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 Leadership06:02  Navigating Security as an Enabler09:56  Building a Security Team from the Ground Up15:54  Engaging with Customers and Stakeholders20:00  Fostering Internal Relationships for Security