Part of the Cybersecurity Career Guide — This article is one deep-dive in our complete career guide series.

Cybersecurity Career Roadmap: Step-by-Step

By HADESS Team | February 28, 2026 | Updated: February 28, 2026 | 10 min read

Table of Contents

• How This Roadmap Works
• Phase 1: Foundation (Months 0-6)
• Phase 2: Entry-Level Role (Months 6-18)
• Phase 3: Specialization (Years 2-4)
• Phase 4: Senior Practitioner (Years 4-7)
• Phase 5: Leadership and Expertise (Years 7+)
• Specialization Roadmaps
• Common Roadmap Mistakes

How This Roadmap Works

This cybersecurity career roadmap 2026 lays out the progression from zero to senior practitioner in concrete phases. Each phase has specific milestones, skills to build, certifications to pursue, and roles to target.

The roadmap is not linear — people enter at different phases depending on their background. An experienced IT professional might skip Phase 1 entirely. A career changer from a non-tech field needs to work through every phase. Use the skills assessment to determine which phase matches your current state.

This roadmap covers the general path. For role-specific roadmaps, see our guides on the SOC analyst path, penetration tester career, and other specializations in the career path explorer.

Phase 1: Foundation (Months 0-6)

Goal: Build the technical fundamentals that every security role requires.

Skills to Build

Networking. TCP/IP model, DNS, DHCP, HTTP/HTTPS, common ports and protocols, subnetting, basic routing. You need to understand how data moves between systems before you can understand how attackers intercept or manipulate it.

Operating systems. Windows and Linux at an administrative level. Active Directory basics, Group Policy, file permissions, service management. Set up a Windows Server and an Ubuntu machine in VirtualBox and manage them through the command line.

Basic scripting. Python for automation and data parsing. Bash for Linux task automation. PowerShell for Windows environments. You do not need to be a developer — you need to write scripts that automate repetitive tasks and parse log data.

Security fundamentals. CIA triad, risk management basics, common threat types (phishing, malware, ransomware, social engineering), authentication and authorization concepts, basic cryptography.

Milestones

• Set up a home lab with VirtualBox (Windows Server, Kali Linux, Ubuntu)
• Complete Security+ study material
• Write 5+ scripts that automate a real task
• Complete at least one CTF or TryHackMe learning path
• Attend one security meetup or conference (BSides, OWASP chapter)

Certification Target

CompTIA Security+ (SY0-701). This is the standard first certification. It covers all foundational domains and is recognized by virtually every employer. Plan your preparation with the certification roadmap.

What to Read

The NIST Cybersecurity Framework provides the big picture of how security programs are structured. Read it early — it gives you context for everything you will learn later.

Phase 2: Entry-Level Role (Months 6-18)

Goal: Land your first security position and build professional experience.

Target Roles

• SOC Analyst Tier 1
• Junior Security Analyst
• IT Security Administrator
• GRC Analyst (Junior)
• Vulnerability Analyst

See our full breakdown of entry-level cybersecurity jobs for details on each role.

Skills to Build On the Job

SIEM operations. Whichever SIEM your organization uses — Splunk, Microsoft Sentinel, QRadar, Elastic — learn it deeply. Write queries, build dashboards, tune detection rules. SIEM proficiency separates effective analysts from mediocre ones. Explore SIEM skills on the platform.

Incident handling. Learn your organization’s incident response procedures. Understand escalation criteria, evidence preservation, and documentation standards.

Vulnerability management. If your role includes vulnerability work, master at least one scanning platform and learn to prioritize findings by actual risk, not just CVSS scores.

Communication. Write clear incident summaries. Present findings to non-technical stakeholders. This skill compounds over your entire career.

Milestones

• Complete 90 days in your first security role
• Handle your first real incident from detection to resolution
• Earn one additional certification (CySA+ for analysts, or a cloud cert for engineering)
• Develop one automation script that your team actually uses
• Start building your professional network actively

Certification Targets

CySA+ (for SOC/analyst track). Validates threat detection and response skills.
AWS Cloud Practitioner + Security Specialty (for cloud track). If your organization uses AWS.
SSCP (for broad security track). ISC2’s practitioner-level certification.

Phase 3: Specialization (Years 2-4)

Goal: Choose a specialization and build deep expertise.

This is where the general roadmap branches. By year 2, you should have enough exposure to know which area of security interests you most. The main branches:

Offensive Security Track

• Intermediate penetration testing skills
• Web application security (OWASP Top 10 in depth)
• Network exploitation and post-exploitation
• Target: Junior Penetration Tester or Red Team Associate
• Certification: OSCP, PNPT, or GPEN
• Related: Penetration tester career guide

Defensive Security Track

• Advanced SIEM and detection engineering
• Threat hunting methodology
• Incident response and digital forensics
• Target: SOC Tier 2/3, Threat Hunter, or IR Analyst
• Certification: GCIH, GCFA, or BTL1

Security Engineering Track

• Infrastructure security architecture
• Cloud security (AWS/Azure/GCP security services)
• Automation and infrastructure as code
• Target: Security Engineer or Cloud Security Engineer
• Certification: AWS Security Specialty, AZ-500, or CCSP
• Related: Cloud security engineer guide

GRC and Management Track

• Risk management frameworks (ISO 27001, NIST RMF)
• Audit and compliance programs
• Security policy development
• Target: Senior GRC Analyst, Risk Manager
• Certification: CISA, CRISC, or CGRC
• Related: GRC analyst career

Use the career path explorer to see detailed progression paths for each specialization.

