From Navy Sailor to Cybersecurity Chief: What Chris Wheeler Learned About Trust

Key points

• Chris Wheeler, currently Chief Information Security Officer (CISO) at the cyber-insurance firm Resilience, built his security career after serving in the United States Navy.
• Wheeler told SecurityWeek that trust, not technology, is the central challenge of the CISO role.
• His career path reflects a wider pattern of military veterans moving into senior cybersecurity positions in the private sector.
• The CISO role has evolved from purely technical gatekeeper to one that demands boardroom credibility and clear communication with non-technical leaders.

Chris Wheeler did not start out in a corner office. He started on a ship.

After his time in the Navy, Wheeler moved into corporate security and eventually became the CISO, the executive in charge of protecting an organisation's information and systems, at Resilience, a company selling cyber-insurance and security services to businesses.

Speaking to SecurityWeek, Wheeler described the central challenge of the role plainly: the job is trust. Not software. Not threat reports. Trust.

What does a CISO actually do?

A CISO protects the whole organisation from digital attacks, but the role is as much about people as about technology. Wheeler's argument is that a CISO who can't convince a company's board or its everyday staff to take security seriously will fail, however good the technical defences are.

That framing matters. Breaches happen frequently not because a company lacked the right software, but because someone clicked a bad link or shared a password. No tool fixes a culture where staff see security as someone else's problem. We explored that same dynamic in our August story on cybersecurity leaders speaking openly about hacks and burnout, where one episode involved $2 million stolen in a single phone call.

Why does a Navy background help?

Military service builds exactly the habits that hard security work demands: following strict procedures under pressure, communicating clearly in a crisis, understanding that one weak link can sink the whole operation. Wheeler is far from alone. Many senior security executives in the United States came out of military or government intelligence roles, where the consequences of a lapse were measured in something more serious than downtime.

The transition to the private sector isn't frictionless. Corporate culture and shareholder pressure push against the careful, process-first mindset that military training instils. Wheeler's path suggests that friction can be productive rather than fatal.

It's a pattern worth watching. Andreas Gaetje, the CISO we profiled in July, came from economics rather than the armed forces, yet reached a similar conclusion: the leadership wiring matters more than the technical pedigree.

What does this mean for ordinary employees?

For most workers, the CISO is an invisible figure until something goes wrong. If your company's security team feels approachable and explains why rules exist, that's deliberate design, not accident. Staff who understand the reason behind a policy are far more likely to follow it when it counts.

The plain judgement here: Wheeler's framing is correct, and it's undersold. The industry keeps hunting for better tools while the oldest vulnerability, a person who doesn't see why they should care, goes largely unaddressed.

Common questions

What is a CISO and why does the role matter?

A Chief Information Security Officer is the senior executive responsible for keeping a company's data and systems safe from criminals and accidents. As digital attacks grow more costly, boards are paying closer attention to whoever fills that seat.

Can non-technical people become cybersecurity leaders?

Yes, increasingly so. The role requires business judgment and the ability to build trust across an organisation. Technical depth helps, but clear thinking matters just as much.