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
October 23, 2026 • 51 mins
Why hasn't AI showed up in the P&L yet?
Heidrick & Struggles CEO Tom Monahan joins Meg and Amy. His one question that reveals your real capability gap: If you just told your team to go do that, what wouldn't happen? Tom unpacks why the CEO job is now a two-way ambassador role, and why moving AI from the CEO story to the CFO numbers is the real test.
He also makes the case for managers in an age of flat org charts, and why...
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October 16, 2026 • 62 mins
What Every Executive Woman Should Know About Perimenopause with Dr. Jessica Kassis
OB-GYN Dr. Jessica Kassis missed her own perimenopause for a year - until her primary care doctor caught it. She joins Meg and Amy to explain why high-performing women miss the signs at work, how to talk to your doctor, and what actually helps with brain fog, rage, sleep, and burnout.
We cover #perimenopauseatwork , #brainfogperimenopause , h...
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October 13, 2026 • 12 mins
HubSpot CEO Yamini Rangan shared a layoff memo for 660 employees.
As longtime operators, Meg and Amy break down what she got right (and wrong) about leading with clarity, humanity, and accountability in a hard moment, and what other leaders can learn from it.
What we cover:
- Why this memo stood out from most layoff announcements
- What Yamini got right on principles, focus, and severance
- What was missed on market pressure, ...
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October 9, 2026 • 64 mins
AI won't fix a broken process — it makes outcomes worse. Stacey Harris shares new results from the 29th Annual HR Systems Survey on what actually drives better outcomes.
Former tech executives Meg Bear and Amy Wilson sit down with Stacey Harris, Chief Research Officer at Sapien Insights Group, to break down 29 years of HR tech data and what it means for leaders working on AI, HR tech, and the future of work.
Stacey explains...
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October 2, 2026 • 37 mins
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 ...
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September 30, 2026 • 8 mins
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,...
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September 25, 2026 • 59 mins
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
...
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September 18, 2026 • 63 mins
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 i...
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August 28, 2026 • 63 mins
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 capabili...
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August 7, 2026 • 64 mins
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...
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July 31, 2026 • 49 mins
🚀 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 H...
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July 24, 2026 • 64 mins
🚀 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....
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🚀 Jess Von Bank has spent 20+ years on every side of the HR tech problem — vendor, buyer, analyst, practitioner. She co-founded Now to Next to close the distance between an AI strategy and human outcomes, and she's writing her way through it publicly with the Human Thesis, a seven-part Substack series, and her forthcoming book Work Like a Mother. In this conversation, Jess makes the case that most organizations are running A...
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July 10, 2026 • 60 mins
🚀 AI didn't add a new chapter to the software story — it restarted the book at page one. In this solo episode, Meg and Amy explain why that makes sensemaking the scarce skill right now, who earns the role that survives every era of disruption, and what it actually looks like to stop waiting and build.
🔑 IN THIS EPISODE:
- The agentic HR moment: NovaWorks and SOL just came out of stealth — two agentic HCM platforms,&...
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June 27, 2026 • 54 mins
🚀 You're Not Unmoored. You're Unchained. | Nick Mehta on identity, reinvention, and the AI reckoning hitting every SaaS company. After stepping down as Gainsight CEO, Nick joins Meg & Amy to reframe what comes after the title ends — and breaks down forward deployed engineers, "token maxing," and why AI-native startups generate 10x the revenue per employee.
⏰ TIMESTAMPS:
00:00 Cold open: unmoored vs. unchained
01:25 ...
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🚀 The AI rush of 2025 didn't move the skills agenda forward — it stalled it. That's the contrarian read from the founder of Degreed, the company built to make skills the currency of the workforce.
David Blake walks us through why he thinks 2026 is the most important year of your career, what leader-led learning looks like when agents can actually run it for managers who were never trained to teach, and why he survives the S...
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June 12, 2026 • 60 mins
🚀 Maria Colacurcio asked her own AI agent to pull a code repository. Three times. It refused — and directed her to men on her team. That moment is the throughline of an episode about what's actually breaking in compensation, what AI buyers will spend on now, and the org-design conversation every founder is dodging.
Maria is the CEO of Syndio — the company that defined the market for pay-equity software and is now pio...
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June 5, 2026 • 60 mins
🚀 Amy and Meg dig into Jaya Gupta's "experience is now a tax" frame — and what actually survives when AI makes credentials look like overhead. Learn why the most golden job for the next decade is the translator role, how to stop optimizing AI for speed and start using it as an anxiety reducer, and why "manager wars" is the wrong fight to be picking right now, in this conversation on business transformation and leadership in ...
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May 29, 2026 • 59 mins
🚀 Running Pilots Is Not a Strategy: Charlene Li — three-decade authority on disruptive leadership and co-author of Winning with AI: The 90-Day Blueprint for Success — breaks down the consistent failure mode she's watched leaders repeat across the internet, social media, and now AI. Learn why "adapting" beats "adopting," why reinvention is the real AI opportunity (not efficiency), and the structural risk no one is namin...
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May 22, 2026 • 60 mins
Han-Shen Yuan — who led mobile engineering at eBay and Netflix and took Upwork to IPO as SVP of Engineering — explains why AI transformation is a constraint problem before it's a software problem. Learn why the real bottleneck is rarely the technology, what a "loose grip on your identity" means for senior leaders right now, and why cutting headcount on the back of AI productivity gains is eating your own future, in this...
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