Milestones

• Complete a specialization certification
• Lead a project or investigation independently
• Present at a team meeting or internal training
• Contribute to a security tool, process improvement, or blog post
• Mentor a more junior team member

Phase 4: Senior Practitioner (Years 4-7)

Goal: Become a subject matter expert and start influencing team strategy.

What Changes at Senior Level

You stop being told what to work on and start deciding what matters. Senior security roles require judgment, strategic thinking, and the ability to translate technical risk into business language.

Technical depth. You are the person others come to with hard questions in your specialization. You design solutions, not just implement them.

Cross-domain knowledge. You understand how your specialization connects to others. A senior penetration tester understands defensive operations. A senior SOC analyst understands attacker methodology.

Leadership without authority. You influence engineering teams to fix vulnerabilities, convince management to fund security initiatives, and guide junior team members — often without direct authority over any of them.

Target Roles

• Senior Security Engineer
• Lead Penetration Tester
• Threat Hunt Lead
• Senior GRC Analyst / Risk Manager
• Security Architect

Certification Targets

CISSP. The standard senior-level certification. Requires 5 years of experience. Validates broad security management knowledge. Study resources in the certification roadmap.

Specialization certs: OSWE (web), OSED (exploit dev), GCTI (threat intel), CCSP (cloud security).

Salary Expectations

Senior practitioners earn $120,000-$180,000+ in the US depending on specialization and location. Use the salary calculator for your specific market.

Phase 5: Leadership and Expertise (Years 7+)

Goal: Shape security strategy at the organizational or industry level.

Two Paths Forward

Management track: Security Manager → Director of Security → VP Security → CISO. This path requires business acumen, people management, board communication, and budget management alongside technical credibility.

Expert track: Principal Security Engineer, Staff Researcher, Distinguished Engineer. This path requires deep technical expertise, industry contributions (talks, papers, tools), and the ability to solve problems nobody else can.

Both paths are valid. Neither is better. Choose based on what energizes you — managing people and strategy, or solving hard technical problems.

Certification Targets

CISM (management track). Information security management.
CCISO (management track). Chief information security officer certification.
Advanced specialization certs (expert track). OSCE3, GXPN, or equivalent.

Consider coaching to navigate career decisions at this level — the choices have long-term implications and outside perspective helps.

Specialization Roadmaps

Each specialization has a detailed roadmap on the platform:

Find your best-fit path with the roadmap selector.

Common Roadmap Mistakes

Skipping the foundation. Jumping into advanced topics without solid networking and OS knowledge. Everything in security builds on IT fundamentals.

Staying in Phase 2 too long. Some people stay in SOC Tier 1 for 3-4 years without specializing. Comfortable but career-limiting. Move to Phase 3 by year 2.

Certification-only approach. Collecting certifications without building real skills. Certifications open doors; skills keep you employed and advancing.

Ignoring soft skills. Technical ability plateaus as a differentiator around year 5-7. After that, communication, leadership, and business understanding determine career trajectory.

Not tracking progress. Without clear milestones, it is easy to feel stuck. Use the HADESS career path explorer to track your progression against defined milestones.

Related Guides in This Series

• How Long Does It Take to Get Into Cybersecurity?
• Cybersecurity Career Switch: From IT to Security
• What is a SOC Analyst? Complete 2026 Guide

Take the Next Step

Build your personalized roadmap. The HADESS roadmap selector recommends a certification and skill path based on your background, target role, and available study time.

Assess your current phase. Take the skills assessment to see exactly where you are in the roadmap and what to focus on next.

Get started free — Create your HADESS account and start progressing through your cybersecurity career roadmap.

Frequently Asked Questions

How long does it take to reach a senior security role?

Typically 4-7 years of focused work. Some people reach senior faster by specializing early and working at organizations with strong security programs. Others take longer if they switch specializations or spend extended time in entry-level roles.

Can I skip entry-level and go straight to a specialized role?

Rarely. Even experienced IT professionals need 1-2 years of direct security experience before most employers will consider them for specialized roles. The exception is if your IT role already included significant security responsibilities.

Is the CISO path realistic?

Yes, but it requires both technical credibility and business skills. Most CISOs have 10-15 years of progressive security experience. The management track from Phase 4 onward is the typical CISO pipeline.

Should I follow this roadmap exactly?

No. This is a general framework. Your specific path will vary based on your background, interests, opportunities, and market conditions. Use it as a reference, not a rigid plan.

How important are certifications versus experience?

Both matter but at different phases. Certifications are more important for entry-level and mid-level transitions (they get you past HR screening). Experience becomes more important at senior levels where hiring managers care more about what you have actually done.

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HADESS Team consists of cybersecurity practitioners, hiring managers, and career strategists who have collectively spent 50+ years in the field.