Karen Randall is a senior managing director at Guidepost Solutions, bringing extensive experience advising executives on cybersecurity, enterprise risk, and security program design. Ms. Randall has led complex security initiatives across regulated and high-growth environments, serving healthcare, financial services, technology, and other mission-critical sectors. Ms. Randall is known for aligning security strategy with business objectives, including operational resilience, regulatory compliance, and transaction readiness.
Ms. Randall advises clients on cybersecurity, privacy, and AI governance, risk management, and control frameworks. She leads security assessments, maturity evaluations, and roadmap development aligned to established standards, including multiple NIST standards and frameworks, SOC 2, HITRUST, and the HIPAA Security, Privacy, and Breach Notification Rules. She also leads program development and assessments for other state privacy laws (CCPA/CPRA) and other privacy standards such as GDPR. Her work supports boards, executive teams, and investors in addressing cyber risk, strengthening internal controls, and integrating security into broader enterprise and growth strategies. She routinely supports matters involving regulatory preparation, mergers and acquisitions, incident readiness, and enterprise security transformation.
Prior to joining Guidepost, Ms. Randall held senior executive and advisory roles spanning consulting, corporate leadership, and applied research. She built and led enterprise-wide security and governance organizations, serving as chief information security officer and virtual CISO for organizations undergoing rapid growth and acquisition. Her earlier experience also included executive leadership in consulting environments, advising clients on risk management, security architecture, and crisis response, as well as research leadership roles supporting sensitive and high-impact scientific initiatives.
Ms. Randall has deep expertise in standing up first-time security functions, developing scalable programs, and leading cross-functional teams. Her work included achieving rigorous third-party certifications and audits, reducing operational risk and cost through vendor optimization, and mentoring high-performing security and risk professionals. She has also supported investment due diligence by evaluating cybersecurity posture, scalability, and readiness.
Ms. Randall’s expertise across cybersecurity, enterprise risk, and security governance strengthens Guidepost’s ability to deliver trusted advisory services to clients navigating complex regulatory, transactional, and operational risk environments.
DID YOU KNOW?
Karen starts her mornings with a walk and qigong, and she loves exploring the world on horseback.
