The Modern People Leader: Forward-Thinking HR

Laura Tomaino, Chief People Officer at Glooko, joined us on The Modern People Leader. We talked about why “People-First” leadership feels harder in 2026 and what it actually looks like to live up to that today.
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(08:51) Building HR from Scratch at HealthEdge & Scaling Through Growth
(11:12) Joining Glooko & Leading People Across Seven Countries
(13:03) What Glooko Does & Supporting Diabetes Care Globally
(13:39) Joining Before a $100M Series F & Building a New Leadership Team
(15:15) Why “People-First” Leadership Feels Harder in Today’s World
(16:56) The Real Meaning of Being People-First in HR
(19:22) Why HR Leadership Can Feel Lonely & the Need for Real Conversations
(21:20) The Four Drivers of Employee Experience: Connection, Growth, Recognition & Alignment
(25:54) Why Mission Alignment & Business Transparency Matter
(28:08) Bringing Remote Teams Together Through Global Company Events
(29:09) How to Stay People-First Even on a Tight Budget
(32:02) Tough Leadership Decisions, Benefits Changes & Listening to Employees
(36:06) AI Anxiety, Flattening Organizations & the Future of Work
(38:24) Why Laura Is Optimistic About AI & Workforce Change
(42:40) How Employees at Glooko Feel About AI Adoption
(46:36) Curiosity Over Fear: What Makes Teams Thrive During Change
(48:15) Why Curious People Beat “Brilliant Jerks” Every Time
(51:28) Hiring for Curiosity, Passion & Human-Centered Thinking
(55:20) AI’s Future in Healthcare & Managing Massive Health Data Responsibly 
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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.

Jevan Lenox, Chief People Officer at Writer, joined us on The Modern People Leader. 
We talked about why AI adoption alone is not enough, how companies can use “directed innovation” to drive real business outcomes with AI, and what high performance looks like in the AI era.
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Sponsor Links:
🔗 Learn more about Cloverleaf at cloverleaf.me/mpl
🔗 Explore the 2026 ​Deloitte Human Capital Trends Report
🔗 Book a conversation with Compete at compete.com/mpl
MPL Links:
🔗Go sign up for MPL Build.
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(06:23) Reinventing McKinsey’s Hiring Process Across North America
(07:21) Moving to Asia-Pacific & Falling in Love with the People Path
(08:22) Leaving Consulting for High-Growth Companies
(09:03) Lessons From Square, Blue Bottle Coffee & Founder-Led Companies
(10:08) Why Blue Bottle Coffee Changed Jevan’s Perspective on Leadership
(12:55) What Writer Actually Does Explained in Plain Language
(14:40) The Disconnect Between AI Adoption & Real Business Outcomes
(16:10) Why AI Fluency Alone Does Not Create Business Value
(17:34) Why the Best AI Strategies Combine Bottom-Up & Top-Down Leadership
(20:06) AI’s Next Phase: Growth, Scale & Expanding the Business
(21:40) Marketing Personalization, AI Agents & Customer Experience at Scale
(23:35) Stephen’s CTO Experiments & Building AI Systems for MPL
(27:10) Directed Innovation vs “Let a Thousand Flowers Bloom”
(29:30) From AI Adoption Metrics to Real Organizational Outcomes
(31:05) Why AI Leaderboards Can Create the Wrong Behaviors
(32:22) Understanding AI Workflows, Iteration & Knowledge Sharing
(33:28) Positive Deviance & Finding High-Impact AI Use Cases
(36:10) AI Virality, Peer Learning & Spreading Better Workflows
(38:12) What High Performance Looks Like in the AI Era
(39:45) Why “AI-Pilled” Employees Become Force Multipliers
(41:18) System Thinking, Career Growth & Reinventing Performance
(42:05) Daniel’s AI Sales Bot & Reinventing Enterprise Sales Workflows
(43:18) Why Traditional Change Management No Longer Works
(44:15) “There Is No Final Answer in HR Anymore”
(45:20) AI as a Creative Thought Partner & Expanding Imagination
(46:08) AI, Productivity & Unlocking Strategic Thinking Time
(47:20) The “Maslow’s Hierarchy” of AI Value Creation
(48:10) The Rise of AI Managers & Automated Leadership Structures
(50:32) AI’s Impact on Early Career Talent & New Grads
(52:02) Why Adaptability Will Matter More Than Specialization
(53:32) Why Talent Acquisition & Recruiting May Be Fundamentally Reinvented 
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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
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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.

