Cybersecurity changes every day. Every time technology takes one step forward, it’s accompanied by increased vulnerabilities that companies need to be aware of and plan for. That’s why we sat down with WorkWave’s Chief Information Security Officer, Nathaniel Cole, to discuss some key issues facing service businesses today. We sat down with him to discuss his approach to security and some key issues facing businesses today.
A: My background of experience spans application security, fintech and banking, B2B payments and more. While cybersecurity should be a priority for every business in any industry, digital security is of utmost importance in these areas because it directly impacts customer trust and data. I’ve had first-hand experience in offensive security and ransomware recovery, and I’m excited to help apply this experience to help WorkWave continue to build and improve our security posture.
When it comes to my approach to security, I tend to put information security leadership into two main camps: those who maintain existing systems and those who actively build and improve them. While there is a mix of both in any security posture, I firmly align with a builder mentality. I consistently look for ways to enhance security capabilities, design more effective controls and implement measures that make a tangible difference.
What excites me about being part of the WorkWave team is the opportunity to bring this builder approach to benefit our customers. The technologies that malicious threats are using are evolving quickly, as are the technologies our customers are using to run their businesses. Knowing threats are always changing, trust is a key component of our security program at WorkWave. That means understanding the real-world threats we face, being honest about our capabilities and continuously working to close any gaps.
A: When I talk about security posture, I’m referring to an organization’s overall security strength and readiness. It covers everything from how well you prevent unauthorized access to how quickly you can detect and respond to potential threats. A company’s security posture reflects your technical controls and your processes, your people and your overall approach to managing security risks.
Think about security posture as the security foundation of your business. It’s built on how effectively you handle everyday security tasks—keeping systems updated, managing who has access to what, identifying vulnerabilities before they can be exploited and having plans in place for if something goes wrong. All these elements work together to determine how resilient your organization is against various security threats.
Many security professionals use frameworks like the NIST Cybersecurity Framework to help structure and assess their security posture. These frameworks provide a common language and systematic approach to understanding where you stand and what you need to improve.
For our customers, a strong security posture means better protection for their data (and their customers’ data).
A: The NIST Cybersecurity Framework was developed by the National Institute of Standards and Technology to give organizations of all types a practical approach to managing security risks. I find this framework valuable in how it organizes security into five interconnected functions that work together in an ongoing cycle.
It works by first identifying what you’re trying to protect—your systems, data, users and other assets. Once you know what you have, you can implement appropriate safeguards to protect those assets from threats. But since no protection is perfect, you also need ways to detect when something goes wrong. When you do spot a problem, you need established processes to respond effectively. And, finally, you need plans to recover and get back to business after any incident.
What makes this framework so useful is that it’s adaptable to organizations of all sizes. I’ve seen both large enterprises and smaller companies use these principles to significantly improve their security without needing massive budgets or specialized teams.
A: There’s a common misconception that only large companies with valuable data are targets for cyberattacks. In my experience working across different industries, security incidents don’t discriminate based on company size or sector. Some would even argue that smaller businesses may tend to be more vulnerable than their enterprise counterparts, largely because of smaller resources for robust security frameworks. What many people don’t realize is that threat actors often aren’t targeting specific organizations at all; they’re scanning for known vulnerabilities and attacking companies using those systems. Every organization today relies on technology and data, which means everyone faces some level of risk.
Organizations of all types and industries often hold valuable information that attackers want. This could be customer payment details, employee personal information or even access to your systems that could be used as a stepping stone to reach other targets.
A: The rapid adoption of AI across all types of software has created both new challenges and opportunities in security. There are a couple of key trends that business leaders should pay attention to.
First, AI has significantly changed how we need to approach third-party due diligence. When using AI-powered software—whether it’s a standalone AI tool or a regular application that now has AI features—organizations need to ask different questions about security. How is your data being used to train models? What controls exist around that data? Who might have access to your information through these AI systems? Getting satisfactory answers to these questions is crucial for building trust that your information is being handled properly.
The second major shift involves risk ownership. As more organizations move their operations to the cloud and use third-party AI services, there’s been a fundamental change in who’s responsible for different aspects of security. When you trust someone else to run your infrastructure or process your data through AI systems, they take on a significant portion of that security responsibility.
At the same time, organizations need to be strategic about how they handle data in this new environment. For example, every time you download data from a secure cloud system to your local computer—say, as a CSV file—you’re potentially increasing your security risk. Keeping data within secure environments whenever possible is becoming increasingly important as AI makes data more valuable and potentially more vulnerable. This is a prime example of why it’s important to understand your security posture and that of the third-party vendors your business partners with, so that you thoroughly understand the best ways to keep your data safe and who is charged with the risk.
A: Yes, I am experienced with Red Team testing, which is a mix of automated and manual testing used to simulate real-world attacks against an organization’s systems and defenses. This way, a security team can identify vulnerabilities or configuration issues that could result in a security threat. It’s essentially a controlled version of what malicious actors might attempt.
This type of vulnerability testing provides a unique perspective that directly benefits our customers because it influences how we design our security controls. We’re constantly thinking about compliance and regulatory needs and then taking it one step further by asking questions like ‘How might someone try to bypass this protection?’ and ‘What’s the next move if this defense fails?’ It’s almost a version of exception-based reporting done in a very intentional, hands-on way that shows the impact of the deviation on the organization. It helps us prioritize security investments where they matter most and develop an approach that’s both practical and effective against the types of threats our users actually face.
Most malicious actors do not differentiate companies by size, vertical or technology footprint. What this means is that every company is likely being assessed for potential opportunities to steal data, impact operations to extort a payment or attain fraudulent payments. There are a few things every company could do to help lower the overall risk.
Nathaniel Cole is a cybersecurity executive known for a pragmatic, business-aligned approach to building and leading security programs. As a CISO at WorkWave, Cole focuses on protecting organizations by validating real-world risks, strengthening operational resilience and aligning security with business objectives.
Throughout his career, Cole has led ISO 27001:2022-compliant programs, guided companies through PCI DSS and NIST 800-171 requirements and built security foundations designed to scale with growth. He has responded to two ransomware incidents — managing network recovery for a Fortune 500 software company as a consultant and leading response efforts internally. Cole has also overseen penetration testing services to help organizations assess control effectiveness and identify vulnerabilities.
Cole believes effective security is rooted in validating risk, strengthening operational controls and enabling business innovation. He collaborates closely with technology, legal and business leaders to protect critical assets while supporting organizational growth.
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