Strategic Business Executive | CISO | Board Advisor Location: Florida | https://www.linkedin.com/in/drliles/
EXECUTIVE PROFILE Strategic, risk-based executive leader with extensive experience sitting on Executive Leadership Teams (ELT) and advising at the Cabinet level. Proven track record of aligning technology and security with P&L objectives to protect revenue streams, ensure business continuity, and drive operational efficiency. Expert in leading global, cross-functional teams and translating complex technical risks into pragmatic business decisions for CEOs and Boards.
CORE COMPETENCIES
- Strategic Risk Management: Enterprise Risk Management (ERM), Mergers & Acquisitions (M&A) Support, Board Advisory.
- Business Continuity & Resilience: Crisis Management, Supply Chain Security, Brand Reputation Protection.
- Operational Excellence: Budget Optimization (P&L), Global Team Leadership, Digital Transformation.
- Compliance & Governance: Regulatory Strategy (GDPR, NIST, SOC, HITRUST), Audit Reduction.
PROFESSIONAL EXPERIENCE
BLUE CROSS BLUE SHIELD MASSACHUSETTS | Boston, MA (Remote) Interim Chief Information Security Officer (CISO) | Feb 2024 – Dec 2024
Recruited to lead security strategy for a major health insurer, directly safeguarding a $10B revenue stream.
- Crisis Leadership & Business Continuity: Orchestrated the enterprise response to the Change Healthcare cyber incident, ensuring operational continuity and maintaining stakeholder trust during a high-profile industry crisis. Championed a “Minimum Viable Company” (MVC) resiliency model to guarantee organizational readiness for disaster recovery.
- P&L Optimization & ROI: Maximized a $7M budget (operating 33% below industry standard) to deliver enterprise-grade protection, achieving ~49% ROI through strategic resource allocation.
- Strategic Risk & Compliance: Achieved 100% readiness for HITRUST, SOC, and MARS audits, reducing findings by 90% and solidifying the organization’s compliance posture in a highly regulated market.
- Executive Enablement: Equipped senior leadership with actionable insights on shared responsibility, fostering a culture of informed decision-making at the executive level.
HARLEY-DAVIDSON | Milwaukee, WI (Remote) CISO / Deputy CISO | Feb 2023 – Jan 2024
Entrusted with securing the digital landscape of an iconic global brand, including oversight of two operational banks and complex supply chains.
- Enterprise Risk Management (ERM): Developed a global strategy integrating manufacturing, supply chain, and financial services (banking), directly protecting the brand’s financial institutions and legacy operations.
- Operational Resilience & Risk Reduction: Reduced cyber risk exposure by 85% across core business units by launching a next-gen SOC, significantly improving real-time threat detection.
- Supply Chain & Third-Party Risk: Strengthened third-party vendor frameworks and contract revisions to reduce vulnerabilities across the supply chain and financial service providers.
- IT/OT Business Alignment: Integrated IT and Operational Technology (OT) security to ensure secure connectivity between vehicles, manufacturing systems, and financial operations.
ULTIMATE KRONOS GROUP (UKG) | Weston, FL (Remote) Vice President of Security | July 2021 – Dec 2022 Senior Director of Security | Feb 2018 – July 2021
Executive leader for a 65-person global security organization, managing large technical teams in Paris, Singapore, and the US (SOC, Red Team, Engineering, Physical Security, Identity Access Management) to secure SaaS/PaaS/IaaS environments.
- Global Leadership & Operational Scale: Directed diverse global teams, including European operations, ensuring 100% business continuity for cloud-native services.
- Strategic Business Alignment: Built coalitions across 15 business units, aligning IT security goals with enterprise objectives to secure executive buy-in.
- Operational Efficiency & Automation: Increased efficiency through process automation and threat hunting, reducing critical vulnerabilities by 35% and incident response time by 40%.
- Governance & Growth Support: Designed enterprise-wide governance frameworks, achieving 100% regulatory compliance, supporting the company’s rapid growth and cloud transition.
DEPARTMENT OF HOMELAND SECURITY (I&A) | Washington, DC Special Advisor Cyber Division & Acting Director | Nov 2015 – Feb 2018
- Strategic Influence & Policy: Briefed Cabinet-level leaders, the National Security Council, and Congress on critical threats, directly influencing national policy and risk mitigation strategies.
- Operational Optimization: Directed a team of 35 analysts, optimizing resource allocation to deliver 300% more actionable intelligence for enterprise initiatives.
- Policy Development: Led the creation of the U.S. government’s first non-forensic attribution methodology and shaped national policy on technology imports.
US ARMY CORPS OF ENGINEERS | Washington, DC CISO & Cyber Advisor | Jan 2015 – Oct 2015
- Capital Investment Protection: Directed security for a $700M IT investment and 33,000 global users, ensuring protection of critical infrastructure.
- Governance Transformation: Enhanced governance by 60% through the harmonization of enterprise security architecture and risk assessment enforcement.
EDUCATION & CREDENTIALS
- PhD., Information Security/Digital Forensics| Purdue University
- MS., Computer Science (Software Systems Engineering)| Colorado Technical University
- Certified Information Systems Security Professional (CISSP)