Kirsten Moorefield, Chief Strategy Officer & Co-Founder at Cloverleaf, Sarika Lamont, CPO at Vidyard, and Sarah Royer, Sr. Manager of People Ops at Nirvana Insurance, joined us on The Modern People Leader for a live discussion on AI coaching. 
We talked about what AI coaching actually means today, building these tools in-house versus buying, and why career growth will never be a perfect checklist.
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Sponsor Links:
🔗 Learn more about Intuit QuickBooks Payroll at QuickBooks.com/workforce
MPL Links:
🔗 Go sign up for MPL Build.
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(08:53) What AI Coaching Actually Means Today
(10:47) The AI Coaching Definition Problem & Human Coach Misconceptions
(12:01) Why AI Cannot Replace Human Relationships at Work
(13:54) AI as an Enabler for Better Manager Conversations
(15:05) Teaching Employees to Own Their Career Growth
(16:18) Building AI Tools for Managers, Coaching & Performance Conversations
(18:08) Connecting HR Systems, Context & Employee Data Together
(20:02) Sarah’s Approach to Building AI Coaching Skills in Claude
(22:01) Buying vs. Building AI Coaching Tools Internally
(24:05) Kinfolk, AI Employees & Workflow Automation at Vidyard
(27:00) Claude Skills, AI Coaching Gems & Legal Guardrails
(29:47) Why HR Teams Should Start Small & Experiment Fast
(31:00) What Makes an AI Coaching Tool Actually Valuable
(32:14) Why Daily Coaching & Relationship Context Matter Most
(34:11) The Importance of Personalized Coaching in the Flow of Work
(36:01) Cloverleaf’s MCP Approach & Integrating Behavioral Data
(37:12) Why Managers Struggle With Coaching Conversations
(38:04) HR’s AI Adoption Problem & Fear of Falling Behind
(40:07) Sarika’s Approach to AI Change Management at Vidyard
(42:02) Making AI Adoption Fun, Human & Transparent
(44:04) Focus Fridai, AI Enablement & Experimentation Culture
(45:12) Why AI Skills Are Becoming Mandatory for Employees
(46:09) Sarah on Creating Space for HR Teams to Build With AI
(47:53) HR Professionals as Builders & Full-Stack Problem Solvers
(48:49) AI Ethics, Compliance Risks & Responsible AI Coaching
(50:28) Balancing AI Pressure From CEOs While Protecting Employees
(51:15) Q&A: How Employees Are Actually Using AI Coaches
(52:43) Career Growth, Self-Ownership & the Limits of AI Guidance
(55:09) Why Career Growth Will Never Be a Checklist
---- 
📬 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.

