How to Land Your First Cybersecurity Job

"Penetration tester" is rarely the first job. It's usually a role you grow into after a few years in something more foundational — most people's actual first cybersecurity job is IT support, a SOC analyst seat, or a GRC/compliance role that later opens a path into offensive security. Planning around that reality gets you hired faster than holding out for the job title you actually want.

This assumes you've already made progress on the ethical hacking roadmap — this is about turning that into a job, not building the skills in the first place.

Entry points that actually exist

SOC Analyst (Tier 1) — monitoring alerts, triaging incidents. Heavy on defensive skills, but it's where a lot of offensive-minded people cut their teeth and it teaches you what defenders actually see, which makes you a better attacker later.
IT support / systems administration — not security-titled, but a background in networking and Windows/Linux administration is a legitimate, common path into a security role a year or two later. Employers trust "this person has kept real systems running" more than a resume with certs and no operational experience at all.
GRC (Governance, Risk, and Compliance) — less hands-on-keyboard, but a real entry point, especially if you can speak to frameworks (NIST, ISO 27001) alongside technical basics.
Junior/associate pentester roles — do exist, but are the most competitive entry point and usually want to see a real portfolio, not just certs.

Build a portfolio, not just a resume

A resume with "Security+, eJPT, completed 40 TryHackMe rooms" and nothing else looks like everyone else's resume. What differentiates a candidate:

Published write-ups — a GitHub or personal site with detailed methodology on boxes/rooms you've completed (not just answers — the reasoning). This site's Labs write-ups are an example of the format worth copying: what you tried, what didn't work, why the eventual approach worked.
A documented home lab — screenshots, a network diagram, notes on what you built and why. Proves you can set things up, not just break them.
Any real-world project, even small — a script you wrote to automate part of a workflow, a tool you built to solve a problem you actually had. Employers respond to evidence of initiative more than another certification.

Certifications that matter for getting past HR filters

Covered in more depth in the general roadmap, but for a first job specifically: Security+ clears the widest number of HR keyword filters relative to the effort it takes, and it's often an explicit requirement for government/DoD-adjacent roles (8570 compliance). Don't over-invest in advanced certs before you have any professional experience — the return diminishes fast without work history to back them up.

Interview prep that actually works

Be ready to walk through a project from your portfolio in detail, not just describe it in a sentence. Interviewers probe depth — if you can't explain a decision you made, it reads as copied rather than understood.
Know the fundamentals cold, especially networking (OSI model, common ports/protocols) and basic Linux — these come up constantly in screening interviews regardless of the specific role.
Prepare a real answer for "why security" that isn't generic. "I like hacking things" is what everyone says; a specific project or moment that actually got you interested is more memorable and more credible.

Where to actually find these roles

Company career pages directly, not just aggregator job boards — a lot of entry-level security postings get buried under senior roles on the big boards
Local security meetups and conferences (BSides events are usually cheap/free and genuinely useful for making real contacts, not just resume padding)
Communities built around the platforms you're already using (TryHackMe/HackTheBox Discords, local DEF CON groups) — a surprising number of first jobs come from someone you met, not a cold application

Common mistakes

Holding out exclusively for "penetration tester" as a first title and turning down SOC/IT/GRC roles that would have gotten you in the door faster
A portfolio full of completed rooms with no explanation of process — the reasoning is what's actually being evaluated, not the flag
Over-certifying instead of building experience — a stack of certs with zero hands-on portfolio work reads as someone who studies well, not someone who's done the work

Next step

If your portfolio is thin, the fastest way to build it is going back through Labs and writing up your own version of the methodology, in your own words, for boxes you've already solved.