The Meg and Amy Show

WRKdefined Podcast Network
  • 5.0 (4)
  • Technology

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.

  1. 6d ago

    The Future of People Analytics Isn't About (Just) People

    People analytics has spent years analyzing people. Now it needs to analyze the work.  Recorded live at People Analytics World, Meg Bear and Amy Wilson make the case that as AI changes how work gets done, the function has to move past studying humans and start studying the system of work itself: how humans and AI share it, where it gets stuck and how it should be designed. They also discuss why the bottleneck in software was never the code, and why AI should change how the whole engineering organization works, not just the engineers. They also cover why "learn it, train it, deploy it" breaks down when AI keeps improving this fast, and why leaders need to keep learning too. From there, they get into what it takes to lead right now. It takes a special person who's willing to unlearn and relearn, and a special organization around them. They talk about why the manager job just got a lot harder and is likely to be split into separate roles. And they make the case that you can't start a movement alone. If you work in people analytics, lead teams or design how work gets done, this conversation is about the questions you'll face next. Subscribe for more from The Meg and Amy Show. TIMESTAMPS: 00:00 Welcome: Live from People Analytics World 02:14 David Green Keynote: A Teams vs B, C, D Teams 04:17 AI Use Cases Still Stuck in HR Topics 05:09 Work Design Goes Mainstream: From Evangelism to Urgency 06:44 DRI vs Dynamic Team: Prasad Setty and Amy's Debate 09:20 Why Committees Fail and Movements Need Co-Creators 10:40 Intel's Kelsey Klein: Real Work Redesign Use Cases 12:04 Changing the Organisation vs Changing the Individual 13:26 Software Dev Bottlenecks Are Not the Code 17:49 Bundling and Unbundling: Roles, AI Tasks and the Manager 20:06 Jack Dorsey's Model as an Extreme Provocation 22:12 Human-AI Systems: Measuring What Makes Humans Better 25:35 The Special Person and the Special Organisation 28:36 The Future of the People Analytics Role 30:56 Context Engines, Strategy Alignment and Sense-Making 34:25 Storytelling as a Core Analytics Skill 35:33 Dashboards Are Dead, Long Live Interactive Data Spaces 📚 RESOURCES: People Analytics World: https://home.paworld365.com/ PAWorld26 New York: https://home.paworld365.com/events/26nyc/ Ikona Analytics, our podcast stage host: https://www.ikonaanalytics.com/ Richard Rosenow: https://www.linkedin.com/in/richardrosenow/ "The End of People Analytics As We Knew It" (Ikona): https://www.ikonaanalytics.com/insights/the-end-of-people-analytics "Context Is All You Need" (Ikona): https://www.ikonaanalytics.com/insights/context-is-all-you-need Insight222 People Analytics Trends 2025/26 (David Green): https://go.insight222.com/insight222-people-analytics-trends-report-2025/26 Prasad Setty: https://www.gsb.stanford.edu/faculty-research/faculty/prasad-setty Siobhan Savage, Reejig: https://www.reejig.com/company/siobhan-savage "You Can't Redesign Work With a Team You Haven't Designed" (Amy): https://www.themegandamyshow.com/p/you-can-t-redesign-work-with-a-team-you-haven-t-designed "From Hierarchy to Intelligence" (Jack Dorsey & Roelof Botha): https://sequoiacap.com/article/from-hierarchy-to-intelligence Jaya Gupta on unbundling intelligence: https://x.com/JayaGup10/status/2101799427145183571 Our episode with Jason Cohen: https://wrkdefined.com/podcast/the-meg-and-amy-show/episode/hidden-ways-to-grow-without-more-hires-or-funding-jason-cohen Kieran Snyder: https://www.linkedin.com/in/kieran-snyder-60572987/ Morgan Depenbusch: https://www.linkedin.com/in/morgandepenbusch/ Bill and Morgan's Dashboard Confessionals: https://creators.spotify.com/pod/profile/bill-yost/ 🔗 CONNECT: Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show https://www.linkedin.com/in/megbear/ https://www.linkedin.com/in/amy-wilson-insight/ #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #HRTech #AIStrategy

  2. Sep 30 ·  Bonus

    Why Conway's Law Matters More in the Age of AI

    Why do Sales, Customer Success, and Engineering keep hitting the same friction? In this hot take, Meg Bear and Amy Wilson break down Conway's Law — the idea that your org structure shows up in how work gets done. From DRIs as a band-aid to why aligned incentives and shared goals matter more than boxes and roles, plus the Oracle story and why AI makes this urgent now. Subscribe for bold, exec-level takes on AI, leadership, and the future of work with The Meg and Amy Show. #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #ChangeManagement #AIStrategy