Cara Brennan Allamano (Founder of PeopleTech Partners and former Chief People Officer at Lattice) and Jevan Lenox (Chief People Officer at Writer) joined Stephen at Fix Healthcare Live.
They talked about the growing pressure on HR leaders and why modern people leaders need to rethink how they operate in a rapidly changing world.
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Sponsor Links:
🔗 Explore the 2026 ​Deloitte Human Capital Trends Report
🔗 Learn more about Cloverleaf at cloverleaf.me/mpl
🔗 Learn more about Intuit QuickBooks Payroll at QuickBooks.com/workforce
MPL Links:
🔗 Go sign up for MPL Build.
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(03:00) How the CPO Role Is Transforming in Real Time
(04:00) COVID’s Lasting Impact on Employee Expectations and Healthcare
(05:00) Why Healthcare Became an Emotional Workplace Issue
(06:00) The Tension Between Rising Costs and Better Employee Support
(07:00) The Shift From an Employee-Powered Market to an Employer-First Economy
(08:00) Why Modern CPOs Are Starting to Look More Like COOs
(10:00) Business Acumen, Operating Acumen, and the New Expectations for HR
(11:00) Why Traditional Benefits Systems Are Falling Behind
(12:00) AI’s Rapid Growth and What It Means for HR Leadership
(13:00) How AI Is Democratizing Technology for People Teams
(15:00) Why Judgment and Expertise Still Matter in the AI Era
(16:00) The Case for Strategic Partners Over Building Everything In-House
(17:00) Scaling Better Employee Experiences Through AI Systems
(19:00) HR Leaders as Major Buyers of Healthcare
(20:00) The Ethical Weight of Benefits Decisions
(21:00) Why CPOs Need Innovative Healthcare Partners
(22:00) Making Hard Trade-Offs With Integrity
(23:00) Why Healthcare Innovation Feels Risky for Finance Leaders
(26:00) Cara’s Advice: Stay Educated on Emerging Healthcare Innovation
(27:00) Jevan’s Advice: Stop Searching for “The Answer”
(28:00) Why the Future of HR Requires Constant Iteration
(29:00) Community, Partners, and Navigating Uncertainty 
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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.

Lindsay Jurist-Rosner, Co-Founder and CEO of Wellthy, and Stephan Dolling, AVP of Global Benefits & Well-being at Merck, joined us on The Modern People Leader. 
We talked about the rising pressures facing working families and what companies can do to support their employees that are caregivers.
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Sponsor Links:
🔗 Learn more about Tilt at hellotilt.com/mpl
🔗 Learn more about Intuit QuickBooks Payroll at QuickBooks.com/workforce
🔗 Explore the 2026 ​Deloitte Human Capital Trends Report
MPL Links:
🔗 Go sign up for MPL Build.
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(06:00) HR’s Expanding Role in Healthcare & Family Support
(08:00) The Rising Cost of Childcare & Caregiving Challenges
(10:00) Layoffs, Workplace Pressure & The “Sandwich Generation”
(11:00) How Employee Expectations Changed Post-COVID
(13:00) Merck’s Philosophy on Supporting Working Families
(15:00) What Real Employee Support Looks Like in Practice
(17:00) Flexibility, Compassionate Time & Supporting Diverse Workforces
(18:00) The Importance of Benefits Communication & Employee Awareness
(20:00) Simplifying Access to Benefits Through Journey Mapping
(22:00) Most Popular Benefits at Merck: Backup Care, Flexibility & Concierge Support
(24:00) Why Backup Care Peaks During School Breaks
(25:00) Senior Care, Pet Care & New Caregiving Trends
(26:00) Why Managers Need Better Support & Empathy Training
(28:00) What Great Managers Do During Caregiving Crises
(30:00) Building a Workplace Culture Rooted in Flexibility & Trust
(31:00) The $70 Billion Childcare Disruption Problem
(32:00) How COVID Changed Merck’s Backup Care Strategy
(34:00) Why Fast, Flexible Care Solutions Matter Most
(35:00) The Future of Backup Care & AI-Powered Matching
(38:00) Why Employees Don’t Engage With Benefits Programs
(39:00) Simplicity vs Specificity in Benefits Communication
(41:00) Keeping Benefits Top-of-Mind Before Employees Need Them
(42:00) Using Employee Testimonials to Normalize Caregiving
(45:00) Why Modern Workplaces Need to Normalize Care Conversations
(46:00) Real Stories of Caregiving Support During Crisis Moments
(48:00) Helping Employees Through Dementia Care & COVID Emergencies
(49:00) Navigating Grief, Medical Debt & End-of-Life Care Support
(51:00) Building the Business Case for Caregiving Benefits
(53:00) Productivity, Flexibility & the ROI of Caregiving Support
(55:00) Why Caregiving Is an Economic Issue, Not Just a Social Issue
(56:00) AI, Productivity & the Cost of Context Switching
(58:00) Mental Health, Burnout & What Employees Need Most Right Now 
---- 
📬 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.