures, and how to lead in the age of AI. Submit questions for future Leadership Corner segments to: amywilsonadvisor@gmail.com Resources & Mentions Kieran's Blog: You've Heard of AI-native Products. What About

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60:42

Episode 9 | From Surviving to Thriving: Our Take on...

The Meg and Amy Show ·

2025/07/18

In this episode, Amy takes center stage to dive into a topic we all need to talk more about – financial independence. Meg and Amy unpack how your upbringing and early money messages shape your relationship with finances, why your financial state is deeply tied to your mental well-being, and how to shift your mindset from survival to intention.Submit questions for future Leadership Corner segments to: amywilsonadvisor@gmail.com Resources & Mentions Books: Nickel and Dimed: On (Not) Getting By in

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57:32

Episode 8 | Jen Morrow: Building a Board Ready...

The Meg and Amy Show ·

2025/07/11

In today’s episode, Meg and Amy welcome Jen Morrow to the show! Jen shares practical tips for building a board ready business case with a powerful story, aligning stakeholders around a shared vision, and how to move forward when the answer is "no". Submit questions for future Leadership Corner segments to: amywilsonadvisor@gmail.com Connect with Meg, Amy, and Jen Jen's LinkedIn: https://www.linkedin.com/in/jenmorr/ Instagram: https://www.instagram.com/megandamyshow/ LinkedIn:

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39:24

Episode 7 | Leadership Corner Recap Show

The Meg and Amy Show ·

2025/06/20

While Meg & Amy are on vacation, we’re bringing you a Leadership Corner supercut! In these candid segments, Meg, Amy, and their guests tackle audience questions and share bold, practical advice on the hottest leadership topics of today. Submit questions for future Leadership Corner segments to: amywilsonadvisor@gmail.com Connect with Meg and Amy Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show Meg’s Website:

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62:04

Episode 6 | Dave Lu: Abundance Mindset Building ROI...

The Meg and Amy Show ·

2025/06/13

In this episode, Meg and Amy welcome Dave Lu, Silicon Valley tech veteran, startup founder, investor, activist, Emmy Award-winning producer, and host of the brand new podcast, Hyphen Nation with Dave Lu. The three discuss his experiences as a tech veteran and advocate for the Asian American community. He shares insights on the importance of self-advocacy, the impact of cultural expectations, the differences between a scarcity mindset and an abundance mindset, and so much more.Submit questions for

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47:22

Episode 5 | Retention Is a Terrible Metric: From...

The Meg and Amy Show ·

2025/06/06

The engagement numbers are in, and they're not great – but Amy and Meg argue we're measuring the wrong things entirely. In this episode, they challenge the obsession with retention, introduce the concept of "negative work," and make the case for why great managers are more crucial than ever in an AI-driven world. From bike shedding to leadership in crisis, this conversation will change how you think about what actually drives workplace success.Submit questions for future Leadership Corner segments

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44:58

Episode 4 | Inventing the Future of Software Business...

The Meg and Amy Show ·

2025/05/30

In this episode, Amy and Meg tackle the complexities of business model shifts in the software industry. The conversation delves into the transition from traditional SaaS models to agentic solutions, exploring new market opportunities and the impact of AI on your role.Submit questions for future Leadership Corner segments to: amywilsonadvisor@gmail.com In this episode, Meg and Amy unpack: – Pricing model shifts – The transition from on-prem to SaaS to agentic systems – How AI is impacting

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