Cybersecurity Advisor

• Conducting penetration testing, assessing and exploiting security flaws, reporting findings, collaborating on remediation, and engaging with policyholders to reduce risk.
• Provide clear and detailed reports, including technical documentation and executive-level summaries.
• Collaborate with development, infrastructure, and security teams to recommend remediation strategies.
• Positively impact Cowbell s bottom line by working with Policyholders and partners to lower Policyholders risk exposure.
• Actively support programs and assigned regions (e.g., Australia).
• Provide technical support to Underwriting by delivering risk insights during policy assessments.
• Engage directly with Policyholders through:
• Risk Assessment calls
• Subjectivity calls
• Claims calls
• Micro-Pen Testing (MPT) execution and deliveries
• Webinars and educational sessions
• Risk report creation, delivery, and introductions
• Platform introductions and walkthroughs, as needed
• Responding to general security inquiries
• Document and maintain historical calls and questionnaires within the Cowbell Platform.
• Support Cowbell s Resiliency Services by delivering advisory and security services that enhance Policyholder resilience.

Stakeholder Engagement

• Act as the primary liaison with Policyholders, Underwriting, and Claims teams to ensure security assessments align with business needs.
• Translate complex technical findings into actionable risk insights that support underwriting decisions and resiliency outcomes.
• Communicate status, key risks, and remediation dependencies clearly to Policyholders and cross-functional teams.
• Cooperate with internal Product, Security, and Resiliency Services teams to ensure Cowbell s platform and reports deliver measurable value to stakeholders.

• Cooperate with cross-functional teams including Underwriting, Claims, Engineering, and Resiliency Services
• Foster a culture of knowledge-sharing, accountability, and continuous learning within the security assessment team.
• Coordinate the execution and delivery of Multi-Point Testing (MPTs), risk assessments, and policyholder-facing reports to ensure timely and accurate delivery.

• Champion penetration testing and security assessment best practices to ensure consistency, accuracy, and measurable risk reduction for Policyholders.
• Leverage data-driven insights to optimize assessment processes and improve overall delivery quality.

• Bachelor s or Master s degree in Computer Science, Cybersecurity, Information Technology, or a related field.
• 4+ years of experience in penetration testing, ethical hacking, or offensive security.