From Founder to CISO: What Building Taught Me About Securing

William Yeack

When I stepped away from Member.buzz, I didn’t expect to end up in cybersecurity leadership. But looking back, it makes perfect sense. That chapter taught me how systems break, how people think, and how much effort it takes to build something resilient. Becoming a CISO wasn’t a career pivot as much as it was the next evolution of what I’d already been doing.

The Pivot

Running Member.buzz gave me a front-row seat to what happens when technology meets the real world. People tried to hack the platform constantly, which forced me to think about security in a practical way. I wasn’t just patching issues; I was learning how to design systems that could handle pressure.

When you’re building a product, it’s easy to get caught up in new features and functionality. Security often gets attention only after something goes wrong. What I learned early on is that it needs to be part of the plan from day one. You have to ask: If this breaks, can we recover? If we lose power, data, or access, what happens next?

Eventually, I realized the skills I had developed as a founder – troubleshooting under pressure, thinking systemically, and balancing idealism with reality – were exactly what companies needed in a security leader. Stepping away from Member.buzz wasn’t a failure. It was a turning point that helped me see where I could make the biggest impact.

The Work

My first CISO engagement dropped me into a company that had little structure around IT or security. There wasn’t even a clear list of what systems were running or who was responsible for them. I started by mapping everything out: business processes, hardware, applications, and data flows.

From there, we began to modernize. We moved systems to the cloud, transitioned the data center to a managed provider, and built redundancy so the business could continue to operate during a disruption. Then came the essentials: penetration testing, backup and recovery, and monitoring.

Over time, it became clear that our gaps were less about control and more about visibility. We had strong systems but no good way to assess risk or track compliance activities across teams. That’s what led me into GRC, where I helped establish automated frameworks using platforms like Vanta. I also led a FedRAMP 20x project, working closely with auditors to get all documentation and testing completed on time. It was detailed, demanding work, but it showed me how structure and process are what make security programs sustainable.

The Lessons

Security is about people as much as it is about technology. You can buy every tool on the market, but without communication and a culture that values it, none of it works.

I also learned that vendor sprawl is a real security risk. Each new tool introduces cost, complexity, and potential exposure. Simplifying your environment isn’t just about saving money; it’s part of a solid security strategy.

The biggest lesson, though, is that good security is about finding the balance between perfect and practical. It takes deep technical knowledge, strong organization, and the ability to communicate clearly with leadership. Those skills don’t always exist in the same person, but the CISO has to live in both worlds.

Looking Forward

These experiences have shaped how I approach technology and business today. Whether I’m building a new framework or helping a company mature its security posture, my goal is the same: to create systems that are strong, scalable, and adaptable.

That mindset is also what led to YGI Solutions. What started as a focus on secure design has grown into a mission to help companies run better, safer, and smarter. Security, compliance, and efficiency aren’t separate priorities. They are all part of building something that lasts.

Comments

To add a comment, please login or register.

Related

C-Level Security: Bank security and the egg timer (how good management trumps technology)
The development of technology for securing information has been advancing at a pace that is truly astounding. In 20 years the security industry has evolved from Sun Micro Systems' Sunscreen and the Cisco PIX (yes I know there were a few others) to over a thousand security products of which nearly 700 are currently VC funded. All are trying to generate business from within this ever advancing market currently called Cyber Security. There are few tech markets growing at the rate of Cyber Security and as a result we are seeing investors, in a near desperate attempt to gather slivers of this market, throwing money at companies with Rube-Goldberg-inspired technology. We now have a flood of technology solutions that no one person can understand and the customers that consume this technology struggle daily with supporting and operating these systems. Many of the C-Level executives reading this may want to consider a management solution for the next expensive problem your engineering team presents to you.
C-Level: Fan Boy, XEB
In 1999 I was extremely busy. I had just started a company, my second, in the Network Security field which was new and unknown. Sales were slow, hacking was deep, deep inside campuses like Stanford and MIT and was considered sport. I was getting traction with banks and was in SF for a meeting. I remember walking down Mission past a guitar shop and hearing this song, guitar was hitting the tonic breaking into cool background riffs, a little vocal falsetto opening then breaking into verse…..broken and then back…..WTF. Reminiscent of a Cello piece I know……..inspired….. I stopped dead in my tracks - stunned. Who are these guys!?!
C-Level Security: When your team uses military analogies, are they using the wrong narrative?
For years, I have bristled when people would use medieval military descriptions in an attempt to convey concepts within the Network Security business. Bastions, Firewalls, Moats, Drawbridges, Countermeasures; all of these descriptions give way to a more accurate and detailed explanation of what was really taking place.
What to Say to the C-Level, get your security project funded today!
In near every business adding costs to Information Systems will be seen, by the people running the business, as a cost first, benefit second. Remarkably this still holds true despite a constant pulse of security events hitting the C-Level desks. So let's, as security professionals, develop an understanding of the C-Suite and the C-Levels as to their priorities.