How Many CTOs?

Security and Compliance

Security culture, compliance pressure, and building trust with customers through responsible technology practices.

Episodes

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! Security and Compliance Sep 29, 2026 50:13 S2E28 Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers Brad & Scott Brad & Scott discuss token spending and the "token maxing" backlash, sparked by a GitHub Copilot budget issue and broader industry moves to optimize tokens. The hosts argues companies should focus on value and learning rather than premature token optimization, while still adding circuit breakers to prevent runaway costs. Security and Compliance Jul 21, 2026 01:00:30 S2E24 AI and the Data Swamp In Your Backyard with Ben Wilcox with Ben Wilcox, ProArch Brad & Scott interview guest Ben Wilcox, CTO and CISO of ProArch, a Microsoft-focused data and AI system integrator. Wilcox describes his path into system integration, from cloud transformation and building managed security services, and now focused on helping customers adopt AI securely. Security and Compliance Jun 23, 2026 47:33 S2E13 Balancing Innovation and Safety: CTOs Check-In About AI Evolution Brad & Scott In this "What's on your mind? " episode of the "How Many CTOs Does It Take? Security and Compliance Apr 7, 2026 32:06 S2E12 Engaging Employees in Security Appreciation with Robert Siciliano with Robert Siciliano Brad welcomes Boston-raised security speaker Robert Siciliano, who traces his path into security from early experiences with crime, teaching physical self-defense, and being hacked in the mid-1990s. Robert argues that most corporate security training is compliance-driven "security theater" focused on phishing, creating security fatigue while leaving human behavior unchanged. Security and Compliance Mar 31, 2026 57:59 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. Security and Compliance Jan 20, 2026 53:52 S1E40 The Documented SDLC: Why Every Team Needs One (and When) Brad & Scott Brad & Scott start with a quick retrospective, or is it an encore, of recent rock concerts before stage-diving into a lively discussion about the Software Development Life Cycle (SDLC) : what it is, when it matters, and how teams can keep it useful instead of bureaucratic. They explore how the SDLC functions as the connective tissue between engineering, product, and leadership, ensuring teams stay aligned as they grow. Security and Compliance Oct 21, 2025 57:51

Articles

How can companies balance the need for rapid innovation with maintaining data security? How can companies effectively respond to security incidents? How can organizations shift from security awareness to security appreciation among employees? How can system integrators help businesses transition to AI and cloud platforms? What are the key components of a documented Software Development Life Cycle (SDLC)? What are the limitations of traditional security awareness training? What are the security risks associated with AI and supply chain vulnerabilities? What strategies can CTOs use to communicate complex technical concepts to non-technical stakeholders?