  3. Sep 25

    Hidden Ways to Grow Without More Hires or Funding | Jason Cohen

    Serial founder Jason Cohen shares hidden ways to grow without more hires or funding from his book Hidden Multipliers. Meg Bear and Amy Wilson dig into why negative reviews boost sales, the math behind keeping customers, and how to make frameworks actually fit your team. In this episode, Jason breaks down practical ideas leaders can use right away: - Why showing negative reviews builds trust, increases sales, and lowers returns - The churn math most teams miss — why keeping customers beats chasing new ones - How to make faster decisions with Fermi estimation - Who your best customer really is, and why the bottom 10% can drain profit - How to keep customer love as you scale, from Southwest to Workday - Why frameworks should fit like clothes — start off-the-rack, then tailor Jason Cohen is a serial entrepreneur and author of Hidden Multipliers. Meg Bear and Amy Wilson are former tech executives hosting The Meg and Amy Show on AI, leadership, and the future of work. TIMESTAMPS 00:00 Cold Open: Logo Churn Is Death 00:28 Introducing Jason Cohen 01:40 Engineering Mindset vs Strategic Thinking 03:09 A Smart Bear: Fermi Estimation and the Power of Ten 06:53 How Fermi Estimation Beats Scoring Rubrics 11:38 Why Jason Wrote Hidden Multipliers 14:24 Carol: The Ideal Customer Profile 16:51 Bazaarvoice Data: Negative Reviews Increase Sales 19:52 Strengths Are Proclivities: Context Changes Everything 25:36 The Workday Case Study: Love, Drift, and Disruption 28:03 Can You Scale and Keep Customer Love? 30:13 Culture, Founders, and Succession 36:37 Why Culture Cannot Live in One Person 38:55 The Math of Retention vs Net New Acquisition 40:55 Why Cancellation Is the Most Important Number 44:23 Customer Discovery: Hypothesis Before Interviews 50:30 Frameworks Are Clothes: Try, Tailor, or Reject 56:53 Closing Reflections 👉 Subscribe for weekly sharp takes for busy execs 👉 Tell us in comments: which multiplier will you try first? Links: https://andertoons.com/ https://en.wikipedia.org/wiki/Philip_E._Tetlock https://en.wikipedia.org/wiki/Law_of_trivialityhttps://longform.asmartbear.com/roi-rubric/ https://longform.asmartbear.com/https://skills.asmartbear.com/skills/asb-willingness-to-pay/ https://en.wikipedia.org/wiki/Enrico_Fermi https://www.linkedin.com/in/chanofernandez/ https://www.linkedin.com/in/hbrunner/ https://www.linkedin.com/in/reidhoffman/ https://www.linkedin.com/in/aneelbhusri/ https://www.linkedin.com/in/pattyazzarello/ #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #EnterpriseAI #CareerAdvice

  4. Sep 18

    Why AI Fails Without a New Operating Model with Kelley Steven-Waiss

    Your AI tools aren't broken. Your operating model is. Meg Bear and Amy Wilson sit down with Kelley Steven-Waiss, Founder of Novaworks, former CHRO, founder of Hitch (acquired by ServiceNow), and author of Valley Girls, to explain why so many AI pilots stall — and what great leaders do differently. Kelley shares why adding new tech on top of old ways of working leads to poor results, how to design a system of work that includes people, agents, and robots, and why she believes the CHRO role should evolve into Chief Work Officer. In this episode, you’ll learn: * Why AI fails when the operating model stays the same * How to map strategy to work before you add new tools * What strong AI leadership looks like in practice * How founders build resilience and the muscle for rejection About Kelley: Kelley Steven-Waiss is Founder of Novaworks, an AI-native system for managing the total workforce. She served as CHRO for 13 years, founded Hitch, and writes on leadership and the future of work. About the show: The Meg and Amy Show with former tech executives Meg Bear and Amy Wilson — bold takes on AI, leadership, and the future of work. References: https://home.paworld365.com/events/26sfo https://www.ikonaanalytics.com/ https://www.themegandamyshow.com/ https://www.stratechi.com/six-sigma/ https://www.linkedin.com/in/davewright2?trk=public_post_feed-actor-name https://www.linkedin.com/in/briansolis https://www.linkedin.com/in/kelleystevenwaiss https://www.amazon.com/Infinite-Visionary-Transform-Businesses-AI-Forward-ebook/dp/B0GZLNRLMS #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #EnterpriseAI #WomenInLeadership

