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Gary Hayslip

Gary Hayslip is a cybersecurity executive known chiefly for his work as a field chief information security officer and for co-writing a widely used series of reference guides for security leaders; he currently serves as Field CISO and Executive in Residence at Zenity [1]. He is a military veteran who later moved into civil service and industry security leadership, and he has described completing an MBA specifically to prepare himself for dealing with senior executives, admirals, and large budgets after retiring from military service [2].

Hayslip is best known for co-authoring the "CISO desk reference guide" book series with Matt Stamper and Bill Bonney, a project he has said began not as a commercial venture but as an outgrowth of articles he was writing to help military veterans understand what it meant to work as a security practitioner or CISO on the civilian side [2]. According to his own account, the idea to turn that material into a book came up informally in conversation with Stamper and Bonney at a startup event, and the three writers decided that presenting a chapter topic through three distinct professional perspectives, with Bonney's more strategic outlook contrasted against his own more practitioner-oriented view, would give readers a fuller picture of the role [2]. He has noted that the books have since been translated into multiple languages and have reached readers internationally, citing an encounter with an MGM executive who said he used the guide while transitioning from military cyber command work into a private-sector CISO position [2].

In discussing his approach to security leadership, Hayslip has emphasized that the work is rarely black and white, arguing that practitioners must learn to manage risk, organizational politics, and competing priorities rather than apply fixed rules, and he credits mentors, including CIOs, other CISOs, and business executives, with correcting his early assumptions [2]. He has also stressed humility in the role, acknowledging that no organization achieves complete security and framing the CISO's job as continual risk management rather than the pursuit of an unattainable perfect state [2].

Beyond his writing, Hayslip has advised security professionals to prioritize peer engagement over isolated decision-making, recommending that practitioners in similar roles actively share information about ongoing projects, recurring challenges, and vendor evaluations as a way of improving collective practice heading into 2025 [3].

Insights & ideas

Gary Hayslip stresses that security leaders should not operate in isolation. He argues that CISOs and practitioners should actively engage with peers doing similar work, sharing information about current projects, challenges, and vendor evaluations rather than trying to solve problems alone, since the whole community is grappling with the same issues [1].

He also emphasizes humility and collaboration as core to security leadership, noting that his CISO desk reference guides were written with co-authors Matt Stamper and Bill Bonney specifically to capture multiple perspectives, since Bonney's strategic view and his own practitioner viewpoint produced richer chapters than a single voice could [2]. The books grew out of his effort to help military veterans transitioning into cybersecurity understand what the CISO role actually entails [2]. He acknowledges that no organization achieves 100% security, reinforcing his broader theme that leadership in this field depends on shared knowledge and realistic expectations rather than individual mastery [2].

Experience

  1. VP, CISO in Residence (Field CISO)
    ZenityJul 2026 to Present
  2. Strategic Advisor
    HalcyonMay 2026 to Present
  3. VP, CISO in Residence (Field CISO)
    HalcyonSep 2025 to May 2026
  4. Co-Founder & Member, Board of Directors
    CISO DRG PublishingApr 2015 to Present
  5. Member of the Board of Advisors
    iVerifyJan 2026 to Present
  6. Member Board of Directors
    San Diego Cyber Center of Excellence (CCOE)Dec 2025 to Present
  7. Management Information Systems (MIS), Member of the Board of Advisors
    San Diego State UniversitySep 2024 to Present
  8. Member of the Board of Advisors
    NisosMar 2023 to Present

Education

Media & appearances

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