Breaking In: Cybersecurity Careers, Certs, and Real-World Skills

The cybersecurity hiring ecosystem is confusing, inconsistent, and often hostile to capable people trying to break in. Entry-level roles demand experience, certifications are required before the job that provides that experience, and resumes disappear into automated systems before a human ever sees them.
This meetup is a structured roundtable discussion led by Grey Fox, built around real observations from industry conversations and firsthand experience. Rather than prescribing a single “correct” path, the session is designed to surface nuance, tradeoffs, and decision frameworks that participants can apply to their own situations.
Topics introduced for discussion will include:

• Certifications: when to study, when to sit for exams, and when they are truly required
• Practical experience: home labs, Active Directory, DNS, endpoint hardening, attack and defense simulations
• Training platforms vs real-world application: transitioning from guided learning into CTFs and bug bounties
• Visibility and networking: conferences, volunteering, public work, and why referrals matter
• Communication skills and cultural fit: trust, collaboration, and representing technical work to non-technical stakeholders

The emphasis is on discussion, not instruction. Grey Fox’s points are intentionally presented as starting positions to be questioned, refined, and expanded by the group.
Whether you are:

• Pivoting into cybersecurity from IT or another technical field
• Unsure which security role aligns with your interests
• Frustrated with credential requirements and hiring filters
• Or simply looking for clearer mental models about the industry

This session aims to provide clarity, shared insight, and actionable perspective.
Non-members are welcome. Observing is fine. Participation is encouraged.

## FAQs

### Who is this event for?

Anyone interested in cybersecurity careers, especially those trying to break in, pivot roles, or understand hiring realities.

### Do I need prior cybersecurity experience?

No. Some familiarity helps, but the discussion is accessible to those still exploring the field.

### Is this a lecture or a class?

No. This is a discussion-based roundtable. Ideas are introduced to spark conversation, not to deliver fixed answers.

### Can non-members attend?

Yes. Non-members are welcome to participate.