  5. Aug 28

    Why Enterprise AI Fails at Work Design, Not Agents | Siobhan Savage

    Enterprise AI isn't failing because agents aren't smart enough — it's failing at work design. Reejig CEO Siobhan Savage joins Meg Bear and Amy Wilson to reframe AI transformation for the enterprise. The constraint isn't agent capability — it's aligning AI with workflows, org structure, and business outcomes. Siobhan breaks down why the workflow is now the core unit of work, how to build internal AI Work Design capability instead of outsourcing to consultants, and why transparent, human-centric change management beats token-based theater. In this conversation: - Why "AI-first" measured by token spend makes employees hate AI - Where humans stay in the loop — nothing is running end-to-end yet - Upgrade vs. reimagine: why you don't "vibe code the bank" - How the best companies get surgical with use cases — and why the CIO + CHRO + CFO trifecta matters With hosts Meg Bear and Amy Wilson — former tech executives tackling AI transformation, leadership, and the future of work with bold takes and real expertise. Chapters: 00:00 The dumbest "AI-first" metric leaders celebrate 00:52 Meet Siobhan Savage, CEO of Rejig 03:34 Reejig's mission - building the way the world works 05:21 How Reejig built 25 models of real work 07:50 Where automation lands today - sub-tasks, not jobs 09:40 It's not an agent problem, it's a work design problem 11:07 From tasks to workflows & the ROI shift 13:23 Who's actually buying - CIO + CHRO + CFO trifecta 16:22 Inside the AI Work Design team 20:34 Work Architects vs AI Work Designers vs Agent Builders 27:05 Job Architecture vs Work Architecture 31:07 Why the workforce is dysregulated right now 34:26 Being bold & responsible with AI 37:53 Stealth change management explained 42:18 Leaders must set expectations, not theater 46:42 Energy, structure & what lights Siobhan up 49:08 Leadership Corner - Should you hire a Chief of Staff? 58:28 AI vs human Chief of Staff Watch the Shorts from this episode on the channel all week. #aileadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #EnterpriseAI #AIStrategy

  6. Aug 7

    The Future of Work Has AI Agents in It. Payroll Isn't Ready. | Eynat Guez, Papaya Global

    The future of work has AI agents in it — and payroll isn't ready. Eynat Guez, co-founder and CEO of Papaya Global, joins Meg and Amy to explain why the 2030 workforce is humans and agents side by side, and why your compliance infrastructure better be ready. Eynat bet the company on owning the payment rails instead of expanding into HCM — and she did it "regulated by choice," taking on seven financial regulators globally. She breaks down why payroll sits at the intersection of HR and finance, why "move fast and break things" actively destroys value in regulated categories, and how she rolled out AI inside her own company by limiting usage first to protect employees from costly mistakes. ⏱️ In this episode: 00:00 Introduction and Open Water Swimming 03:16 The Strategic Bet: Payments Over HCM 06:14 Why Payroll Companies Don't Actually Pay People 08:00 Global Payroll Complexity and the Compliance Gap 11:00 Agentic Compliance Knowledge Base and AI Tools 12:32 How Papaya Tackles Cross-Border Payment Transparency 15:00 Fintech Regulation, KYC, and Anti-Money Laundering 16:35 Building Direct Local Bank Networks Across 150 Countries 18:50 Compliance as a Competitive Differentiator with Fortune 500 20:23 The End Worker Experience and Pay Date Liability 23:06 CyberArk Case Study: Same-Day Expert Support 28:07 AI Transformation Inside Papaya 30:24 Building the AI Infrastructure and Measuring 3x Efficiency 33:18 Change Management: Change the People or Change the People 34:46 Managing AI Token Costs and Usage Limits 37:29 The AI Maturity Self-Assessment Tool 40:28 AI Agents as Workers: The 2030 Workforce Vision 43:49 Real-Time Pay, Fractional Work, and Individual HR Systems 49:23 Where the Name Papaya Came From 50:13 Leadership Corner: Getting Your Team to See What You See 59:46 When You Know Your Vision Has Landed 01:01:11 Takeaways: The Translator Role and Systems Thinking Key insights you'll walk away with: 🎯 Why payroll companies don't actually pay people — and where the real value lives 🏦 The "regulated by choice" strategy that turned compliance into a moat 🤖 How to roll out AI to your team without letting it fail them 📈 Why the 2030 workforce means ten employers per person 🔑 Leadership Corner: How to know when a new idea has actually landed inside your organization Meg is a board member of Papaya Global. 📚 RESOURCES: Papaya Global: https://www.papayaglobal.com/ 🔗 CONNECT: Eynat Guez: https://www.linkedin.com/in/eynatguez/ Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show https://www.linkedin.com/in/megbear/ https://www.linkedin.com/in/amy-wilson-insight/ #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #AIStrategy #HRTech #globalpayroll

