Rich Bailey

What motivated you to pursue another master’s degree, and what specifically drew you to the MCiM program? 

I’ve spent over 20 years at the chaotic, often messy, intersection of healthcare, technology, and operations, and I realized something: digital transformation isn’t just about fancy tools—it’s about people, leadership, and knowing how to drive real change. I pursued MCiM because I wanted to level up, not just in technical expertise, but in how to actually get things done in complex healthcare environments. This program brings together all the pieces—business strategy, digital health, leadership—all wrapped up in a community of insanely smart and passionate people. It was a no-brainer.

I also knew it was the right time for another master’s degree because when I completed my first one over a decade ago, I was in a much different place—both personally and professionally. Healthcare has evolved so much since then, and so have I. Over the past seven years in leadership, I’ve craved an education that truly capitalized on my passion for technology and the healthcare space. MCiM was the perfect fit, bridging my experience with the cutting-edge knowledge and strategic thinking I need to lead in this rapidly changing industry.

You stepped into a new leadership role while in the program. How has MCiM supported your professional growth?

MCiM has been like a real-time leadership bootcamp—except instead of just theory, I’ve been applying it immediately in my role. Stepping into the interim Associate Chief Information Officer position while in the program has meant navigating major challenges, from leading digital transformation efforts during our Epic migration to ensuring our Health IT experts feel supported and empowered to drive meaningful change in healthcare—all while keeping our patients at the heart of everything we do. The program has provided me with the frameworks, mentorship, and confidence to take on these challenges head-on. And being surrounded by innovative and amazing classmates who are also out there making moves? That’s been just as transformative. Iron sharpens iron.

Can you share a specific example of how MCiM has strengthened your confidence and leadership approach?

One of the biggest lessons I’ve taken from MCiM is how to navigate high-stakes decision-making with confidence. A key moment for me was stepping into the role of interim Associate CIO at San Mateo County Health. Suddenly, I wasn’t just influencing strategy—I was leading it. From day one, I had to make tough calls, align stakeholders, and push forward digital initiatives that impacted thousands of patients and staff.

Through MCiM, I gained the tools to handle these challenges head-on. Whether it was enhancing my skills on managing resistance to change, sharpening my executive presence, or leveraging data to drive buy-in, the program gave me the confidence to not just step into leadership, but to own it. More importantly, it reinforced that leadership isn’t just about making decisions—it’s about inspiring trust, driving meaningful progress, and creating an environment where people can thrive.

How do you plan to leverage your MCiM experience to drive meaningful change in healthcare and digital innovation?

Healthcare is drowning in inefficiencies—fax machines are still in use, workflows are tangled, and providers spend more time battling technology than leveraging it to improve care. I want to change that. My goal is to harness digital health and AI-driven solutions to streamline workflows, reduce administrative burdens, and enhance patient outcomes. Whether it’s revolutionizing the referral process (seriously, why are we still faxing?) or making care coordination truly seamless, I’m committed to driving meaningful change.

But real transformation isn’t just about technology—it’s about building systems that work for people, not against them. MCiM has reinforced my belief that innovation isn’t just about disruption; it’s about sustainability, equity, and impact. The program has given me the strategic lens and technical knowledge to bridge the gap between vision and execution. Now, as I apply for healthcare executive roles, more specifically the Chief Information Officer role at San Mateo County Health, I feel more prepared than ever to take on the challenge of being an executive in the healthcare world. A year ago, I might have hesitated to put myself forward, but MCiM has given me the confidence to step up, lead boldly, and help shape the future of healthcare.