How Many CTOs?

Incident Response and Disaster Recovery

Preparing for outages, running tabletop drills, and building resilience so engineering orgs recover quickly when things go wrong.

Episodes

S2E40 Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between Brad & Scott Brad & Scott discuss TaskRabbit's overnight AWS region migration from us-west-1 to us-west-2, describing the months of preparation, detailed runbook, large war-room call, minor cleanup issues, and why periodic region moves can serve as valuable "hygiene" to relearn and document complex systems while advancing disaster recovery and business continuity. They then explain tabletop exercises as structured incident-response drills designed to uncover gaps in process and documentation, sharing scenario ideas like data deletion, token leaks, cloud outages, ransomware, and internal actors, including an embezzlement case where the perpetrator joined incident response. Incident Response and Disaster Recovery Oct 13, 2026 44:51 S2E38 Simplifying Tech Through Empathy and Understanding with Frank Bravo with Frank Bravo, ProLegal Brad is joined by guest Frank Bravo, a Bay Area technologist who spent 30 years as CTO in local media, helping put a newspaper's full editorial content online in 1994, and now serves as CTO at ProLegal, a legal services startup. Frank describes modernizing an old Act! Incident Response and Disaster Recovery Sep 29, 2026 50:13 S2E2 Setting the Tone: Building Trust Through Security Brad & Scott Brad & Scott discuss the role of CTOs in setting a security-minded culture and provide real-life anecdotes of security breaches and incidents. The conversation covers critical frameworks like CIS, SOC 2, and tools like Vanta, Wiz, Drata, and AWS Security Hub. Incident Response and Disaster Recovery Jan 20, 2026 53:52 S1E18 Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin with Greg Conklin Brad & Scott are joined by special guest Greg Conklin for a candid and insightful conversation on what it takes to build high-performing engineering teams. Drawing from their shared time at the telemedicine startup 98point6, the trio unpacks hard-earned lessons around tech debt, operational excellence, and culture-first leadership . Incident Response and Disaster Recovery Jun 10, 2025 47:51 S1E17 Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams Brad & Scott Brad & Scott explore the art and impact of retrospectives in engineering teams. Drawing on their experiences in both software and high-stakes environments like mountain rescue, they discuss the value of retrospectives for continuous improvement, building trust, and uncovering root causes of both successes and failures. Incident Response and Disaster Recovery Jun 3, 2025 42:11

Articles

How can companies effectively respond to security incidents? How can engineering leaders effectively manage technical debt in a startup environment? How can retrospectives improve decision-making in high-stakes environments? What are the differences between unit tests, integration tests, and end-to-end tests? What role does company culture play in the success of engineering teams? What strategies can CTOs use to communicate complex technical concepts to non-technical stakeholders?