Cynthia Hayward: From Headlines to Head of IT Risk

Get to know Cynthia Hayward and learn more about her unique journey to becoming our Director of IT Risk. 

Q: What did you study in school? Did you always plan to work in IT Risk? 

A: Not at all. I actually started out in journalism. I studied English in college, loved writing and spent my early career as a newspaper reporter. But when the industry shifted in the early ’90s, I decided to take a different path.

That led me to teaching English in China, earning my MBA and eventually stepping into financial services. From there, my journey moved through online banking, fraud investigations and, ultimately, IT risk.

Q: How did you make the jump from marketing into risk management?

A: It wasn’t a planned move—it came from curiosity. While working on digital banking products at Citibank, Bank One and Discover, I saw fraud becoming a bigger issue. Investigation teams needed help analyzing digital data, and I stepped in.

I loved it. It felt like journalism again—digging into details, piecing together a story and uncovering the truth. That experience sparked a whole new career direction.

Q: What prepared you for leadership in cybersecurity?

A: Deepening my expertise. I earned a master’s degree in computer forensics and my CISSP certification. It allowed me to grow from investigator to leader, shifting from responding to fraud to preventing it.

Q: What’s your philosophy as Enova’s director of IT risk? How do Enova’s values guide your leadership?

A: Engagement comes from involvement. My team always invites feedback when rolling out new initiatives. We believe the best expertise might come from someone closest to the process, someone with a broader perspective, or even from an outside view.

Bringing those voices together makes the work challenging, collaborative and exciting.

One of Enova’s core values, Best Answer Wins, really resonates with me. I’ve seen the right solution come from anyone, regardless of title or background. When everyone is engaged and respected, we get better answers and stronger results.

Q: How do you measure success?

A: Of course, we track risks mitigated and audits completed. But another important measure is culture. I know we’re succeeding when colleagues across Enova proactively factor security into their decisions and reach out with questions before finalizing plans.

Q: Looking back, what stands out most about your career path?

A: That it wasn’t linear. I went from chasing news stories to investigating fraud to shaping prevention strategies. What ties it all together is curiosity, critical thinking and resilience. Those traits opened doors I never imagined.