  7. Jul 31

    ⭐ We Tried GLP-1. Here's What Actually Happened. | Meg & Amy

    🚀 Two years in, and Amy and Meg bring the data. GLP-1 results, body composition breakthroughs, the metabolic reframe no one told them about — and the leadership question hiding inside every health conversation: are you building a life you don’t need to take breaks from, or just managing to survive the one you’re in? ⏰ TIMESTAMPS: 00:00 Introduction 01:59 Announcements: Textio Board & HR Tech 1000 8:42 Health Journey: Year-Two Check-In 11:32 GLP-1 — What Actually Changed 22:32 Body Composition Results & The Cost Question 28:18 Community, Trust & Staying the Course 31:20 Leadership Corner: How Much Should I Care? 39:27 Energy Systems & Sleep as a Leadership Metric 45:32 Closing Thoughts & Patty Azzarello’s Question 🔑 KEY INSIGHTS: - GLP-1 didn’t just drive weight loss — it unlocked the performance Amy had been building toward for two years. The drug and the habits compound; neither works as well alone. - For women, hormonal reality means “cut calories and work out” often doesn’t produce the results it promises men. GLP-1 can level the metabolic playing field. - Sleep is Meg’s #1 performance input — above exercise, body fat, or any other metric. When cognitive fitness goes, everything else follows. - The people who celebrate you when things are good (not just support you when things are hard) are the ones worth keeping close. Community isn’t optional on a health journey — it’s infrastructure. - Self-care isn’t what you do on vacation. It’s building a life you don’t need to take breaks from — one decision, one habit, one honest conversation at a time. 📚 RESOURCES: Weightless by Dr. Rocio Salas-Whalen (the GLP-1 protocol book Meg references): https://weightlessthebook.com/ Why Is SHE Still Here? by Patty Azzarello (the memoir with the question Meg had to write down): https://pattyazzarello.com/books/ Remedy Meds (Amy’s GLP-1 source — online, out-of-pocket, $299/month): https://remedymeds.com/ 🔗 CONNECT: Meg Bear: https://www.linkedin.com/in/megbear/ | https://megbear.com Amy Wilson: https://www.linkedin.com/in/amy-wilson-insight/ Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show YouTube: https://www.youtube.com/@TheMegandAmyShow #GLP1 #WomensHealth #HealthJourney #WeightLossJourney #Biohacking #HealthyLiving #Leadership #Burnout #MegAndAmyShow

  8. Jul 24

    You’re not broken. The system is. | Laurie Ruettimann

    🚀 Laurie Ruettimann has been saying the things HR won't say for twenty years — and she's starting to wonder if any of it worked. In this conversation, she argues that most advice is projection, financial freedom is the foundation of authenticity rather than a brand strategy, and AI isn't what's making work unbearable. She also gets emotional on mic. And tells us about the thank-you notes she wrote after putting her cat down. ⏰ TIMESTAMPS: 00:00 Introduction — Laurie Ruettimann 04:33 Inventing a life you can actually control 11:19 Financial freedom, overwork, and detachment at work 16:54 Reading outside your industry and the empathy gap 25:41 Personal brand, haters, and authenticity as a class issue 36:57 The honest question: has this work been worth it? 44:28 AI anxiety vs. what's really making work hard 49:59 The Roxy letters — why people keep showing up 52:01 Leadership Corner: restructuring, lesser roles, and severance 🔑 KEY INSIGHTS: - Most advice is projection. When Laurie sits with clients now, she rarely gives advice — she witnesses. And she tells them what they actually need to hear: "It's not you. You're not broken. The system is broken." - Financial freedom isn't a brand strategy — it's a precondition. You can't be authentic when you're still paying student loans. "Be yourself" only lands once you can afford to leave. - Career advice was built for whoever got into power first. Most of it doesn't work the same for women or people of color — because it reflects the tactics of a cohort that was mostly male. - The number one thing working parents worry about isn't AI. It's the cost of childcare. Blaming AI for workplace anxiety misses the structural problems that were already there. - The secret to being a more empathetic leader isn't a leadership course. It's reading outside your industry — geopolitics, historical fiction, stories from contexts nothing like your own. 📚 RESOURCES: Betting on You by Laurie Ruettimann: https://laurieruettimann.com/books/betting-on-you/ Incorruptible by Eric Ries: https://www.incorruptible.co/ 🔗 CONNECT: Laurie Ruettimann: https://www.linkedin.com/in/laurieruettimann/ Meg Bear: https://www.linkedin.com/in/megbear/ | https://megbear.com Amy Wilson: https://www.linkedin.com/in/amy-wilson-insight/ Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show YouTube: https://www.youtube.com/@TheMegandAmyShow #CareerAdvice #FinancialFreedom #WorkplaceTruths #Leadership #HRLeadership #CareerDevelopment #WomenInWork #AuthenticLeadership #MegAndAmyShow

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5
out of 5
4 Ratings

About

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.

Information

  • Creator
    WRKdefined Podcast Network
  • Years Active
    2025 - 2026
  • Episodes
    59
  • Rating
    Explicit
  • Copyright
    © All rights reserved by WRKdefined
  • Show Website
    The Meg and Amy Show

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