Security Program Transformation Podcast

Sidekick Security
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Building a cybersecurity program is complicated. Building one that is equipped to truly enable the organization it serves is another thing altogether. Robert Wood from Sidekick Security interviews security leaders from a diverse set of organizations to talk about program transformations. From team design, technology, compliance versus security, and strategic leadership, learn about how to lead a program transformation of your own from people who have gone through it before.

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  1. 2025. 02. 19.

    Drowning in Data, Starving for Insight: Cyber Risk Quantification in Action

    In this conversation, Robert Wood and Mads Bundgaard Nielsen delve into the complexities of cyber risk quantification, exploring Mads' journey into this niche field, the importance of a business-first approach to risk management, and the distinctions between compliance and effective risk management. They discuss foundational steps for initiating risk quantification, the significance of stakeholder engagement, and the challenges of measuring non-financial impacts. The conversation also touches on the limitations of existing risk assessment tools and scoring systems, emphasizing the need for a more nuanced understanding of risk in cybersecurity. In this conversation, Robert Wood and Mads Bundgaard Nielsen delve into the complexities of vulnerability management and risk quantification in cybersecurity. They discuss the challenges organizations face in prioritizing vulnerabilities, the inefficiencies in third-party risk management, and the future of cyber risk quantification. Mads emphasizes the importance of understanding organizational attributes for effective risk management and shares valuable resources for those looking to enhance their knowledge in this field.   Takeaways Cyber risk quantification is often misunderstood and challenging to implement. A business-first approach is crucial for effective risk management. Compliance and risk management serve different purposes and should not be conflated. Defining clear outcomes is essential before starting any quantification project. Simplifying measurement processes can lead to better insights. Stakeholder engagement is vital for successful risk decision-making. Non-financial impacts can be just as important as financial metrics. Quantification should not be an all-consuming task; focus on key scenarios. Understanding the problem space is more important than technical expertise in quantification. Existing risk tools often provide inadequate assessments, necessitating a more tailored approach. It's not true risk quantification, but some level of more specific measurement to vulnerabilities. Our ambition of mitigating vulnerabilities is much larger than our capacity. We need to categorize vulnerabilities based on their actual business risk. The industry drowns in findings from vulnerability tools. Third...

    1시간 21분

  2. 2025. 01. 15.

    From DMZs to DevSecOps: Building Modern AppSec Programs with Gunnar Peterson

    In this conversation, Robert Wood and Gunnar Peterson delve into the complexities of application security (AppSec), discussing its evolution, the importance of building effective AppSec programs, and the need for engaging developers in security practices. They explore the blurred lines between cloud security and application security, the role of posture management tools, and the significance of an asset-centric approach to security. Gunnar emphasizes the importance of understanding key use cases and platforms within an organization, as well as the need for security professionals to broaden their skill sets to navigate the changing landscape of cybersecurity effectively.   Takeaways Application security is evolving, requiring a focus on both technology and human factors. Understanding the organization's current state is crucial for building an effective AppSec program. Coverage and efficacy are key metrics for assessing AppSec initiatives. Engaging developers is essential for successful security practices. In larger organizations, security efforts can become check-the-box activities. The lines between cloud security and application security are increasingly blurred. Posture management tools are emerging to address skill gaps in AppSec. An asset-centric approach to security is gaining traction in the industry. New security professionals should prioritize understanding key business use cases. The future of security will require blending traditional practices with new technologies. Sound Bites "Good judgment comes from experience." "You have to have the humility to recognize." Chapters 00:00  Introduction to Application Security and Its Evolution 02:59. Building an Effect...

    1시간 15분

  3. 2024. 10. 30.

    From Cost Center to Business Driver: Making Security a Strategic Asset

    In this conversation, Robert Wood, CEO of Sidekick Security, interviews Tyler Healy, CISO of DigitalOcean, discussing the evolution of security leadership, the importance of security as an enabler for business growth, and the dynamics of building a security team. They explore the challenges of engaging with customers, fostering internal relationships, and the balance between security and usability. Tyler shares insights on incident management, materiality assessments, and the significance of understanding how a business makes money to effectively align security initiatives with organizational goals. Takeaways Security teams must engage with customers regularly. Understanding business incentives is crucial for security leaders. Security should be seen as an enabler, not a cost center. Building relationships across departments enhances security effectiveness. Product security should empower developers with the right tools. Usability is key to successful security implementations. Incident management processes must include materiality assessments. Availability impacts must be considered in security discussions. Third-party risks need to be managed proactively. Security leaders should balance technical skills with effective communication. Chapters 00:00  Introduction to Security Leadership 06:02  Navigating Security as an Enabler 09:56  Building a Security Team from the Ground Up 15:54  Engaging with Customers and Stakeholders 20:00  Fostering Internal Relationships for Security

    1시간 16분

  4. 2024. 10. 01.

    Tech Debt, Compliance, and Strategy: A Deep Dive with the CDC’s CISO

    Summary In this conversation, Robert Wood and Joe Lewis discuss the complexities of leading cybersecurity efforts within a large organization like the CDC. They explore the balance between security and mission enablement, the nuances of risk management, and the importance of compliance. Joe emphasizes the need for humility in leadership, the value of building a strong team, and the significance of understanding organizational dynamics. The discussion also touches on the challenges of innovation in crisis situations, the importance of effective communication, and the need for continuous personal and professional development in the cybersecurity field. Takeaways Humility is essential for effective leadership in cybersecurity. Balancing security with mission enablement is crucial. Understanding risk transfer dynamics is important for CISOs. Compliance should be viewed as a foundation for security, not a hindrance. Using compliance strategically can enhance decision-making processes. Innovation often requires accepting certain risks during crises. Post-crisis assessments are vital for understanding risks taken. The language of risk must be tailored for different audiences. Non-technical skills are critical for success in cybersecurity roles. Intentional organizational design can break down silos and improve collaboration. Sound Bites "I think the one piece of advice I would have given myself is humility." "We are evolving into a managed cybersecurity service provider." "Not everybody should grow up to be a CISO." Chapters 00:00 Introduction to Cybersecurity Leadership 02:36 Balancing Security and Mission Enablement 07:38 Understanding Risk Transfer in Cybersecurity 12:57 Navigating Compliance and Security 16:29 Using Compliance as a Strategic Tool 21:36 Innovation and Risk Management in Crisis 25:59 Post-Crisis Reflection and Risk Assessment 28:29 The Language of Risk in Cybersecurity 34:42 Developing Non-Technical Skills in Cybersecurity 39:43 Intentional Organizational Design 45:14 Managing Change and Reducing Process Waste 51:12 Identifying and Nurturing Future Leaders 56:29 The Importance of Humility in Leadership

    1시간 3분
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Building a cybersecurity program is complicated. Building one that is equipped to truly enable the organization it serves is another thing altogether. Robert Wood from Sidekick Security interviews security leaders from a diverse set of organizations to talk about program transformations. From team design, technology, compliance versus security, and strategic leadership, learn about how to lead a program transformation of your own from people who have gone through it before.

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