Fast Facts

• Jennifer Ewbank led the CIA’s digital innovation and AI transformation from 2019 to 2024.
• The CIA’s AI overhaul required breaking down deep-rooted culture and technical silos.
• Cybersecurity was embedded at every stage, not bolted on at the end.
• Adversarial thinking and resilience in “boring” fundamentals proved essential for AI security.
• Private sector CISOs face similar risks and must balance speed with security in AI adoption.

The CIA’s Digital Dilemma: Drowning in Data, Racing Against Time

Imagine a fortress brimming with secrets - every conversation, every movement, every digital whisper recorded and waiting to be sifted. That was the CIA in 2019, overwhelmed by a tidal wave of data and racing to harness AI before adversaries could. Jennifer Ewbank, parachuted in from a storied career in espionage, was tasked with steering the Agency’s digital transformation - a mission fraught with organizational inertia, technical debt, and an urgent need to outthink the world’s most sophisticated cyber foes.

Lessons From the Spy World: Culture, Trust, and Relentless Risk

Ewbank’s first revelation: the toughest battles weren’t fought with code, but with culture. Rock star technologists floundered in silos, with rigid budgets and turf wars stifling innovation. To break the gridlock, Ewbank drew on her field experience - aligning teams around shared goals, not just technology.

But culture alone couldn’t secure the Agency’s future. Ewbank redefined cybersecurity’s role, embedding the CISO alongside digital and data leaders at the decision-making table. This was a seismic shift: security became a core ingredient, not an afterthought. In the commercial world, too, the lesson is clear - AI systems deployed without security “guardrails” risk catastrophic exploitation.

To bridge knowledge gaps, Ewbank mandated cross-training - her “digital university” ensured every specialist, from data scientists to network engineers, spoke a common language. In today’s AI-powered enterprises, similar structured education is vital to break down barriers and foster collaboration.

The Boring Basics: Why Fundamentals Still Rule

Despite the high-tech glamour, Ewbank insists that resilience rests on “boring” basics: strong data governance, ethical frameworks, and meticulous identity and access controls. These unglamorous tasks - often neglected in the rush to innovate - form the bedrock of secure AI. Without them, organizations leave the door wide open to manipulation and breach.

Ewbank also championed “adversarial thinking” - the practice of role-playing attackers to anticipate and counter threats. This mindset, long standard in intelligence, is now critical for any business deploying AI. Recent reports from industry watchdogs, such as the National Institute of Standards and Technology (NIST), echo this advice: robust red-teaming and continuous threat modeling are now non-negotiable.

Risky Choices: Imperfection Beats Paralysis

The final, and perhaps most sobering, lesson is about risk ownership. Ewbank made it clear: security can advise, but executives must own and actively manage cyber risk. Inaction, she warns, is often the greatest danger - waiting for perfect solutions only gives adversaries more time to strike. In both government and business, the future belongs to those who act with urgency, eyes wide open to the risks.

WIKICROOK

• CISO (Chief Information Security Officer): A CISO is the executive in charge of a company’s information and data security strategy, overseeing cybersecurity policies and risk management.
• GenAI (Generative AI): GenAI, or Generative AI, is artificial intelligence that creates new content - like text or images - instead of just analyzing existing data.
• Technical Debt: Technical debt is the growing cost and risk from using outdated or quick-fix technology, making future changes harder and more expensive.
• Adversarial Thinking: Adversarial thinking is the practice of anticipating cyber threats by viewing systems from an attacker’s perspective to improve security defenses.
• Identity and Access Controls: Identity and access controls are security measures that verify user identities and restrict access to sensitive data or systems to authorized individuals only.