291 - HR Practitioner Turned Founder (On Thinking Like a CEO): Amit Rapaport (Co-Founder & CEO, Compete)

Deborah Yount, CHRO at Sutter Health, joined us on The Modern People Leader to share her journey from finance to leading HR at one of the largest healthcare systems in the U.S. We discussed how Sutter reduced turnover by nearly 40%, built a culture of leadership accountability, and scaled employee experience and development across 60,000+ employees.----  Sponsor Links:🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Learn more about Wellthy at wellthy.com/mplMPL Links:🔗 Go sign up for MPL Build.----  (05:18) Deborah’s Career Journey: From Finance to CHRO(08:15) Transition to Global Roles & Multinational Experience(10:31) Why Healthcare: Mission-Driven Work & Impact on Lives(11:21) Scale of Sutter Health: 60,000 Employees & Growing Network(14:57) Mission, Patient Experience, and Workforce Impact(16:22) Reducing Turnover from 18% to 9.8%: Key Results(17:46) Where to Start: Leadership, Culture & Employee Listening(19:06) Unique Challenges in Healthcare Workforce Experience(20:55) Differences from Tech: Purpose-Driven Work in Healthcare(22:00) “Power of One”: Bringing Thousands of Employees Together(24:32) Biggest Levers Behind Turnover Reduction(25:19) Fixing Early Attrition: Onboarding & Manager Enablement(27:40) Creating Career Pathways & Employee Growth Opportunities(28:00) Building a Development-for-All Strategy at Scale(30:52) Embedding Career Conversations Across the Organization(32:57) Leadership Modeling & Scaling Development Plans(33:35) HR Tech Stack, AI Integration & Learning Platforms---- 📬 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.

Eva Majercsik (Chief People Officer) and Trevor Schulze (CIO) at Genesys joined us on The Modern People Leader. We talked about how AI is reshaping how humans and machines work together, why CIO and CPO partnerships are more important than ever, and how to lead a human-centered AI transformation across the organization. ----  Sponsor Links:🔗 Book a conversation with Compete at compete.com/mpl🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Learn more about Wellthy at wellthy.com/mplMPL Links:🔗 Go sign up for MPL Build.----  (06:37) Shift from CFO Partnerships to CIO-CPO Collaboration(08:23) Evolution of the CHRO Role & Seat at the Table(12:26) The Changing Nature of Work & Culture Transformation(14:42) Why Collapsing CIO + CPO Roles is the Wrong Take(16:51) The Power of CIO-CPO Partnership as a Force Multiplier(17:49) How Eva & Trevor Actually Work Together Day-to-Day(21:34) Rethinking Org Design, Bots, and Workforce Structure(22:49) Redefining Success: KPIs, Incentives & AI Impact(25:26) Why AI Transformation is Not One-Size-Fits-All(26:24) From Strategy to Execution: Driving Cultural Adoption(27:07) “AI Unlocked” & Building AI Literacy Across the Company(29:33) Why You Shouldn’t “Boil the Ocean” with AI(31:48) AI Hype, FOMO & Leadership Pressure(32:06) Creating Psychological Safety & Responsible AI Adoption(35:33) What’s Actually Realistic in the Next 2 Years of AI(36:43) Human-Centered AI & Employees Owning Their Role Evolution(38:35) Will Everyone Become AI Power Users?(40:23) The Viral “AI Doomsday” Narrative vs Reality(42:46) The Massive Reskilling Challenge Ahead(43:34) Job Destruction vs Job Evolution & Creation(47:12) Why Curiosity & Growth Mindset Will Define Winners(47:54) The Most Important Skills: Curiosity, Judgment, Empathy(49:18) Abundance Mindset: AI Creates More Opportunity(51:15) Managing Fear, Emotional Load & AI Anxiety(52:58) Why Every CPO Needs a Strong CIO Partnership---- 📬 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.

