Penetration Testing Lead

Software Secured

103d

About The Position

We’re looking for a Penetration Testing Lead to oversee day-to-day pentesting and delivery across our offensive security services while remaining actively hands-on. This is not a purely managerial role. You’ll continue to lead and execute your own penetration testing engagements, contribute directly to complex assessments, and stay close to the technical details that define high-quality penetration testing and other related work. You’ll manage and mentor a team of elite pentesters and security engineers, ensure every engagement meets our standards for depth and accuracy, and act as the technical owner for complex client engagements. This role sits at the intersection of hands-on offensive security, people leadership, and delivery excellence. You’ll work closely with Sales, Product, and Leadership to support scoping, improve delivery processes, and help evolve our service offerings as the business scales.

Requirements

6-8+ years in offensive security with strong hands-on experience in penetration testing, red teaming, or related domains.
2-3+ years in a technical leadership or management role within a consultancy or internal security team.
Proven ability to personally execute high-quality penetration testing engagements, not just manage them.
Proven experience managing client engagements end-to-end in a professional services environment.
Strong understanding of manual testing methodologies and frameworks, including OWASP, ASVS, WSTG, and NIST 800.
Working knowledge of compliance and audit contexts, including SOC 2, ISO 27001, and PCI DSS, and how offensive testing maps to them.
Ability to balance hands-on technical delivery with people leadership, quality ownership, and delivery management.
Clear, confident communicator with engineers, executives, and non-technical stakeholders.
Bias toward action, accountability, and high-quality outcomes.

Nice To Haves

Experience working with SaaS, FinTech, or HealthTech companies.
Familiarity with PTaaS or portal-driven delivery models.
Offensive security certifications such as OSCP, OSEP, OSCE, or equivalent.

Responsibilities

Manage and execute offensive security engagements
Personally lead and execute penetration testing engagements across web applications, APIs, cloud environments, networks, and other offensive security service lines.
Oversee and contribute to penetration tests, red team activities, and advanced security assessments.
Act as the technical escalation point for complex findings, edge cases, and client questions.
Stay close enough to the work to challenge assumptions, validate findings, and model strong testing methodology for the team.
Lead and mentor the offensive security team
Manage a team of pentesters and security engineers, providing technical guidance, feedback, and career development.
Mentor team members through hands-on review of methodology, findings, reports, and client communication.
Foster a culture of learning, curiosity, accountability, and high professional standards.
Ensure delivery quality and consistency
Own engagement scoping, execution quality, and reporting standards.
Ensure findings are accurate, reproducible, risk-focused, and actionable for engineering and compliance teams.
Review and improve reports so they meet a high bar for technical depth, clarity, and client readiness.
Help ensure delivery remains consistent across engagements, regardless of tester, client size, or service line.
Support sales and pre-sales efforts
Partner with Sales on technical discovery calls, scoping discussions, and proposal input.
Help prospects understand real-world risk, testing depth, and value beyond checkbox compliance.
Bring practical, hands-on testing experience into scoping conversations so engagements are realistic, valuable, and properly structured.
Improve delivery operations
Track and improve key delivery metrics, including SLA adherence, retesting turnaround, utilization, client satisfaction, and reporting quality.
Identify bottlenecks and continuously refine delivery processes and tooling.
Balance operational oversight with direct participation in billable technical delivery.
Contribute to service evolution
Provide hands-on input into the design and refinement of service lines such as Red Teaming, AI/LLM testing, Secure Code Review, IoT, and other emerging areas.
Help operationalize new offerings by defining scope, methodology, delivery standards, and quality expectations.
Use direct engagement experience to improve how services are packaged, delivered, and explained to clients.