330 - A career in pivots: Dean Carter on purpose, play, and taking big swings

Conor Sweeney joined us on The Modern People Leader. We talked about what it's looked like to scale culture while doubling in size every year for three years straight.----  Sponsor Links:🔗 Schedule a consultation with Manifest🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Explore the 2026 ​Deloitte Human Capital Trends ReportMPL Links:🔗Go sign up for MPL Build.----  (12:05) Lessons From Jessica Swank and Tiffany Stevenson(12:40) Learning Patience, Empathy and Flexibility as a Leader(18:25) What Form Health Does in Plain English(21:30) Scaling Culture While Form Health Doubles in Size(23:25) The Fork in the Road: What to Keep and What to Let Go(25:05) Why Consensus-Driven Decision-Making Stops Scaling(28:00) Trust as the Foundation for Faster Decision-Making(31:15) How to Scale Trust Day to Day(32:35) Why Nailing the Fundamentals Still Matters(33:25) Hiring for Both the What and the How(35:40) “Don’t Crush the Butterfly” and What Form Health Must Protect(36:30) Form Health’s First Butterfly: Clinical Care Quality(38:45) Form Health’s Second Butterfly: Partnership(43:20) Build With, Not Build For, as a People Leader(45:30) Project Compass and Form Health’s Job Architecture Upgrade(48:00) Building Consistency Around Levels, Competencies and Compensation(49:15) Building Job Architecture for the Next Phase of Growth(51:10) Why People Leaders Can’t Only Rely on Old Benchmarking Tools(53:00) The Rise of the High-Impact Individual Contributor(56:00) The Player-Coach Model of Modern Management---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Alexis Fink joined us on The Modern People Leader. We talked about how AI is changing work, why org design needs to move beyond boxes and lines, and how curiosity, influence, courage, and better systems thinking can help people leaders design for the future.----  Sponsor Links:🔗 Schedule a consultation with Manifest🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Learn more about SixFiftyMPL Links:🔗Go sign up for MPL Build.----  (14:10) The One-Way Door of AI and Work(17:15) Why AI Transformation Will Take Longer Than 18 Months(19:05) What Org Design Means in the AI Era(20:30) Work Organization, Decision Rights and the Role of Machines(22:15) Why the Org Chart Is the Wrong Question(23:05) Inverted Pyramids, Hourglass Models and Different Assumptions About Talent(25:00) The IKEA Example: Turning Automation Into New Human Work(28:05) Why AI Should Free Capacity, Not Just Eliminate Jobs(31:40) How to Reframe the Headcount Reduction Conversation(33:25) Breaking Through Constraints, Vendor Issues and Learned Helplessness(36:45) Budget Constraints and the Problem With Legacy Decision Rights(40:20) Lessons From Past Transformations at Microsoft(43:00) Creating a Hard Gate for Vice President Promotions(44:10) Creating a Real Individual Contributor Career Path(47:30) What Has Changed About Change Management(49:05) Multiple Layers of Change and the Need for a Clear North Star(50:25) Avoiding Shiny Object Syndrome and Finishing the Last Mile(53:10) The Difference Between Influence and Convincing(55:45) Creating Gravitational Pull Instead of Pushing---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Dean Carter (Best-Selling Author, 4x CHRO, & CEO of Instill)  joined us on The Modern People Leader. We talked about the career pivots that shaped his life, what Patagonia taught him about purpose and play, and why trusting your gut, taking big swings, and doing the right thing can lead you somewhere better than the plan you originally had.----  Sponsor Links:🔗 Explore the 2026 ​Deloitte Human Capital Trends Report🔗 Learn more about SixFiftyMPL Links:🔗 Go sign up for MPL Build.----  (12:30) Dean’s Career Story Through Life Pivots(23:20) The Moment Dean Decided to Work in HR(28:45) Choosing His Daughter Over Career and Leaving Fossil(33:40) Choosing Patagonia Over Bigger Career Moves(37:50) Work as Play(39:00) Humility, Simplicity and Living the Patagonia Way(41:40) Dean’s Advice for People Considering a Major Career Pivot(43:20) Showing Up Fully After You Make the Choice(46:30) Making the Best of Any Choice You Make(48:40) Why Big Misses Mean You Are Swinging Hard Enough(50:00) Career Emergence and How the Path Reveals Itself(56:10) Building AI That Saves Jobs Instead of Taking Them(58:25) Career Advice: Think Two Jobs Up, Not One Job Up---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