Amit Rapaport, Co-Founder & CEO of Compete, joined us on The Modern People Leader. We talked about why most HR metrics don’t matter to your CEO, how to think like a CEO when looking at workforce data, and more.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/5-hr-rulesSponsor Links:🔗 Book a conversation with Compete at compete.com/mplMPL Links:🔗 Go sign up for MPL Build.----  (08:31) What Compete Does: AI Workforce Optimization Explained Simply(11:17) Why Most HR Metrics Don’t Matter to CEOs(14:47) Connecting Workforce Data to Business Outcomes and Revenue(17:34) Hiring Inefficiencies and the Hidden Cost of Poor Talent Decisions(18:03) Early Career Mistake: Reporting Data Without Strategic Context(21:30) From Executor to Strategic Business Partner in HR(22:33) Transitioning from HR Practitioner to Startup CEO(24:59) The Reality of Entrepreneurship: Feedback, Pressure, and Growth(27:14) Lessons from First-Time Founder Experiences and Challenges(29:03) How HR Leaders Can Think Like Their CEO(31:33) Aligning HR Metrics with Business Goals (Break-Even Example)(35:29) Upskilling, AI, and Driving Business Impact Through HR(37:24) Identifying High-Impact Employees and Productivity Signals(39:51) How AI Transforms Workforce Analytics(41:45) Human-in-the-Loop AI and Telling Better Data Stories(45:02) Security, Privacy, and Handling Sensitive Workforce Data---- 📬 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.

Beth Ley, Chief People Officer at Kendra Scott, joined us on The Modern People Leader. We talked about how to build the number one workplace for women, the “Great Talent Transfer” and Beth’s vision for internal talent mobility, and what it’s like to work with a visionary founder.---- Sponsor Links:🔗 Learn more about Wellthy at wellthy.com/mpl🔗 Learn more about Tilt at hellotilt.com/mpl----  (09:10) What Kendra Scott Stands For Beyond Jewelry(11:36) The “Great Talent Transfer” and Beth’s Vision for Internal Talent Mobility(14:33) How Beth Operationalizes Big Talent Ideas with Skills Inventory and Technology(17:31) Surprising Skills Discoveries and Unlocking Hidden Talent Across the Business(19:38) What “Head Scratcher” Meetings Are and How They Surface Important Issues(22:34) Helping Leaders Navigate Pressure, Change, and Economic Uncertainty(25:12) Why Leadership and Management Are Different and How Beth Leads Through Change(29:56) Fear, Loss, and Doubt: The Emotional Reality of Organizational Change(30:23) What Beth Has Learned Working with Kendra Scott’s New CEO(32:38) Beth’s Advice for People Facing Career Uncertainty and Reinvention(36:15) What It’s Like to Work with a Visionary Founder Like Kendra Scott(39:43) How Big Ideas Get Operationalized at Kendra Scott(41:30) Kendra Scott’s Commitment to Women’s Entrepreneurial Leadership(45:48) Beth’s Bigger Vision for Mentorship, Legacy, and Expanding Impact(47:12) Beth’s View on the Future of Retail, Human Connection, and Transformation---- 📬 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.

