The Modern People Leader: Forward-Thinking HR

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/episode288
Sponsor 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/episode287
Sponsor 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/episode286
Sponsor Links:
🔗 Learn more about Tilt at hellotilt.com/mpl
MPL 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/episode285
Sponsor 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/mpl
MPL 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/episode284
Sponsor Links:
🔗 Learn more about Tilt at hellotilt.com/mpl
🔗 Try AskChartHop at ChartHop.com/AI
🔗 Learn more about Wellthy at wellthy.com/mpl
MPL 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.