Technical Director of Offensive Security (Consulting)

Company Overview
Established London-based cyber security consultancy delivering technical assurance, penetration testing, and information security services to a broad range of clients across multiple sectors.

The organisation is CREST accredited, CHECK accredited, and Cyber Essentials Plus certified, with a strong reputation for high-quality technical delivery across assurance, penetration testing, and security advisory services.

The business is relatively lean (c. 10–15 people), with a multi-million-pound turnover, meaning this is a hands-on leadership role with direct involvement in delivery rather than a purely managerial position.

Role Overview
The Head of Penetration Testing will lead and develop the organisation’s penetration testing capability, owning both technical delivery and team leadership.

This role combines hands-on technical oversight with people leadership, client engagement, and practice development. The successful candidate will act as a senior technical authority across engagements, ensuring delivery quality, consistency, and alignment with CREST and CHECK standards.

You will also support pre-sales activities, scoping, and client discussions, but the primary focus is on delivery excellence, technical leadership, and building a high-performing penetration testing function.

This role is well suited to an experienced Senior / Principal Penetration Tester, CHECK Team Leader, or Penetration Testing Manager looking to step into a broader leadership position with influence over delivery, methodology, and client advisory.

Key Responsibilities

Lead and manage the penetration testing team across multiple client engagements
Oversee delivery of web application, infrastructure, API, cloud, mobile, and red team-style testing
Act as the senior technical point of contact for clients throughout the engagement lifecycle
Support scoping, pre-sales discussions, and proposal development
Ensure all testing delivery meets high technical standards and aligns with CREST / CHECK requirements
Review technical reports and maintain consistency and quality across deliverables
Mentor and develop consultants within the penetration testing team
Contribute to the development of internal methodologies, tooling, and best practices
Support the growth of the penetration testing practice through trusted technical advisory
Work closely with senior leadership on capability planning, resourcing, and delivery priorities

Key Experience

Strong background in penetration testing within a consultancy environment
Experience leading technical engagements and managing client relationships
CREST, CHECK Team Leader, CHECK Team Member, OSCP, OSCE, OSEP, or equivalent certifications preferred
Strong understanding of CREST / CHECK methodologies and delivery standards
Experience reviewing technical reports and maintaining quality assurance standards
Proven ability to mentor, manage, and develop technical consultants
Comfortable engaging in pre-sales, scoping, and client-facing technical discussions
Strong communication skills with the ability to act as a trusted technical advisor
Hands-on technical credibility across areas such as web, infrastructure, API, cloud, or red team testing

Ideal Profile
The ideal candidate is a highly credible penetration tester who has either moved into, or is ready to move into, a broader leadership role.

They should remain technically grounded while being confident, engaging with clients, shaping engagements, and providing trusted technical direction. This is not a purely commercial role, but it does require strong client interaction skills and the ability to translate technical assurance into clear business value.

The successful individual will play a key role in maintaining delivery excellence, developing the team, and strengthening the organisation’s penetration testing capability.