The Modern People Leader: Forward-Thinking HR

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.
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🔗 Learn more about Beqom at beqom.com/mpl
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MPL Links:
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(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(23:45) Why Tenure and Title Are Outdated Proxies for Value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
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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.
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Sponsor Links:
🔗 Learn more about SixFifty
🔗 Explore the 2026 ​Deloitte Human Capital Trends Report
MPL Links:
🔗 Go sign up for MPL Build.
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(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
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📬 Subscribe to our weekly newsletter to get episode recaps
💡 Follow The Modern People Leader on LinkedIn
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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.
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Sponsor Links:
🔗 Learn more about Beqom at beqom.com/mpl
🔗 Learn more about SixFifty
MPL Links:
🔗 Go sign up for MPL Build.
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(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
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📬 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.
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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.
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(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
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📬 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 SixFifty
MPL Links:
🔗 Go sign up for MPL Build.
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(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.