D.V. Williams, Chief People Officer from Match Group joined us on The Modern People Leader. We talked about why Match is betting on Gen Z talent, how skills are replacing titles as the new currency of work, and how Match is thinking about flexible mentorship and early-career programs.----  Sponsor Links:🔗 Learn more about Beqom at beqom.com/mpl🔗 Learn more about Tilt at hellotilt.com/mplMPL Links:🔗 Go sign up for MPL Build.----  (10:45) Why Match Is Betting on Gen Z Talent(12:00) Why Product and People Strategy Need to Align(15:20) How Gen Z Thinks About Work Differently(17:00) How Tinder Improved Engagement and Shifted the Internal Culture(18:20) Becoming Product-Led and Consumer-Focused(19:00) Flattening the Org and Getting Doers Closer to Decisions(23:45) Why Tenure and Title Are Outdated Proxies for Value(24:20) Skills as the New Currency of Work(24:45) Rebuilding Mentorship Around Skill Acquisition(25:20) Flexible Mentorship and the “Tinder for Skill Acquisition” Idea(30:15) How Match Is Approaching AI Internally(31:00) Equipping Employees With AI Without Framing It as Headcount Reduction(31:20) Match’s AI Day and Employee-Led Experimentation(34:00) How Dating Apps Are Evolving With AI and IRL Experiences(35:00) Using AI to Help People Show Up More Authentically on Dating Apps(40:15) Match’s Cross-Functional Rotational Program(41:30) Match’s Internship Program: 20,000 Applicants for 26 Roles(43:35) How the 2026 Rotational Program Is Different From Traditional Programs(45:35) Why Curiosity Beyond the Job Description Matters(48:05) Focusing Development on Skill Acquisition, Not the Next Title---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Christy Lake, Chief Administrative Officer at Twilio, joined us on The Modern People Leader. We talked about how AI is changing work, why skills, governance, and human judgment matter more than ever, and how Twilio is thinking about remote-first work, employee experience, and curiosity in the AI era.----  Sponsor Links:🔗 Learn more about SixFifty🔗 Explore the 2026 ​Deloitte Human Capital Trends ReportMPL Links:🔗 Go sign up for MPL Build.----  (11:20) The Hardest Thing on Christy’s Plate as CAO(12:00) Why AI Is the Biggest Transformation Christy Has Seen(13:00) Upskilling, Security, Data and Governance in the AI Era(14:30) Why AI Does Not Have a Clear Playbook Yet(15:25) Why This AI Cycle Comes With So Much Fear(17:30) Building a Skills Infrastructure for the Future of Work(18:15) Tasks, Roles and Where Human Judgment Still Matters(19:15) Twilio’s Three-Horizon View of AI Change(25:00) The Task Construct of Work and AI-Able Work(26:00) Why Existing Companies Still Need Org Design and Change Management(29:00) The Future of Employee Experience and the One Prompt Box(31:15) Why UX Will Matter More in the Future of Work(32:00) Why Companies Should Not Move Too Fast Without Human-in-the-Loop Design(33:40) Why People Still Need to Be Seen, Recognized and Thanked(36:00) Why Twilio Stayed Remote First(38:10) Hiring From Anywhere and Becoming a Net Talent Winner(40:45) Remote-First Companies and AI-First Readiness(42:00) AI Burnout, Remote Work and the Pressure to Do More(44:10) Why AI Upskilling Is Becoming Nights-and-Weekends Work(48:05) Why Constant Change Leaves People Without a Sense of Mastery---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Becks Port, Chief People Officer at Okta, joined us on The Modern People Leader. We talked about why AI agents should be treated like digital coworkers, how Okta is thinking about agents on the org chart, and what the future of HR, career development, security, and team design could look like as humans work alongside machines.