Inside Illumio CEO Andrew Rubin’s Cybersecurity Leadership Playbook

When our CEO, Andrew Rubin, walked into his first job selling telecom infrastructure decades ago, he admits that he didn’t have a clue what he was doing.

“I think the first thing that actually floods to mind is how completely naive and how little I knew,” he said on a recent episode of the Master Move podcast. “You walk in and you don’t really know anything. But that’s the asset. You’re not constrained.”

That same optimism later fueled his founding of Illumio in 2014, and it’s been a defining trait of his leadership ever since.

In his conversation with the Master Move podcast host Craig Gould, Andrew shared candid lessons from building Illumio, revealing what it really takes to lead through uncertainty, scale culture without losing your edge, and make bold decisions in an industry where ambiguity is the norm.

Here’s what every cybersecurity leader can take away from Andrew’s playbook.

Building a company without a map

When Andrew started Illumio, he wasn’t trying to create a new category. He thought segmentation was simply the next evolution of the firewall.

But the market didn’t see it that way.

“There were no analysts writing about segmentation,” he said. “No sales reps with experience selling it. No procurement playbooks for buying it. We had no idea we were stepping into a category creation exercise.”

That lack of clarity could have sunk the company. Instead, Andrew doubled down on conviction.

What Andrew believed kept Illumio going was that he and its early leaders believed the problem they set out to solve was real. “The strategy changed, the go-to-market changed, the timelines were all wrong — but the problem never changed,” he said. “We stayed anchored to that.”

This is a crucial lesson for cybersecurity and business leaders alike: you don’t need perfect visibility to lead. You need conviction, adaptability, and a willingness to keep building through ambiguity.  

As Andrew always says about cybersecurity, “Perfection is the enemy of good.” Leaders have to be ready to iterate and evolve with the business rather than try to work toward one perfect plan.

Why you can’t wait for the tipping point

If you’re looking for a single moment when Illumio “made it,” Andrew had bad news.

“There’s no big tipping point,” he said. “There are thousands of tiny ones.”

A big customer win might help land the next two but not the third. Analyst recognition helps, but it’s not a silver bullet. Every milestone is followed by the next unknown.

But momentum builds, Andrew said. Especially when customers, analysts, regulators, and channel partners all begin to converge on a shared understanding of the problem and the solution.

Andrew likens Illumio’s trajectory to walking a tightrope across a canyon: “We were just early enough to be right. But the only thing separating ‘very early’ from ‘too early’ is bankruptcy. And the only way to avoid that is funding and revenue.”

Innovation doesn’t scale on autopilot

Innovation might come naturally to a startup, but it’s much harder to maintain when you’re a global company with thousands of employees.

And in cybersecurity, standing still is not an option.

“You’re being graded every day on your ability to innovate,” Andrew said. “If you don’t, the market moves on — fast.”

For Illumio, that meant expanding beyond its early on-premises microsegmentation offering to support broader use cases across endpoint and hybrid multi-cloud environments.  

It also meant releasing a second product ten years into the company’s journey. It was born not from a long-term roadmap but from listening closely to customers and remaining open to what they really needed.

Innovation, Andrew argued, isn’t a department. It’s a cultural requirement, one that must be actively led, modeled, and defended from the top down.

Leadership is ownership

Asked what separates good leaders from great ones, Andrew doesn’t talk about charisma or technical expertise. He talks about ownership.

Leadership means signing up for the hard stuff, he said. “The more senior you are, the more you have to insource the hard decisions. That’s the job.”

That also means being relentlessly authentic. Andrew doesn’t try to be someone he’s not, and he doesn’t expect his leaders to either.

“Own who you are. That’s what gets you to the next level,” he said.

For those looking to climb into the C-suite, Andrew offers three pieces of advice:

1. Be authentic. People can spot inauthenticity instantly. ‍
2. Own your decisions. Leadership isn’t about delegating the hard calls but about making them. ‍
3. Lead by example. Your team is always watching. Set the tone with your behavior, not just your words.

Invest in relationships before you need them

Another theme that runs through Andrew’s story: mentorship.

He sees mentors as a kind of cheat sheet for career and business success. For Andrew, mentors are people who’ve lived through the hard stuff and can help him navigate it faster and with fewer mistakes.

But mentorship isn’t passive.

“Advisors don’t come to you,” he said. “You have to invest in the relationship. You have to ask the questions, and you have to show up.”

Sometimes, those relationships become more than just professional assets. “Some of the people who mentored me early on are now some of my closest friends,” he said.

The takeaway: lead despite uncertainty

Andrew’s leadership principles aren’t just reflections on Illumio’s journey — they’re a roadmap for leading in an era defined by uncertainty.  

Cybersecurity, like every modern industry, is evolving faster than ever. AI is rewriting the rules of defense, cloud transformation is reshaping infrastructure, and the line between business risk and cyber risk has all but disappeared. In this kind of environment, waiting for certainty means falling behind.

Andrew’s insights remind us that success today depends on how well you can adapt, decide, and lead through ambiguity.  

The leaders who will shape the next decade of cybersecurity aren’t going to be those who have all the answers but those who have the courage to keep building even when the map isn’t finished yet.

Listen to Andrew’s full interview on the Master Move podcast , and learn more about Illumio.