287 - How This CEO–CPO Duo Is Preparing Their Organization for the AI Era: Alex Coonce & Patrick Quigley (Sidecar Health

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.

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Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode287

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(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

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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.