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Cybersecurity Awesomeness Podcast Recap - Episode 102: Insider Threats

Mar 24, 2025 12:17:40 PM

Welcome to the recap of the Enterprise Management Associates (EMA) Cybersecurity Awesomeness (CSA) Podcast. Hosted by Chris Steffen, Vice President of Research and Ken Buckler, Research Director at EMA, the CSA Podcast covers a wide range of cybersecurity topics, from cyber workforce talent shortages to cyber threat intelligence, to current events in technology and security. This short, laidback podcast is for listeners of all skill levels and backgrounds.

A pervasive issue looms large on the radar of IT practitioners and decision-makers: the insider threat. In the Cybersecurity Awesomeness Podcast, expert hosts Chris Steffen and Ken Buckler recently uncovered the intricacies surrounding this topic, framed through a real-world corporate espionage case that encapsulates the complexity of managing insider threats effectively.

The podcast delves into the essential question: what does insider threat truly mean, and how can organizations navigate this gray area without unintentionally exacerbating the problem? It is easy to associate insider threats solely with malicious intent, but as the discussion unfolds, we understand that this threat often manifests in ways that organizations might not expect. The story of Rippling, a company engaged in a tense rivalry with Deel, illustrates the depths to which insider threats can penetrate an organization’s security. An employee – who, on paper, was merely adding to the company’s human resources – was found surreptitiously collecting sensitive information from Slack, targeting topics that directly benefitted their competitor.[1] The violating behavior was not only a breach of trust, but also highlighted critical flaws in how organizations manage their internal security protocols.

What makes this case particularly compelling is how Rippling approached the situation. Rather than confronting the suspected mole directly, they devised a clever ruse involving a fictitious Slack channel called "D-Defectors," instantly turning the tables and unearthing the underlying corporate espionage occurring. Such a strategy not only exposed the spy, but also brought to light the inadequacies of trust and security inherent in corporate dynamics. Steffen and Buckler emphasized that the need for robust insider threat strategies cannot be overstated. The effectiveness of a security team often hinges on their ability to identify such nuanced threats early.

As organizations grapple with these complex scenarios, the dialogue around setting up solid insider threat programs becomes paramount. Steffen and Buckler outline the balance that needs to be struck: while it’s vital to implement safeguards, care must be taken to avoid creating a culture of mistrust among employees. After all, a certain degree of inadvertent snooping is almost a natural inclination within corporate environments designed for collaboration. However, when human nature intersects with cybersecurity, it demands an approach that is both strategic and sensitive.

The theme resonates throughout the discussion: insider threats are not just about technology, but also about fostering awareness and vigilance across all organizational levels. An additional layer of protection can be achieved through adopting methods such as microsegmentation of networks, reinforcing that robust cybersecurity is not merely about firing off security measures, but also about enabling proper access controls and fostering trust among teams.

For IT leaders considering how to prioritize their cybersecurity initiatives, this podcast offers invaluable insights. As they dissect the unfolding narrative of Rippling and Deel, they encourage decision-makers to assess the effectiveness of their current insider threat strategies. The conversation between Steffen and Buckler illuminates the necessity of clear policies, effective monitoring systems, and an empowered security team ready to tackle the intricate web of cybersecurity challenges and also the human elements that introduce vulnerabilities.

Listen to the full podcast for an in-depth exploration of these issues, along with engaging stories and pragmatically sound approaches to managing insider threats in today’s multifaceted cybersecurity climate. Moreover, for additional resources and insights, be sure to visit Enterprise Management Associates at www.enterprisemanagement.com. Your organization’s security posture could greatly benefit from the knowledge shared in this episode.

You can find the Cybersecurity Awesomeness Podcast at www.cybersecurityawesomeness.com. To gain deeper insights and hear firsthand comments from Chris and Ken on these vital topics, we invite you to listen to the full podcast. Furthermore, for more resources and expertise on cybersecurity, visit Enterprise Management Associates at www.enterprisemanagement.com.

[1] https://www.rippling.com/blog/lawsuit-alleges-12-billion-unicorn-deel-cultivated-spy-orchestrated-long-running-trade-secret-theft-corporate-espionage-against-competitor

Topics: Cyber Security

Chris Steffen & Ken Buckler

Written by Chris Steffen & Ken Buckler

Christopher Steffen, CISSP, CISA, is the vice president of research at EMA, covering information security, risk, and compliance management. Before EMA, he served as the CIO for a financial services firm, focusing on FedRAMP compliance and security. He has also served in executive and leadership roles in numerous industry verticals. Steffen has presented at numerous industry conferences and has been interviewed by multiple online and print media sources. Steffen holds over a dozen technical certifications, including CISSP and CISA.

Kenneth Buckler, CASP, is a research director of information security/risk and compliance management for Enterprise Management Associates, a leading industry analyst and consulting firm that provides deep insight across the full spectrum of IT and data management technologies. Before EMA, he supported a Federal agency’s Enterprise Visibility program, providing security insights and compliance trending for the agency’s national network of computers and devices. He has also served in technical hands-on roles across multiple agencies in the Federal cyber security space and has published three Cyber Security books. Ken holds multiple technical certifications, including CompTIA’s Advanced Security Practitioner (CASP) certification.

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