Penetration Tester (Team Lead)

Job description

​Penetration Tester (Team Lead) - Min 8 years

Available junior penetration tester roles for candidates with lesser experience

We are looking for a Lead to guide and oversee advanced penetration testing and red team operations, where you’ll leverage your expertise in offensive security to deliver high-value results for clients. You will be the driving force behind multiple engagements, providing both technical leadership and strategic direction to your team while ensuring that all projects are executed efficiently and effectively.

This role requires a unique blend of deep technical knowledge, team management, and consulting experience. You will be responsible for mentoring a skilled team of professionals, ensuring they have the guidance and resources they need to deliver exceptional work while staying ahead of the latest attack methodologies. You will also work closely with clients, translating complex technical findings into actionable recommendations and maintaining strong, ongoing relationships.

Key Responsibilities:

• Project Leadership & Management: Oversee and coordinate the execution of multiple penetration testing and red team engagements from start to finish. Manage project timelines, workloads, and deliverables.

• Team Coordination & Development: Lead a team of testers, assign tasks, and provide guidance and mentorship to help them succeed. Foster both technical skill growth and career development within the team.

• Technical Oversight & Review: Ensure all engagements follow best practices and are aligned with internal standards. Review test plans, evaluate progress, and monitor the technical execution of each project.

• Client Engagement & Communication: Act as the primary point of contact for clients throughout engagements. Present findings in clear, actionable terms to both technical and executive-level stakeholders.

• Sales & Pre-Sales Support: Collaborate with sales teams to support business development efforts by helping craft proposals, answering RFPs, and delivering presales presentations.

• Continuous Improvement & Methodology: Contribute to the improvement and refinement of the company’s testing methodologies, tools, and internal documentation.

• Industry Leadership: Represent the company by participating in public speaking, writing technical blogs, conducting workshops, or presenting at industry conferences to enhance the company’s thought leadership.

Required Qualifications & Experience:

• Min 8 years of offensive security experience: Proven experience leading complex penetration testing or red team projects, managing both the technical and operational aspects of these engagements.

• Strong Technical Skills: Proficient in system administration for both Linux and Windows environments, with a solid understanding of Active Directory. Skilled in programming/scripting languages such as Python, PowerShell, Bash, C#, or Java.

• Expert in Offensive Security Tools & Frameworks: Experience with tools like Bloodhound, TinyShell, and other C2 frameworks. Strong understanding of common exploitation tools and methodologies.

• Leadership & Mentorship: Proven ability to manage and guide teams, balancing workloads, fostering growth, and ensuring high standards of work.

• Communication Skills: Excellent written and verbal communication skills, with the ability to explain complex security concepts to a range of audiences, from technical experts to business executives.

• Relevant Certifications: Industry-recognized certifications such as OSCP, OSCE, CREST, or similar credentials.

• Willingness to Travel: Ability to travel internationally as required by project and client needs.

Preferred Experience & Skills:

• Custom Tool Development: Experience with creating or modifying tools to meet the specific needs of security assessments.

• Regulatory Knowledge: Familiarity with global cybersecurity laws, compliance frameworks, and their implications for testing and reporting.

• Advisory & Threat Modeling: Experience facilitating risk workshops, threat modeling sessions, or providing strategic cybersecurity advisory services to clients.

In this role, you will be an essential part of the team, balancing hands-on technical leadership with key client-facing responsibilities. You will contribute to strengthening internal capabilities, drive improvements in methodology, and directly impact the success of both your team and the broader business. This position offers the opportunity to make a significant impact on client outcomes and to establish yourself as a leader in the cybersecurity space.

Feel free to reach out to Sheralynn Tjioe at SheralynnT@charterhouse.com.sg for more details.

Reg. No. R1878306

EA License no.: 16S8066

Only shortlisted applicants will be notified.