Key Responsibilities and Required Skills for Lead Cybersecurity Attack & Penetration Tester

🎯 Role Definition

The Lead Cybersecurity Attack & Penetration Tester drives the offensive security program by designing and executing advanced adversary simulation, red team engagements, and targeted penetration tests across networks, cloud environments, web and mobile applications, and OT/IoT assets. This leader shapes testing methodology, mentors testers, integrates testing outputs with vulnerability management and incident response, and ensures testing activities align with regulatory requirements (PCI DSS, ISO 27001, NIST) and enterprise risk priorities. The role blends hands-on technical expertise with program leadership, stakeholder management, and continuous improvement of tools, processes, and metrics.

📈 Career Progression

Typical Career Path

Entry Point From:

Senior Penetration Tester / Offensive Security Engineer
Red Team Operator / Senior Red Teamer
Security Consultant specializing in application, network, or cloud testing

Advancement To:

Head of Offensive Security / Red Team Lead (global)
Director of Security Testing & Assurance
Chief Information Security Officer (CISO) or VP of Security

Lateral Moves:

Security Architect (secure design & threat modeling)
Incident Response / Threat Hunting Lead
DevSecOps Engineering Lead

Core Responsibilities

Primary Functions

Lead, plan, and execute complex penetration testing and red team engagements across enterprise environments, including external/internal networks, cloud platforms (AWS, Azure, GCP), web and mobile applications, APIs, Active Directory ecosystems, and IoT/OT systems, ensuring tests mirror realistic threat actor tactics, techniques, and procedures (TTPs).
Define and maintain offensive security frameworks, playbooks, and methodologies (e.g., MITRE ATT&CK alignment) to standardize testing, reporting, and remediation verification across the organization.
Design and run multi-week red team campaigns that simulate advanced persistent threats (APTs) and evaluate detection, response, and containment capabilities across SOC, EDR, and SIEM platforms.
Perform comprehensive vulnerability discovery and exploitation planning that includes privilege escalation, lateral movement, persistence, and exfiltration scenarios—then ethically validate findings to measure real business risk without providing unsafe exploit steps in documentation.
Lead threat modeling workshops with engineering, product, and architecture teams to identify high-value assets, attack surfaces, and mitigations early in the development lifecycle.
Oversee authenticated and unauthenticated application security assessments, including manual code review guidance, dynamic analysis, and integration of SAST/DAST findings into actionable remediation plans.
Drive cloud security offensive activities: cloud misconfiguration assessments, identity and access testing, and exploitation validation for IAM, serverless, container orchestration, and infrastructure-as-code.
Coordinate red-blue team exercises and purple team sessions to validate controls, tune detections, and produce prioritized telemetry-based remediation actions for the SOC and platform teams.
Mentor, hire, and develop a high-performing offensive security team; define career paths, run calibration sessions, and own performance management for penetration testers and red-teamers.
Review, approve, and present technical test plans, rules of engagement, and risk acceptance forms to stakeholders and legal/compliance owners prior to every engagement.
Produce detailed, actionable technical reports and executive summaries that map findings to business impact, remediation priority, and residual risk—ensuring clarity for engineering and leadership audiences.
Validate remediation and perform regression testing to confirm that fixes close the vulnerability without introducing regressions or backdoors.
Collaborate with Vulnerability Management and Patch Management teams to integrate penetration test results into the enterprise remediation lifecycle and tracking systems (e.g., ticketing, SLAs).
Provide expert-level advice to product, engineering, and platform teams on secure design patterns, hardening recommendations, and mitigation strategies informed by offensive testing results.
Maintain and operate offensive tooling and automation (e.g., C2 frameworks, custom toolkits, exploit development environments) while ensuring safe, authorized, and auditable use across the team.
Stay current on adversary trends, emerging vulnerabilities, zero-days, and public exploits; translate intelligence into new test cases and detection requirements for the SOC.
Lead purple-team and tabletop incident response exercises that incorporate red team learnings to improve playbooks, detection rules, and containment procedures.
Ensure all offensive testing activities comply with legal, regulatory, and contractual obligations, and coordinate with legal and privacy teams to manage risk and data handling requirements.
Establish and report on KPIs and metrics for the offensive security program—engagement volume, mean time to validate remediation, coverage across assets, and SOC detection effectiveness.
Manage vendor and third-party penetration testing engagements, evaluate vendor findings, and harmonize external testing results with internal program objectives.
Advocate for security by design across DevOps pipelines; partner with DevSecOps to embed testing into CI/CD, IaC scanning, and pre-production release gates.
Provide bespoke targeted training, internal knowledge sharing, and red-team demos to raise organizational security awareness and test-readiness.

