Podcast Summary: CyberWire Daily – Christian Lees: It's not always textbook. [CTO] [Career Notes]

Host: N2K Networks
Guest: Christian Lees, CTO of RE Security
Episode Date: March 15, 2026

Episode Overview

In this insightful Career Notes episode, CTO Christian Lees (RE Security) shares his unconventional journey into cybersecurity. Moving from early dreams of farming to C-level leadership, Lees recounts how curiosity, serendipity, and resilience shaped his path. This conversation offers practical wisdom for aspiring cybersecurity professionals, emphasizing the importance of adaptability, continuous learning, and embracing opportunities—even when they don’t look exactly as planned.

Key Discussion Points & Insights

1. Early Aspirations and Unconventional Beginnings

• Lees’ childhood dream was to become a farmer, drawn by heavy equipment and unique use cases, offering a refreshing contrast to the typical tech origin story.
  • Quote: “I'm assuming not many people on this show say they want to be a farmer...” (00:55)
• Identifies as a "late bloomer," not attending college immediately, instead working a variety of jobs before realizing higher education was essential to progress.

2. Discovering Technology & The Power of Curiosity

• His entry into computing came through a hand-me-down, outdated 486 DX computer.
  • Initial struggles, like unable to print, led to an important ‘aha’ moment when a friend simply pressed F10 to fix the issue.
  • Quote: “I marveled within like 10 seconds, he's like, oh, dude, you just got to hit F10. And I'm like, really? But it was at that moment where I'm like, oh, this is something good.” (02:12)
• This sparked Lees’ switch to computer science—a turning point leading him to never look back.

3. From Entry Level to Career Growth

• Started professional journey at IBM Global Services in desktop support—a significant leap from student jobs, both in responsibility and pay.
• Fully aware of being at the “bottom,” Lees recognized the importance of hard work and learning on the job.
• Exposure to media outlets during college shaped his interest in information security.
  • Quote: “I just, I knew that I wanted to work towards information security. So I put in my time, I worked and I got exposure to a lot of different things.” (03:35)

4. Defining Moments: Dotcom Bust and Adaptability

• Transitioned from IBM to Level 3 Communications, where working on colocation services and private lines provided hands-on networking experience.
  • Quote: “I would pay them to be here and learn this and have exposure to this enterprise networking gear.” (04:24)
• During the dotcom bust, Lees was shifted into change management—a move he initially resented but later recognized as foundational to effective security.
  • Quote: “By pure luck again, I was introduced to something that is so crucial in security. That's change management, right? Understanding the impact, making sure that it's been burned in.” (05:15)

5. Lessons from Setbacks and Serendipity

• Even when roles didn’t seem ideal, Lees kept his perspective: stay neutral, keep working, and things stabilize.
  • Quote: “When you don't get what you want, it doesn't mean it's over.” (07:35)
• A recurring theme: perceived setbacks (like layoffs or less-preferred assignments) often exposed him to pivotal growth opportunities.

6. Specialization and Security’s Many Facets

• After roles at Level 3 and Trustwave (PCI compliance and pen testing), Lees realized the breadth of information security:
  • “Are you focused on web application security? ...network security? There’s just so many different layers... find what it is that you love and go after it.” (07:19)

7. Leadership and Innovation at InfoArmor

• Ascended to CISO at InfoArmor around the 2010 banking crisis—despite a rocky start, it became “like green fields.”
• Helped diversify offerings, especially in dark web alerts, and practiced what he describes as fearless opportunity-seeking.

8. Advice for Aspiring Security Professionals

• Be relentlessly curious—break things, fix them, don’t fear friction points.
• Accept that you will do “stuff that you don't really want to do”—do it well anyway, and new opportunities follow.
• Main Takeaway Quote: “It's not always textbook... you may join security field not knowing what you’re going to do, but by being that curious person and breaking things and putting it back together, you'll find you're the right way and just never stop being curious.” (08:00)

Notable Quotes & Memorable Moments

• “If I get 50% of what I want, I'm lucky. You don't always get what you want and when you don't get what you want, it doesn't mean it's over.”
  — Christian Lees (07:35)

• “Use every moment you have and every opportunity to the best of your ability. It's not always textbook. Define friction points in it, you may join security field not knowing what you're going to do, but by being that curious person...you'll find you're the right way and just never stop being curious.”
  — Christian Lees (08:00)

• “There's just not enough of us understand that you have to cut your teeth on things and sometimes you get stuff that you don't really want to do...just do it really well and the world will be your oyster.”
  — Christian Lees (08:40)

Segment Timestamps

• 00:55 - Christian Lees shares his early career journey and initial dreams
• 02:12 - Discovery of computing through a donated computer, embracing curiosity
• 03:35 - First job at IBM Global Services and pivot to information security
• 04:24 - Career-defining exposure to network engineering at Level 3 Communications
• 05:15 - Learning the value of organizational change management post-dotcom bust
• 07:19 - On the diversity of roles in cybersecurity and finding one’s passion area
• 08:00 - Career advice for those entering or growing in the security field

Summary

Christian Lees’ story is a testament to the unpredictable and rewarding nature of a cybersecurity career. His journey—from prospective farmer to CTO—underscores the power of hard work, curiosity, and embracing life’s detours. He encourages newcomers to be adaptable, seek learning in every role, and remain curious. Above all, Lees insists that even when your path isn’t “textbook,” perseverance and openness to unexpected opportunities will serve you well.