Founder | President | OneAccordConsulting, LLC
https://www.linkedin.com/in/lesmccollum
“Security Is Now, Not Next.”
Lester N. McCollum II is a distinguished cybersecurity and technology executive whose career reflects a rare convergence of strategic leadership, technical depth, and governance excellence. With more than 15 years of executive leadership experience and over three decades of total professional experience, Lester has built a reputation for transforming complex, high-risk environments into secure, resilient, and innovation-enabled enterprises. His work spans financial services, healthcare, and government sectors, where precision, compliance, and operational excellence are not optional—but essential.
Throughout his career, Lester has consistently delivered one of the most compelling outcomes in cybersecurity leadership: zero material findings across more than 20 regulatory examinations, including oversight from the OCC, Federal Reserve, FINRA, SEC, and HIPAA. This achievement is not simply a reflection of compliance rigor, but rather the result of a deeply embedded operational philosophy that integrates risk management into the fabric of business processes. His ability to move organizations beyond “audit readiness” toward sustainable, proactive security maturity has become a defining hallmark of his leadership.
Most recently, Lester served as Senior Vice President and Deputy Chief Information Security Officer at Synchrony, a $122 billion consumer financial services organization. In this role, he was entrusted with enterprise-wide cybersecurity strategy, regulatory engagement, and board-level risk communication. He represented and contributed to the responsible AI governance framework, establishing risk assessment models, approval gates, and security controls for machine learning, generative AI, and agentic AI systems. This forward-looking work positioned the organization to embrace emerging technologies while maintaining rigorous compliance standards safely.
Lester’s leadership at Synchrony also extended to large-scale transformation initiatives, including advancing cloud security to full CNAPP maturity across AWS, Azure, and Google Cloud. Additionally, led efforts to identify and streamline security tools to eliminate overlapping functions and lower security risks, and he redirected substantial financial resources toward modernization and automation. These initiatives not only boosted operational efficiency but also strengthened the organization’s ability to detect, respond to, and mitigate cyber threats in real time.
Before his role at Synchrony, Lester served as Chief Information Security Officer at the University of Chicago Medicine, where he led the security program for a $2 billion academic health system. There, he restructured the organization’s cybersecurity posture, achieving zero HIPAA findings across multiple audit cycles while significantly improving incident response times and strengthening overall resilience. His ability to align cybersecurity strategy with clinical, research, and operational priorities demonstrated his skill in navigating highly complex and mission-critical environments.
Lester’s tenure at MissionSquare Retirement further solidified his reputation as a transformational leader. Over the course of a decade, including five years reporting directly to the CEO, he guided the organization through a period of 300 percent growth while maintaining flawless regulatory outcomes across SEC and FINRA examinations. He built and scaled enterprise security capabilities from foundational operations to advanced, real-time monitoring environments, ensuring both regulatory compliance and business agility.
A defining aspect of Lester’s career is his commitment to enterprise data protection as a strategic discipline. He has designed and governed data security frameworks aligned with global standards such as GDPR, CCPA, NYDFS, PCI, and HIPAA, ensuring that data protection is not treated as a reactive compliance exercise but as an integrated component of business operations. His leadership in reducing unauthorized data transmission by over 50 percent underscores his ability to deliver measurable, high-impact results.
Beyond governance and strategy, Lester brings hands-on technical fluency that sets him apart from many executive leaders. He developed a Cloud Security Assessment Engine, a Python-based, AI-driven platform that automates multi-cloud security posture evaluations. This innovation reflects his ability to bridge executive oversight with practical engineering, enabling organizations to leverage advanced analytics and machine learning for continuous risk assessment and improvement.
In addition to his corporate leadership, Lester is deeply engaged in the broader technology and governance ecosystem. He serves on multiple advisory boards, including Lumity, Black Kite, Vation Ventures, and IANS Research, where he contributes strategic insights on cybersecurity, innovation, and enterprise risk. He is also an Adjunct Professor of Cybersecurity at North Carolina Central University, where he mentors the next generation of technology leaders and emphasizes the intersection of technical expertise and business acumen.
Lester’s influence extends beyond organizational boundaries into thought leadership and industry impact. He has been recognized as one of the Top 100 CISOs and Deputy CISOs globally and frequently participates in public speaking engagements focused on AI governance, cybersecurity leadership, and enterprise risk. His perspectives on building diverse, high-performing teams and fostering inclusive leadership cultures have also contributed to his standing as a respected voice in the field.
At his core, Lester is driven by a commitment to service, impact, and legacy. His personal philosophy—“I play for the name on the front of the jersey, not the name on the back”—reflects a leadership style rooted in collaboration, accountability, and purpose. As he continues to expand his contributions through board service and advisory roles, he remains focused on helping organizations navigate complexity, manage risk, and unlock sustainable growth.
Character: Lester exemplifies integrity through his unwavering commitment to ethical leadership and accountability in highly regulated environments. He consistently prioritizes organizational success over individual recognition, demonstrating humility and purpose-driven leadership. His dedication to mentoring others and giving back reflects a deep sense of responsibility to both his profession and community.
Knowledge: Lester possesses a rare blend of technical expertise and strategic insight, enabling him to navigate both engineering complexity and executive decision-making. His deep understanding of cybersecurity, AI governance, and regulatory frameworks allows him to anticipate emerging risks and opportunities. He continuously evolves his knowledge base, ensuring he remains at the forefront of technological and industry advancements.
Strategic: Lester approaches challenges with a forward-looking mindset, aligning cybersecurity and technology initiatives with broader business objectives. He has a proven ability to transform organizations through scalable, high-impact strategies that drive measurable results. His leadership consistently balances innovation with risk management, ensuring sustainable and resilient growth.
Communication: Lester is highly effective in translating complex technical concepts into clear, actionable insights for boards and executive stakeholders. He fosters alignment across diverse teams by communicating with clarity, confidence, and purpose. His ability to engage audiences—from technical teams to boardrooms—strengthens organizational cohesion and decision-making.
