Security Program Transformation Podcast

By: Sidekick Security
  • Summary

  • 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.
    © 2024
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Episodes
  • From DMZs to DevSecOps: Building Modern AppSec Programs with Gunnar Peterson
    Jan 15 2025
    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...
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    1 hr and 15 mins
  • From Cost Center to Business Driver: Making Security a Strategic Asset
    Oct 30 2024
    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
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    1 hr and 16 mins
  • Tech Debt, Compliance, and Strategy: A Deep Dive with the CDC’s CISO
    Oct 1 2024

    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

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    1 hr and 3 mins

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