Amy Wilson

Spent 20 years building Workday & SAP products used by millions. Operator view on leading teams — practical, people-first, no hype.

PODCAST

AI Won't Fix a Broken Process: Stacey Harris Shares Survey Data

Oct 9, 2026

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1 min read

AI Won't Fix a Broken Process: Stacey Harris Shares Survey Data

Stacey Harris | Episode #58

Meg Bear, +1

HOT TAKE

HubSpot Layoff Memo: What She Got Right (and Wrong)

Oct 8, 2026

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2 min read

HubSpot Layoff Memo: What She Got Right (and Wrong)

660 roles cut. One memo that was clearer and more human than most. Here's our breakdown.

Amy Wilson, +1

PODCAST

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

Oct 2, 2026

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2 min read

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

Live from PA World | Episode #57

Meg Bear, +1

PODCAST

Hidden Ways to Grow Without More Hires or Funding

Sep 25, 2026

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2 min read

Hidden Ways to Grow Without More Hires or Funding

Jason Cohen | Episode #56

Meg Bear, +1

HOT TAKE

Stop Clarifying Roles. Start Aligning Incentives.

Sep 22, 2026

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3 min read

Stop Clarifying Roles. Start Aligning Incentives.

How you organize your teams is how your business actually runs — and what Conway’s Law teaches us about fixing friction right now.

Amy Wilson, +1

ARTICLE

Sep 20, 2026

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6 min read

Alignment on Alignment

The market rewards reliability. Real alignment needs a global floor.

Amy Wilson

PODCAST

Why AI Fails Without a New Operating Model

Sep 18, 2026

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1 min read

Why AI Fails Without a New Operating Model

Kelley Steven-Waiss | Episode 55

Meg Bear, +1

HOT TAKE

The Boulder Is Moving: Why AI Safety Can't Wait

Sep 14, 2026

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3 min read

The Boulder Is Moving: Why AI Safety Can't Wait

A researcher exit, rare agreement among AI leaders, and the 3 risks every executive should understand right now

Amy Wilson, +1

LEADERSHIP CORNER

Sep 11, 2026

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1 min read

Role Eliminated in a Restructuring?

Don't Pick a Side

Meg Bear, +1

LEADERSHIP CORNER

AI Can't Do This: The Real Value of a Chief of Staff

Sep 4, 2026

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1 min read

AI Can't Do This: The Real Value of a Chief of Staff

Leadership Corner

Meg Bear, +1

ARTICLE

You Can't Redesign Work With a Team You Haven't Designed

Sep 1, 2026

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8 min read

You Can't Redesign Work With a Team You Haven't Designed

The AI work designer isn't one job. It's six — and you probably already employ most of them.

Amy Wilson

PODCAST

Aug 28, 2026

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2 min read

Why Enterprise AI Fails at Work Design

Siobhan Savage | Episode 54

Meg Bear, +1

LEADERSHIP CORNER

The 7-Step Method for Selling Heretical Ideas at Work

Aug 21, 2026

•

1 min read

The 7-Step Method for Selling Heretical Ideas at Work

"How Do I Get Them To See What I See?"

Meg Bear, +1

HOT TAKE

Why "Human in the Loop" AI Governance Is Failing

Aug 14, 2026

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1 min read

Why "Human in the Loop" AI Governance Is Failing

(in Both Directions)

Meg Bear, +1

ARTICLE

A Love Letter to Product Managers - This is Your Moment (Don't Blow It)

Jun 11, 2026

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4 min read

A Love Letter to Product Managers - This is Your Moment (Don't Blow It)

This one's for the many hundreds of you who've worked for me over the years, and for every product person feeling the ground shift under them right now. I need you to hear this, because I'm watching too many of you miss this moment.

Amy Wilson

ARTICLE

Jan 16, 2026

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3 min read

20 Must-Watch Leadership Moments

The Meg & Amy Show Season 1

Amy Wilson

ARTICLE

Oct 21, 2025

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5 min read

From Theory to Practice

How Sangeet Choudary's Systems Thinking Unlocks Real AI Transformation

Amy Wilson

ARTICLE

Oct 7, 2025

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4 min read

Why Retention is a Terrible Metric

(And What Leaders Should Focus on Instead)

Amy Wilson

ARTICLE

Sep 30, 2025

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5 min read

Building Board-Ready Business Cases

Jen Morrow's Proven Framework

Amy Wilson

ARTICLE

Sep 20, 2025

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5 min read

Why AI Is Breaking Every Pricing Model

(And What Comes Next)

Amy Wilson

ARTICLE

Aug 20, 2025

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7 min read

Stop Training People on AI.

Fix Your Business Model Instead.

Amy Wilson

ARTICLE

Aug 14, 2025

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4 min read

The Death of SaaS As We Know It

(And Why That's Actually Good News)

Amy Wilson

ARTICLE

The AI Transformation Paradox: Why Today's Innovation is Tomorrow's Table Stakes

Aug 13, 2025

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2 min read

The AI Transformation Paradox: Why Today's Innovation is Tomorrow's Table Stakes

A new framework for understanding the accelerating pace of AI transformation

Amy Wilson

ARTICLE

Aug 5, 2025

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4 min read

Building AI-Ready Companies:

The New Rules of Organizational Design

Amy Wilson

Amy Wilson

AI Won't Fix a Broken Process: Stacey Harris Shares Survey Data

HubSpot Layoff Memo: What She Got Right (and Wrong)

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

Hidden Ways to Grow Without More Hires or Funding

Stop Clarifying Roles. Start Aligning Incentives.

Alignment on Alignment

Why AI Fails Without a New Operating Model

The Boulder Is Moving: Why AI Safety Can't Wait

Role Eliminated in a Restructuring?

AI Can't Do This: The Real Value of a Chief of Staff

You Can't Redesign Work With a Team You Haven't Designed

Why Enterprise AI Fails at Work Design

The 7-Step Method for Selling Heretical Ideas at Work

Why "Human in the Loop" AI Governance Is Failing

A Love Letter to Product Managers - This is Your Moment (Don't Blow It)

20 Must-Watch Leadership Moments

From Theory to Practice

Why Retention is a Terrible Metric

Building Board-Ready Business Cases

Why AI Is Breaking Every Pricing Model

Stop Training People on AI.

The Death of SaaS As We Know It

The AI Transformation Paradox: Why Today's Innovation is Tomorrow's Table Stakes

Building AI-Ready Companies:

Get in the Loop