Ryan Winn
CISO
AdventHealth
Ryan Winn is the CISO at AdventHealth, and he leads enterprise-wide strategies to protect their systems, data, and—most importantly—their patients. With over two decades of experience in healthcare IT, he is passionate about building resilient infrastructures that support clinical excellence and digital transformation. He thrives at the intersection of security and mission, helping ensure AdventHealth can deliver whole-person care with confidence and integrity.
A fun fact about Ryan, he originally majored in Mesoamerican Anthropology before moving into a more technical path.
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Give us a brief overview of the path that led to your current role.
I’ve spent my entire career in healthcare, serving in a variety of roles—from organizational development to corporate communications. Along the way, I discovered my passion for information technology, which ultimately led me to leadership roles as CTO, CISO, and CIO across multiple healthcare systems. I’m especially drawn to the dynamic challenges of cybersecurity and the high stakes it presents in today’s healthcare environment.
What is one of your guiding leadership principles?
A core guiding principle for me is that information security should be a strategic enabler, not a barrier. I believe in fostering deep collaboration across clinical, operational, and technical teams to align cybersecurity efforts with the organization’s broader mission and goals. By integrating security into the fabric of the business, we not only reduce risk—we also create the conditions for sustainable growth, innovation, and trust.
What is the greatest challenge CISOs face today, and how are you addressing it?
Healthcare is evolving rapidly through digital transformation and the growing use of technologies like AI, creating both new opportunities and complex cybersecurity challenges. As a CISO, I must balance the drive for innovation with the responsibility to protect critical systems and patient data. The expanding attack surface—from cloud adoption to AI-powered tools and connected devices—demands that cybersecurity be embedded early to enable secure, scalable growth. In this fast-paced environment, success depends on being a proactive partner to the business while maintaining resilience, agility, and trust.
What is the key to success for someone just starting out as a CISO?
For a new CISO, success starts with listening, mapping the landscape, and aligning with both business and technology leaders. You can’t secure what you don’t understand, that means knowing the workflows, mission, and human stakes. Building credibility early—through transparency, empathy, and early wins—paves the way for long-term influence and impact.
How do you measure success as a leader?
I measure success as a leader by how well I help others succeed and how effectively we achieve meaningful results together. If my team is growing, empowered, and operating with clarity and confidence, that’s a clear sign of leadership impact. I focus on creating an environment where people can do their best work—aligning their strengths with organizational goals. Ultimately, success means delivering outcomes that matter while developing leaders who can sustain and expand that success over time.
What is the value of being a member of Gartner C-level Communities?
I view this largely as a networking opportunity with people facing similar challenges.
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