CDW Summit 2026: Imagination Is the Secret Ingredient to Solving Some of Tech’s Biggest Challenges

Why Imagination Is Essential to Fixing Cybersecurity

Here’s a funny thing you might not expect the CEO of a cybersecurity company to say: IT doesn’t have a cybersecurity problem, it has a software quality problem.

From Easterly’s point of view, the current approach to cybersecurity relies on aftermarket companies, such as RSA, building cybersecurity bolt-ons and add-ons after software has already shipped and been implemented with organizations of all kinds.

But that goes against the best practices of cybersecurity principles, which call for security to be imagined and integrated at the inception of the software development.

“For nearly four decades, because of misaligned economic incentives, lack of any meaningful technology regulation or software liability regime, technology manufacturers have been allowed to — have actually made the rational business economic decision to — develop and deliver what is flawed, defective, insecure software,” said Easterly.

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But given the eyebrow-singing headlines we’ve seen of rogue agents hacking into systems and structures without the knowledge of their creators, this aftermarket approach to cybersecurity is insufficient for the moment.

“This vulnerability acceleration moment changes a lot of how we’ve been thinking about the cybersecurity business, because if attackers can find and weaponize these flaws and defects faster than defenders can find them, confirm them, validate them, remediate them or place compensating controls around them, well, that means the balance of power may shift,” said Easterly.

Rather than fight to preserve the cybersecurity business model and philosophy that has built the industry, Easterly is actively leveraging that imagination she honed as a child with her Rubik’s cube to imagine new solutions and approaches for this brave new cybersecurity landscape. And she’s encouraging other IT leaders to similarly use their imaginations to solve these emerging problems.

“We have to figure out how to harness the power of imagination of these scenarios without suffering a failure of imagination, because we know our adversaries out there, our adversaries are doing it,” she said. “Our adversaries right now are trying to figure out how they can use AI to turbocharge their attacks, to hold our critical infrastructure, our way of life, at risk. And that is not theoretical.”

With Great Opportunity Comes Great Risk

The arrival of AI to the masses has unleashed a torrent of optimism and pessimism among IT professionals and society at large. Everyone has started to see who in their life is more of an AI skeptic or an AI enthusiast.

But Easterly is in the middle of that continuum, as she acknowledges that AI does potentially afford us with incredible new capabilities, but also exposes us to serious, urgent risks.

“The French philosopher Paul Virilio has this terrific quote, he said, ‘When you invent the ship, you also invent the shipwreck. When you invent the plane, you also invent the plane crash. When you invent electricity, you also invent electrocution.’ Every technology brings with it negativity that’s invented at the exact same time as technical progress,” said Easterly.

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“So, the AI that can protect can also attack. The AI that can prevent fraud can also commit it. The AI that can be used to identify vulnerabilities in code at unprecedented speed and scale can also be used to weaponize them,” she added. “And, as you all know, we are already seeing AI used by threat actors to create exquisite, highly tailored, highly personalized, very difficult-to-detect phishing emails.”

While Easterly keeps a sober, and serious mind about AI’s risk potential, she also sees the need for a response to these risks as a calling and a responsibility that technology leaders must embrace, not shy away from.

“Over the past few years, AI has rightfully, justifiably captured the world’s imagination, but I believe it’s the responsibility of all of us as leaders, as technologists, as operators, as security professionals to be able to harness the power of that imagination without suffering a failure of imagination. We have to be able to build and operationalize this technology but ensure that it is built with security as the top priority,” she said.

Jen Easterly displays a Rubik’s Cube as part of her talk during CDW’s 2026 Summit.

The Real-World Consequences of Failed Imagination

While Easterly is currently CEO of RSA, a renowned cybersecurity company that made its name in the late ’80s through the ’90s, her career has been incredibly varied and afforded her a diverse range of experiences that have shaped the cybersecurity leader that she is today.

While speaking at the CDW Summit, Easterly shared snippets of her stints as director of the Cybersecurity and Infrastructure Security Agency, , commander of the Army’s first cyber operations unit, and firm resilience and cybersecurity operations lead at Morgan Stanley.

She recalled her experience joining then National Security Advisor Condoleezza Rice as she testified to the 9/11 Commission on what happened to leave the U.S. vulnerable to the terrorist attacks that happened that day.

“The last thing that I did before I left the White House and went to my next duty assignment at Fort Meade was to go with her to the Capitol as she testified before the 9/11 Commission. That's me sitting behind her,” said Easterly.

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“And I remember so clearly the words of the chairman of that Commission — it was a guy called Tom Kean. He said, ‘On that September day, we were unprepared. We did not grasp the magnitude of a threat that had been growing for some considerable period of time. It was a failure of management, a failure of policing, a failure of capability, but above all, a failure of imagination,’” she said.

That idea of vulnerability being the manifestation of a failure of imagination stuck with Easterly in a way that she hasn’t let go of since. That is why she felt compelled to impart that wisdom to attendees at the CDW Summit.

“In technology, in cybersecurity, in resilience, in data security, that’s probably the greatest danger: the failure to imagine what’s possible; the failure to imagine how an adversary can weaponize a piece of technology for disruption or destruction; the failure to imagine how a piece of technology might fail and lead to systemic, consequential risks; the failure to imagine, just as importantly, what’s possible, the best of what’s possible,” said Easterly.

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