What does a former choker setter in the Washington woods have to do with leading one of the country’s largest healthcare technology companies? More than you might think. Bill Miller (see bio below), Chairman and CEO of WellSky, shares a career journey that started far from the executive suite: growing up in a big Midwest family, running a paper route at seven years old, chasing football dreams, getting injured, and unexpectedly spending a summer in Washington working one of the most dangerous jobs in the country. His logging crew called him “Flatlander,” hid his horse, and gave him the kind of life lessons that do not show up in most MBA programs. From there, Bill’s path took him from Capitol Hill to urban planning, early internet startups, Cerner, OptumInsight, and eventually WellSky, where he has helped transform the company into a healthcare technology leader serving more than 20,000 clients across acute, post-acute, and community care. We talk about: • Why work ethic started early, with a paper route before sunrise • The summer as a Washington “Flatlander” that changed his perspective • What startups taught him about risk, resilience, and eating what you kill • His front-row seat to the early internet boom in Kansas City • What he learned at Cerner and Optum about scale, healthcare, and leadership • How WellSky grew from a struggling 400-person company into a 3,200-person platform • Why culture, communication, and mentorship matter even more as companies grow • How AI is reshaping healthcare technology and changing what is possible Bill also shares candid thoughts on leading through COVID, bringing people back to the office, building culture intentionally, and why he still attends new-hire onboarding sessions to stay connected to the people joining WellSky. This is a conversation about grit, timing, technology, leadership, and building something meaningful without forgetting where you came from. And yes…we also cover paper routes, Porsche road trips, hidden horses, and why sometimes the best leadership development program is surviving a summer with lumberjacks. This episode is brought to you by... Ever wish your company updates could be less "quarterly earnings report" and more "late-night talk show"? At Pelaccio & Partners, we're revolutionizing internal communications with podcasts that employees actually want to listen to. Imagine podcast episodes that make your employees laugh while staying informed. Our founder, Jeff Pelaccio, doesn't just create podcasts; he creates conversations that break through the noise. Whether you're a growing startup or a massive corporation, we turn your company's story into audio gold. Leadership becomes human. Remote teams feel connected. Your message cuts through the clutter. Jeff is happy to share his insights on improving your culture, increasing employee engagement, and retention. You can contact him via LinkedIn or schedule a Zoom call via this link - 15-minute call with Jeff. About Bill: Bill Miller is the Chairman and CEO of WellSky, one of America’s largest and most innovative healthcare technology companies, serving more than 20,000 clients across acute, post-acute, and community care. With more than 25 years of experience in healthcare technology, Bill has built a career around growth, innovation, and leading companies through meaningful transformation. Since joining WellSky in 2017, he has guided the company into new markets, overseen more than 14 strategic acquisitions, and helped establish the WellSky Foundation. Before WellSky, Bill served as CEO of OptumInsight, where he helped drive major revenue growth and expanded the company’s position in healthcare analytics. Earlier in his career, he held senior leadership roles at Cerner Corporation, with global responsibility for managed services, outsourcing, and technology services. Bill is a University of Kansas graduate and currently serves on the boards of Lyric and the WellSky Foundation.