Matt McFarlane, Founder of FNDN, joined us on The Modern People Leader. We talked about how to build a successful HR consulting business, why niching down and strong branding matter, and how to create sustainable growth through content, community, and a portfolio career.----  Sponsor Links:🔗 Book a conversation with Compete at compete.com/mpl🔗 Learn more about Tilt at hellotilt.com/mplMPL Links:🔗 Go sign up for MPL Build.----  (05:07) Matt’s Career Story: From In-House HR to Founder of FNDN(08:03) Why Compensation Became Matt’s Core Focus Area(11:34) Taking the Leap: Leaving In-House and Starting from Scratch(12:09) Early Validation: Talking to Customers Before Selling(15:59) Finding a Niche: From Broad HR to Focused Compensation Services(17:19) The Importance of Customer Research and Feedback Loops(20:17) Building a Brand That Stands Out in HR Consulting(23:51) First Clients: How Matt Landed His Initial Work Without Cold Outreach(27:09) Using LinkedIn and Content to Build Trust and Generate Inbound Leads(30:00) Pricing Your Services: From Salary Goals to Hourly Rates(36:49) Overcoming Imposter Syndrome and Charging What You’re Worth(41:18) The Challenges of Going Solo: Isolation and Losing Team Dynamics(43:04) The First Invoice Moment and Early Wins as a Founder(44:58) Reflecting on Growth: Building a Business and Lifestyle by Design(48:22) From Consulting to a Portfolio Career: Expanding Beyond Time-for-Money(50:28) Launching a Podcast and Newsletter as Growth Channels(52:26) Creating Startup People Summit: Building Community and Events(54:20) Lessons from Running Events and Building in Public(56:44) Brand Playbook: Intentionality, Consistency, and Differentiation(01:01:31) Where to Find Matt and His Work---- 📬 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.

Most benefits strategies fail for one simple reason: employees don’t know how to use them. Matt Scovil, Co-Founder and CEO of Medefy, joined us to break down why confusing benefits lead to higher healthcare costs, why behavior change is the real unlock, and how HR teams can turn benefits from a cost center into something employees actually use.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode288Sponsor Links:🔗 Learn more about Wellthy at wellthy.com/mpl----  (09:18) Matt’s Origin Story(14:03) Why Health Benefits Are So Hard for Employees to Understand(19:47) How Benefits Complexity Exploded Over the Last 5 to 10 Years(25:07) What HR Leaders Should Do When Benefits Costs Feel Out of Control(32:58) How Medefy Discovered What Employees Actually Want from Benefits Support(37:21) The Biggest Pitfalls Employers Make in Benefits Design and Communication(42:04) How Preventive Care Incentives Can Dramatically Lower Healthcare Costs(43:17) What Real Savings Can Look Like When Employees Use Benefits Better(44:57) Where Benefits, Personalization, and AI Are Headed Next(54:20) One Action HR Leaders Can Take Right Now to Start Fixing the Problem(57:13) Rapid Fire: Advice for Someone Starting Their Career Today---- 📬 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.

Alex Coonce (Chief People Officer) and Patrick Quigley (CEO) from Sidecar Health joined us on The Modern People Leader. We talked about building a strong CEO–CPO partnership, why culture must scale before headcount does, and how companies can become AI-native while staying transparent with employees.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode287Sponsor Links:🔗 Learn more about Wellthy at wellthy.com/mpl🔗 Book a conversation with Compete at compete.com/mpl----  (06:17) How Alex joined Sidecar Health and the early hiring story(10:46) What Sidecar Health does and how their healthcare model works(16:52) The CEO–CPO partnership and how they built trust working together(17:57) Early disagreements, culture decisions, and navigating leadership dynamics during COVID(20:35) How Patrick’s expectations of the CPO role evolved beyond traditional HR(25:27) Frameworks for understanding the business: market, business model, and leadership dynamics(28:54) Decision-making: when the CPO leads vs. when the CEO steps in(31:32) Building a culture of ownership: “give speeding tickets, not permission slips”(32:25) Navigating uncertainty and employee trust during constant change(34:51) Leading the “people business” alongside the company business(39:53 Leadership changes and how to bring teams along during major org shifts(42:43) Managing leadership transitions and the “Olympic team” mindset for executives(46:43) AI strategy and preparing the organization for the AI era(48:24) Building an AI-native culture through experimentation and tool adoption(50:33) Why AI adoption was driven culturally through the people team, not just engineering(52:30) Operating lean: scaling a company without adding as much headcount(55:03) Rethinking career growth when management roles are fewer in the AI era(56:31) Curiosity, experimentation, and the future of AI adoption in organizations---- 📬 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.