Secondary Functions

Build and maintain a repository of reusable test cases, scripts, and proof-of-concept artifacts (with safe handling and access control) to accelerate future engagements.
Support procurement and evaluation of offensive security tools, platforms, and managed red-team services; maintain vendor scorecards and ROI analysis.
Participate in security governance committees, risk reviews, and compliance audits to represent offensive testing perspectives.
Contribute to incident post-mortems by providing offensive test context and potential threat vectors that could have been exploited.
Assist product and engineering teams with ad-hoc security reviews and rapid assessments for high-risk releases or incidents.
Create and deliver targeted training sessions for developers, SREs, and security analysts focused on common exploitation patterns and mitigation tactics.
Maintain documentation for policies, SOPs, and engagement templates; ensure knowledge transfer and runbooks are up to date.
Lead research initiatives to prototype detection rules, telemetry enrichment, and automation that increase SOC efficiency after red team engagements.
Support executive reporting and budget requests for offensive tools, licensing, and staffing needs.
Coordinate with physical security teams when engagements require social engineering, physical access validation, or onsite testing under approved rules of engagement.

Required Skills & Competencies

Hard Skills (Technical)

Offensive security leadership: proven ability to design, manage, and execute enterprise-scale penetration testing and red team programs.
Penetration testing methodologies: deep experience with OWASP, SANS, MITRE ATT&CK mapping, and industry-standard testing frameworks.
Web application security: strong expertise in OWASP Top 10, authentication/authorization flaws, SSRF, XXE, business logic abuse, and API security testing.
Network & infrastructure testing: hands-on skills in assessing firewalls, VPNs, AD/LDAP environments, SMB/RPC, and Windows/Linux privilege escalation and lateral movement techniques.
Cloud offensive security: demonstrable experience testing AWS, Azure, and GCP environments including IAM, serverless, container orchestration (Kubernetes), and IaC weaknesses.
Exploitation & proof-of-concept development: capability to validate vulnerabilities at a safe, controlled level and create PoCs to illustrate impact to engineers (without sharing destructive exploit procedures).
Red team operations and command & control (C2) planning: orchestrating stealthy simulations, persistence techniques, and credential harvesting exercise scenarios.
Scripting and automation: advanced proficiency in Python, PowerShell, Bash, and/or Ruby for custom tooling, automation, and post-exploitation workflows.
Tool proficiency: experienced with common offensive and defensive tools such as Burp Suite, Metasploit, Cobalt Strike alternatives, Nmap, Nessus/Qualys, Ghidra/IDA (for binary analysis), BloodHound, and EDR bypass/rule-testing techniques.
Secure CI/CD & DevSecOps integration: knowledge of embedding security tests in pipelines, IaC scanning tools (Terraform, CloudFormation), and container security scanning.
Reverse engineering & binary analysis: applied knowledge for assessing custom binaries, obfuscated code, or challenging exploitation scenarios.
Threat intelligence and adversary emulation: ability to convert threat intel into realistic test plans and detections for the SOC.
Vulnerability management workflows: experience coordinating findings with ticketing systems, SLAs, and remediation verification processes.
Compliance & regulatory knowledge: familiarity with PCI DSS, ISO 27001, NIST CSF/NIST 800-53, HIPAA, and how offensive testing supports audit objectives.
Reporting & telemetry mapping: ability to create high-fidelity technical reports and executive summaries that map findings to logs, detections, and improvement actions.

Soft Skills

Leadership and mentorship: coach and grow technical talent, create a learning culture, and manage performance for offensive teams.
Stakeholder management: communicate effectively with engineering, product, legal, compliance, and executive audiences; translate technical risk into business impact.
Strategic thinking: align offensive testing objectives with enterprise risk appetite and long-term security roadmap.
Problem-solving: adapt creative approaches to complex environments and constrained rules of engagement.
Clear written and verbal communication: produce concise executive summaries, technical remediation guides, and runbooks.
Collaboration and influence: work cross-functionally to prioritize remediation and integrate security into development lifecycles.
Ethical judgment and discretion: make decisions that balance testing value with legal, privacy, and operational safety.
Time and program management: manage multiple engagements, budgets, and deliverables with strong organizational skills.
Continuous learning mindset: stay current on threat trends, tooling, and emerging technologies.

Education & Experience

Educational Background

Minimum Education:

Bachelor's degree in Computer Science, Cybersecurity, Information Systems, Electrical Engineering, or a closely related technical discipline — or equivalent hands-on experience in offensive security.

Preferred Education:

Master’s degree in Cybersecurity, Computer Science, Information Assurance, or MBA with technical focus for leadership roles.
Advanced coursework or certifications in offensive security, cloud security, or secure software development.

Relevant Fields of Study:

Computer Science
Cybersecurity / Information Assurance
Software Engineering
Network Engineering
Systems Engineering

Experience Requirements

Typical Experience Range:

5–12+ years total cybersecurity experience with at least 3–5 years focused on penetration testing or red team operations; 2+ years in a lead or team management capacity is preferred.

Preferred:

8+ years in offensive security with documented leadership of red team campaigns, program ownership, and cross-functional stakeholder engagements.
Demonstrated track record conducting enterprise-scale assessments across cloud, web, mobile, network, and AD environments.
Experience integrating offensive testing findings into vulnerability management, SIEM/EDR tuning, and security engineering roadmaps.

Relevant certifications (strongly preferred but not always required):

OSCP, OSCE, GPEN, GXPN, GREM, CREST CRT/CCRT, CISSP, or similar industry credentials.