----  Sponsor Links:🔗 Learn more about Beqom at beqom.com/mpl🔗 Learn more about SixFiftyMPL Links:🔗 Go sign up for MPL Build.----  (07:45) AI Agents as Coworkers and Digital Workers(08:20) Why Agents Need Managers, Accountability and Clear Handoffs(09:00) Which AI Agents Belong on the Org Chart(11:10) Deconstructing and Reconstructing Roles Around AI(13:15) How AI Is Creating New Roles at Okta(15:45) Why Okta Is Adding an Agentic Coach to the Org Chart(18:20) Decision-Making With Human and Agentic Coworkers(19:10) Why Task-Level Granularity Matters for AI Delegation(20:45) Okta’s Head of AI Transformation Role(21:15) Building Agentic Coaches and Onboarding Agents(22:00) Upskilling Employees to Become AI Proficient(23:15) The Future Structure of the People Team(25:00) Coaches, Advisors, Workforce Architects and Embedded Tech Talent(27:10) Why AI Proficiency Is the Safest Career Bet(29:10) Why Graduate Programs and Rotational Programs May Make a Comeback(32:35) Why Getting an Agent on the Org Chart Is a 12-Month Process(34:35) Securing AI Agents, Access and Kill Switches(37:30) Digital Colleagues That Never Sleep(40:05) Why Future Teams May Be Organized Around Processes Instead of Functions---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Clare Bonham (Chief Product Officer) and Sébastien Baehni (CTO) from beqom joined us on The Modern People Leader. We talked about how managers can make better pay and performance decisions, why AI should support but not replace human judgment, and what intentional AI looks like in compensation.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode326 Sponsor Links:🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Learn more about Beqom at beqom.com/mpl🔗 Explore the 2026 ​Deloitte Human Capital Trends Report MPL Links:🔗Go sign up for MPL Build.----  (10:45) Why Managers Need Context for Pay and Performance Decisions(11:35) Pay History, Pay Range, Budget and Talent Data(14:40) The Evolving Role of Managers in Compensation Decisions(16:05) The Difference Between Owning the Decision and Just Delivering the Message(17:45) How Managers Should Talk About Pay Constraints With Employees(23:05) Hiding Complexity While Letting Managers Drill Down(25:05) Why People Do Not Want AI Fully Deciding Their Compensation(26:15) Why AI Should Help but Humans Should Stay in Control(29:25) The Three Principles of Intentional AI: Explainable, Collaborative and Controllable(31:45) Why Compensation and Performance Decisions Must Stay Human-Centered(34:10) Auditing the Data, Rules and Models Behind a Pay Decision(36:10) The Three Types of AI in Compensation and Performance(38:45) Why LLMs Should Not Make Compensation Calculations(39:30) Why Compensation Needs Correctness, Not Plausibility(40:35) Moving Comp Teams Away From Spreadsheet-Heavy Work(41:20) Refocusing Comp Professionals on Strategy, Fairness and Incentives(48:05) The Rise of the High-Impact Individual Contributor(50:05) Why Automating Easy Tasks Could Increase Burnout---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Heather Dunn, Chief People Officer at Brex, joined us on The Modern People Leader. We talked about Brex’s rapid acquisition by Capital One and how Heather led through diligence, communication, and integration.----  Sponsor Links:🔗 Explore the 2026 ​Deloitte Human Capital Trends Report🔗 Learn more about SixFiftyMPL Links:🔗 Go sign up for MPL Build.