Kim Smith from Tilt joined us on The Modern People Leader. We talked about how personalized leave support creates a better employee experience, what managers and HR teams often miss during leave transitions, and how to build a modern leave process that balances compliance, communication, and care.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode286Sponsor Links:🔗 Learn more about Tilt at hellotilt.com/mplMPL Links:🔗 Go sign up for MPL Build.(05:43) Kim’s Career Story: How Her Own Leave Experience Led Her into Leave Management(10:16) Life on a Two-Person People Team at Tilt(11:02) What Tilt Actually Does: Explaining Leave Administration in Plain Language(12:26) Why Great Leave Experiences Need to Be Personalized, Not Checklist-Based(16:29) The Two Types of Employees Who Show Up During Leave(18:35) What Employees Should Ask Their Manager Before Going on Leave(25:14) A Step-by-Step Walkthrough of Designing a Great Leave Experience(31:15) Kim Reflects on Her Own Leave Experience While Working at Tilt(34:46) Why Knowledge Transfer and Coverage Planning Matter So Much Before Leave(36:15) Why HR Often Resists Personalized Leave Support and How to Rethink It(39:51) How Kim and Janisa Designed the Employee Leave Experience at Tilt(41:59) The “Rule of Five” for Helping Employees Re-enter After Leave(44:30) Balancing Tech and Human Support in Modern Leave Management(47:11) How AI Can Help HR Teams Manage Leave More Effectively---- 📬 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.

Melissa Theiss, Head of People Ops at Kit, joined us on The Modern People Leader to break down how HR leaders can build real business acumen using practical frameworks like Track-Racehorse-Jockey, her PeopleOps maturity diagnostic, and a 90-in-90 listening tour. We also walked through how to turn employee feedback into an actionable backlog and use it to shape a people strategy that supports the business first while staying people-centric.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode285Sponsor Links:🔗 Book a conversation with Compete at compete.com/mpl🔗 Learn more about Wellthy at wellthy.com/mpl🔗 Learn more about Tilt at hellotilt.com/mplMPL Links:🔗 Go sign up for MPL Build.----  Timestamps:(06:51) Melissa’s career path(10:16)Melissa’s work outside Kit and her newsletter, The Business of People(11:45) what Kit does and how MPL uses it(14:50) “How does the business make money?”(15:20) Track-Racehorse-Jockey and how VCs evaluate a business(15:34) Track: market context and competitive landscape(17:56) Racehorse: business model and revenue engine (product-led growth, pricing, AI credits)(19:17) Jockey: leadership team signals and what to assess(20:18) Coaching HR leaders through business jargon and discomfort(22:59) Learning business acumen: newsletters, courses, and choosing an industry you care about(25:21) PeopleOps maturity diagnostic and how it works(25:44) The PeopleOps maturity score, priorities, and avoiding “too much process too early”(29:14) Example areas: compensation philosophy, interview structure, compliance, global workforce basics(31:13) How Melissa built the diagnostic over time(34:05) How often to re-run the diagnostic and keep improving over quarters(37:49) Managing feedback like a product backlog(44:38) Listening tours and what leaders uncover that surveys miss(48:44) The “90 and 90” listening tour structure, questions, and how to scale it past 100+ employees(53:33) Honesty in 1:1s and the value of quieter, thoughtful feedback(54:24) Building a cohesive people strategy from the three inputs(55:27) Weighting trade-offs and why “people-first” can fail if the business is not healthy---- 📬 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.

Jessica Zwaan joined us on The Modern People Leader for MPL Build’s first-ever AMA, alongside Jalene Vandermey-Jackson from Workleap. We talked about what traditional HR mindsets must be let go to become builders, how to collect lightweight employee feedback to help build the right products, and more.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode284Sponsor Links:🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Try AskChartHop at ChartHop.com/AI🔗 Learn more about Wellthy at wellthy.com/mplMPL Links:🔗 Go sign up for MPL Build.---- 📬 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.