As Chief Information Security Officer (CISO) at Paychex, Bradley Schaufenbuel has set the standard for how leading organizations should approach cybersecurity, elevating the practice from a technological function to a strategic business driver. During his tenure as CISO at both Paychex and Paylocity, Bradley has pioneered the integration of security into core business strategy, using his unique combination of legal expertise and technical knowledge to reshape how enterprises view and leverage their security investments. His approach has proved transformative — demonstrating how robust security can serve as both a business enabler and a competitive differentiator in today’s increasingly digitalized landscape.

In our recent conversation, Bradley shared his insights on building effective security teams, driving innovation in application security, and transforming the role of the modern CISO. Drawing from his experience leading security across crisis management, engineering, and application security teams, Bradley offers a blueprint for security leaders looking to create lasting business impact at scale.

Bridging Law and Technology

The functionality of security leadership has transformed dramatically over Bradley’s nearly three-decade career. “The elevation of security leaders to executive officers was a game changer,” Bradley said. “Prior to 10 to 15 years ago, security leaders were buried somewhere deep in the bowels of IT with no board visibility. Representation matters.”

This shift mirrors Bradley’s journey from technical practitioner to business executive. “Technical skills are important early in your career when you’re trying to prove that you have the knowledge needed to do the job,” he said. “I obtained most of my technical certifications earlier in my career when demonstrating technical competence was critical. I went to law school later in life, not to become a lawyer, but to learn how to think like a lawyer.”

Thinking like a lawyer proved invaluable as Bradley moved into executive leadership, shaping how he approached the complexities of running a company. “In law school, you develop skills around reasoning, comparative analysis, and logical persuasion. You learn how to make compelling arguments,” he said. “These skills are essential in the C-suite and I’ve used them to become a more effective senior leader.”

That perspective has given Bradley a differentiated lens on what a CISO’s top priorities should be. “The CISOs that succeed today are more business savvy than they are technical experts,” Bradley said. “As a security leader, you must change the way you think to obtain and keep a seat at the executive table. At that level, you’re no longer just the advocate for security, and your job is not just to stop cyber-attacks. You need to enable your business to succeed in the marketplace and help the business differentiate itself from the competition.”

Building Diverse Security Teams

Bradley has developed clear principles that guide how he builds and develops security teams at Paychex. His approach emphasizes blending experience levels and fostering an inclusive environment that drives innovation. 

“Use a mix of veterans and newbies,” he said. “The newbies are grateful for the opportunity, bring fresh ideas, and learn from the veterans. The veterans enjoy mentoring the up-and-comers.”

According to Bradley, diversity plays a crucial role in team effectiveness. “Encourage diversity in hiring and then engrain inclusivity to retain diverse talent,” he said. “Research shows that diverse teams are more innovative. Don’t stymie your team’s effectiveness with groupthink by hiring people that look and think like you.”

This philosophy extends to how Bradley structures security operations and melds with his background as a Six Sigma Black Belt to shape his management approach. “I leverage Six Sigma principles for managing all security operations,” he said. “That means focusing on the needs of stakeholders, mapping the value stream of all security activities, eliminating non-value-adding steps, listening to the people involved in the process, using a structured approach to analyze and reduce the causes of variation, and using the results of that analysis to further improve the process.”

The rapid evolution of technology, particularly in cloud computing and artificial intelligence, has influenced how Bradley thinks about building security teams as well. “When you’re initially building out a security organization, you need a few security generalists or ‘jacks of all trades,'” he said. “There’s not a lot of opportunity for specialization at this point. You just need people who understand the basics of security and are proficient enough in technology to apply those across multiple technical domains.”

Navigating The Future of Application Security

As technology changes at an ever-increasing pace, an organization has to keep up with its approach to application security. Bradley recently wrote about application detection and response (ADR) and its potential to shift security from reactive to proactive strategies. “I wrote that article four months ago, and only a couple of months after the concept of ADR had even emerged,” Bradley said. “This evolution in the space has influenced our own application security strategy. What’s the point of being a thought leader if you don’t adopt your own theories in practice?”

Bradley sees new challenges emerging as applications become increasingly distributed. “One of the enemies of security is complexity,” he said. “The more complex a system is, the more difficult it is to secure it. As applications become more distributed, they become increasingly complex and thus harder to secure. Also, the more distributed an application is, the larger its attack surface is. A larger attack surface is always going to be more difficult to secure.”

That security-first mindset, coupled with Bradley’s first-hand experience advising security startups, help him evaluate potential vendors for Paychex. “Two of the reasons why I advise startups is to gain early access to the most innovative cybersecurity technology, and to shape the development of this technology to specifically serve the needs of me and my peers,” he said. “When I’m evaluating new security vendors for my employer, I look for some of the same things that I look for in a startup I might advise, which is innovative technology, a better way of accomplishing something than what’s out there, and a willingness to work with us to understand how to better meet our needs.”

Security as Strategic Value

Bradley’s legal background gives him unique insight into the intersection of enterprise security and regulatory compliance. “My legal background helps me translate legal and regulatory language into practical technical requirements,” he said. “Philosophically, I see legal and regulatory requirements as a baseline for technical controls. Any security controls that exceed this baseline are discretionary.”

That angle shapes Bradley’s worldview on security investments and risk management. “Any controls that exceed applicable legal and regulatory requirements should be implemented based on cost-effective risk reduction,” he said. “In simpler terms, I start by doing what I have to do, and then choose what to do above and beyond that based on risk-based return on investment.”

Managing security during acquisitions presents its own challenges, and Bradley has crafted a set of principles that allows him to find value in potential business deals for his company. “Understand the security posture of the target as soon as possible, preferably before the deal closes,” he said. “I’ve been able to negotiate a more favorable deal price based on unearthing cybersecurity risks that were previously undisclosed.”

Bradley emphasized the importance of working effectively with security teams during transitions, as well as creating realistic expectations. “People are what make a security program effective. Treat the security professionals at the target well,” he said. “They know where the ‘bodies are buried’ and will be key to helping you extend your security program to the target’s environment. Plan for ample transition time post-close. It’ll take longer than you expect to integrate two different organizations and security programs. However long you think it should take, double that.”

Redefining the CISO Role

As the role of CISO continues to evolve, Bradley sees opportunities for security to drive business growth directly. “The time of the CISO as a business leader is already upon us,” he said. “The next stage of this evolution is where the CISO becomes a driver of top-line revenue growth. The most successful CISOs will be those who find ways to leverage security to differentiate their business offering, or who bring cybersecurity products or services to market on behalf of their organization.”

He’s already put this philosophy into practice at Paychex. “For example, my company offers a variety of HR software and services to small businesses,” he said. “I worked extensively with our strategic partnership team to enter into a partnership with a cybersecurity service provider to offer multiple security services to our small business customers. Cybersecurity has become a revenue generation engine for my company, not just a cost center.”

For aspiring security leaders, Bradley emphasized the importance of developing broad business acumen. “CISOs are required to oversee all security domains,” he said. “To position yourself well for a security leadership opportunity, look for opportunities to gain experience in multiple security domains. Learn business skills outside the security domain. CISOs have P&L responsibilities. Learn the basics of finance. Know the differences between a capital expenditure and an operating expenditure. Understand depreciation.”

Looking ahead, Bradley hopes to see more CISOs take on board roles, and in kind, more discussion of their importance on boards. “As more CISOs transition from technical leaders to business leaders, there’s a lot of value in having CISOs serve on boards. Besides my own articles on the topic, I’m not seeing much written about this topic right now.”