Cybersecurity Leadership: Does Your Organization Measure Up?
5 key traits to look for when recruiting for cybersecurity leadership
It’s a scene familiar to too many organizational leaders: It’s Sunday evening. You’re
settling in with the family after dinner, prepared for an evening of relaxation before the
grind of another week begins. Suddenly your smartphone pings with a calendar
invitation. Subject line: Vendor Security Breach Briefing. Scheduled for 8 a.m. Monday.
The breach? It’s been traced back to a third-party vendor your organization works with.
Your stomach drops.
No details. No context. Just the unsettling implication that something has gone terribly
wrong. What’s been compromised? Who’s affected? How bad is it? Sleep won’t come
easy tonight.
No details. No context. Just the unsettling implication that something has gone terribly
wrong. What’s been compromised? Who’s affected? How bad is it? Sleep won’t come
easy tonight.
It’s become a daily headline, another company, another breach. From global enterprises
to small startups, no one is immune. What’s most alarming is that many of these
organizations already had comprehensive security plans in place. They invested in
tools, trained their teams, and followed compliance protocols. And yet, still, they were
breached.
Cybersecurity isn’t just a technical function or a compliance checkbox; it’s a cultural
imperative. And culture starts at the top.
Carmi Levy is a Canadian technology analyst and journalist and often speaks about the
importance of leadership-driven security awareness. “Too many organizations still treat
cybersecurity as the domain of IT, disconnected from leadership strategy,” he says. “But
in today’s threat landscape, that mindset is dangerously outdated and won’t on its own
keep the bad guys out. Building a resilient security culture requires a leader who doesn’t
just understand the tech, but who can embed security into the very DNA of the
organization.”
“Leadership-driven security awareness is no longer a ‘nice to have’. It’s a business-
critical skill set,” he adds. “The ability to protect brand trust, customer data, and
operational continuity hinges on whether your leaders can champion security as a
shared responsibility.”
Levy suggests organizations look for the following key traits when evaluating leadership
candidates to ensure everyone around the c-suite table aligns with a cybersecurity-first
culture.
1 – Communication and Connection
Strong cybersecurity leaders don’t just communicate, they know how to connect. They
know how to speak to executives and staff in ways that resonate. But it’s not just about
talking; it’s about earning trust, influencing decisions, and navigating the politics of
change in a fast-moving environment.
2 – Business Knowledge
Great cybersecurity leaders go beyond technical expertise; they understand the
business and its strategic goals. Their true value lies in translating complex technical
issues into language that business stakeholders understand and can relate to.
Too often, technical practitioners equate technical problems directly to risk, leaving
decision-makers confused. Leaders play a critical role in bridging that gap by adjusting
both the language and the message to ensure clarity and relevance. A strong technical
understanding enables cybersecurity leaders to challenge assumptions, validate
solutions, and maintain credibility with their teams.
It's not about being the most technical person in the room, however. It's about knowing
enough to ask the right questions and recognize when something doesn’t add up.
3 – Organizational Agility
Cybersecurity leaders don’t just view IT as a service; they see it as a strategic partner.
Their strength lies in understanding how systems fit together and having the strategies
and playbooks ready to respond when incidents occur.
It’s not about knowing how to build every system; it’s about being prepared to lead
through disruption. They also bring the leadership presence needed to rally cross-
functional teams and drive coordinated action.
While everyone plays a role in managing risk, accountability must be clearly defined: the
business owns the risk, and the broader organization is responsible for supporting its
management.
4 – Cybersecurity Competency
Yes, leaders need business savvy, but they also need to walk the walk technically. It’s
not enough to be fluent in compliance. True resilience comes from a layered approach
to protection, supported by proper controls and checks and balances.
Security is not the same as compliance; it requires a deeper understanding of how
systems operate and how risks manifest in real-world environments.
Effective leaders don’t need to build the systems themselves, but they must understand
how those systems fit together and how to assess their integrity. This technical foundation enables them to challenge assumptions, validate strategies, and lead with
confidence in both routine operations and crisis scenarios.
5 – Strategic Vision
Vision is great, but execution is everything. Strong leaders can set priorities and position
cybersecurity as an enabler of business success. But they also know how to navigate
real-world business challenges like budgets and reporting lines.
Because without execution, even the best vision falls flat.
It’s about what you know. And at Phelps, it’s about who WE know. Connect with us
today to discover how we can help secure top-tier cybersecurity leadership helping your
organization be future ready.
The Phelps team is composed of seasoned consultants, researchers, marketers, and leadership advisors who combine deep sector knowledge with a rigorous, value-driven approach to executive search. The firm is committed to aligning vision, values, and agility to spark transformative impact, ensuring that every leadership placement is not only a strategic fit but a catalyst for organizational excellence.
Whether guiding succession planning, conducting board-level searches, or advising on leadership development, Phelps continues to set the standard for executive search across Canada.