----  (20:45) Joining Brex During a Company Pivot(21:20) Brex’s 2024 Year of Transformation(23:20) The January 1 Call: Capital One Acquisition Diligence Begins(25:05) Three Weeks to Diligence, Communications and Announcement(26:30) Late Nights, Diligence Requests and the Pressure to Be Accurate(28:00) Supporting Executives Through the Emotional Weight of the Deal(29:00) Communicating on Behalf of the CEO and Building Trust Across Leadership(32:45) Telling the Company About the Capital One Acquisition(33:35) The Two-Part Communication Plan for Employees(35:30) The Emotional Load People Leaders Carry During Acquisitions(36:35) Diligence, Communication, Retention and Advocating for Yourself(39:50) “Don’t Crush the Butterfly” and Protecting What Makes Brex Special(43:15) How CPOs Should Advocate for Themselves During M&A(45:40) Fairness, Expectations and Protecting the Value of the CPO Role(49:15) Relaunching Brex’s EVP and External Story(50:35) The Story Behind “Be The Founder of Your Career”(53:10) The Foundry and Investing in Future Founders Inside Brex(57:48) Heather’s Superpower Nickname: Chief Truth-Teller Officer---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Patsy Mangan joined us on The Modern People Leader. We talked about Scribd Flex, why flexibility only works when it is paired with clarity and accountability, and why Scribd needed the GRIT Performance framework.----  Sponsor Links:🔗 Learn more about SixFifty🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Learn more about Beqom at beqom.com/mplMPL Links:🔗 Go sign up for MPL Build.----  (10:00) The Pandemic, Distributed Hiring and the One-Way Door(12:40) Creating Scribd Flex Instead of Choosing a Generic Remote or Hybrid Label(19:05) Learning That Flexibility Alone Does Not Create Connection(20:00) Designing Hub Days Around Concentration of Attendance(22:50) Why Scribd Flex Needed the GRIT Performance System(23:35) Visibility Does Not Equal Performance(24:10) Why Clarity Drives Accountability in Flexible Work(26:35) The Four GRIT Dimensions: Goal-Oriented, Results-Driven, Innovative and Team-Focused(28:10) Giving Employees Ratings Across Each GRIT Dimension(29:00) How Scribd Flex Gives Freedom and GRIT Gives Clarity(34:15) Why Scribd Made Performance More Complex, Not Less(36:05) Calibration, Manager Bias and Making GRIT Fair(38:40) The Next Big Evolution: Becoming AI-Native(40:05) Moving From AI Adoption to Workflow Redesign(41:00) Rethinking Hiring, Career Journeys, Promotions and Performance Standards(42:15) Hiring for Specialty, Not Just Capacity(45:05) Connecting HR Tools to Where Employees Already Work(45:50) Why HR May Need Software Engineers Inside the Function(50:20) Why Human Judgment Becomes More Important as Output Gets Easier(52:38) Career Advice: Learn the Rules, Then Rewrite Them---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Brandon Roberts, leader of Talent Strategy and Workforce Transformation at ServiceNow, joined us on The Modern People Leader. We talked about how ServiceNow is redesigning HR for the AI era, why every role needs to be mapped for AI impact, and more.----  Sponsor Links:🔗 Learn more about Tilt at hellotilt.com/mpl🔗Learn more about Beqom at beqom.com/mpl🔗. Explore the 2026 ​Deloitte Human Capital Trends ReportMPL Links:🔗 Go sign up for MPL Build.----  (09:30) Creating ServiceNow’s Talent Strategy and Workforce Transformation Organization(14:45) How AI Supercharges ServiceNow’s Workflow Platform(21:50) Now Assist and the Productivity Shift in HR Operations(22:55) Why ServiceNow Reinvested AI Productivity Gains Instead of Just Cutting Costs(25:15) How AI Is Changing Software Engineering Roles(29:25) Building an AI Heat Map for Every Role in the Company(35:05) AI Control Tower, Usage Signals and Where to Invest Transformation Resources(36:45) Employee Works and the Agent Orchestration Layer for HR(38:30) Data Agent, Engagement Agent and Real-Time People Insights(41:00) The Reskilling Challenge for HRBPs Using AI-Powered Insights(43:25) People Strategists, People Technologists and People Scientists(47:30) Why Brandon and Jacque Built the ServiceNow AI Transformation Playbook(51:15) Why Companies Are Too Focused on Technology and Not Enough on Skills(52:05) Helping People Step Away From Their Work Identity as Roles Change---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.