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Chief Information Security Officers (CISOs) are responsible for setting and executing organizations’ information security strategies. This role has only grown in importance as a result of today’s increasingly high-stakes threat landscape. To understand these key decision-makers, we interviewed 16 current and former CISOs to understand how they build a security strategy and the day-to-day obstacles that they face. Throughout, we find that the CISO role is strongly shaped by a business enablement perspective, driven by broad organizational goals beyond solely technical protection. Within that framing, we describe the most salient concerns for CISOs, isolate key decision-making factors they use when prioritizing security investments, and surface practical complexities and pain points that they face in executing their strategy. Our results surface opportunities to help CISOs better navigate the complex task of managing organizational risk, as well as lessons for how security tools can be made more deployable in practice.