Lead the planning and execution of offensive security testing across web applications, APIs, infrastructure, and networks. Conduct manual and automated penetration testing and vulnerability assessments; document findings and guide remediation. Work with DevOps, architects, and engineering leads to embed security throughout CI/CD, infrastructure, and data workflows. Plan and run regular security audits and threat modeling sessions; coordinate with third-party firms when needed. Proactively identify and resolve security gaps in complex, custom systems spanning cloud and on-prem environments. Design, implement, and maintain security controls, tooling, and detection capabilities that scale with the business. Develop roadmaps for security certifications (e.g., HIPAA, SOC 2, ISO 27001) and lead technical implementation efforts. Manage incident response procedures, conduct postmortems, and implement long-term prevention measures. Create and maintain high-quality documentation for security processes, infrastructure risks, and compliance status. Stay current on threat landscapes, tools, and best practices relevant to ecommerce, health data, and hybrid infrastructures.