Chasing Entropy Podcast 019: Balancing Security, IT, and Human Outcomes with Jacob DePriest

In this episode of Chasing Entropy, host Dave Lewis, Global Advisory CISO at 1Password, sits down with Jacob DePriest, the newly appointed CISO and CIO at 1Password. Together, they explore the intersection of security, IT, and the human factors that shape how we defend and sometimes undermine our digital world.From NSA to GitHub to 1PasswordJacob traces his path from early engineering work at the NSA to leading security operations at GitHub, and now into his dual role at 1Password. With roots in engineering and open source advocacy, he shares how those experiences shaped his approach to building secure yet productive environments.Security and Development: A Necessary PartnershipA recurring theme is the relationship between security teams and developers. Jacob emphasizes that security cannot scale without deep integration into the engineering lifecycle. Rather than bolting on controls, he advocates for shared scoreboards, embedded guardrails, and empowering developers to focus on outcomes without unnecessary friction.Secrets, AI, and the Future of RiskThe conversation dives into secrets management and the rise of AI in security. Jacob highlights how smarter alerting and AI-assisted scanning can help reduce noise around exposed credentials. They also discuss the promises and pitfalls of agentic AI, where transparency, governance, and credential security will become defining challenges for enterprises.Balancing Productivity and ProtectionAs both CISO and CIO, Jacob is uniquely positioned to tackle the long-standing tension between IT enablement and security. He argues that these shouldn’t be opposing forces, the shared goal is enabling the business safely and responsibly. Hybrid teams and flexible models, such as customizable unlock experiences in 1Password, illustrate how to strike that balance.Diversity, Culture, and Psychological SafetyThe episode also touches on team culture: hiring for diversity of thought, encouraging dissenting voices, and building psychological safety. Jacob and Dave reflect on how recognition systems, open communication, and intentional leadership can foster stronger, more resilient security teams.Parting Advice for Security LeadersJacob closes with two guiding principles:Focus on outcomes and the big picture, don’t lose sight of the real problems in pursuit of perfect solutions.Appreciate the community of security professionals who face daily challenges in an increasingly complex landscape.Listen now to hear Jacob’s insights on navigating the evolving role of security leaders, the integration of IT and cybersecurity, and how to prepare for the next wave of challenges.As always, be sure to like and subcribe!