Fractional Offensive Security Leadership

Give defined leadership decisions an experienced owner while developing the people who will carry the team forward.

ForOwners and practice leaders managing delivery pressure or change.
The workPart-time responsibility with agreed authority and availability.
ProgressMore dependable delivery and responsibilities transferred when people are ready.
Fractional Offensive Security Leadership

Balance commitments, support and standards.

A team under pressure still has client commitments to meet. Simon examines where scope, scheduling and review expectations leave people unable to deliver those commitments reliably.

Some decisions require senior expertise. Others can move to team leads through agreed standards and supervised practice. Reducing senior involvement is useful only when quality holds and uncertain cases still escalate.

Define what Simon will own.

The engagement assigns recurring leadership responsibilities, decision authority and available time. The remit may cover scoping decisions, delivery quality, supervision or developing team leads.

Internal managers retain the responsibilities agreed at the outset. The arrangement names who handles urgent issues, approves commitments and provides cover between scheduled sessions.

  • Decisions and actions owned by Simon.
  • Responsibilities retained by managers and team leads.
  • Access to delivery records and the people doing the work.
  • Availability, escalation and cover.
  • A starting position, evidence of progress and agreed review dates.

Make the support fit the work being sold.

Review and coaching need an allocation alongside testing. Sales and delivery must resolve coverage, access and effort assumptions before those assumptions become urgent problems for the tester.

Shared reporting expectations give reviewers a basis for explaining material defects. Support also comes with clear professional expectations for client communication and delivery.

See how AC/DC makes QA expectations explicit

Build ownership within the team.

Choose measures that relate to the remit: recurring QA defects, unplanned senior intervention, readiness at the start of engagements or decisions handled by the agreed owner. Use a baseline and review dates suited to the available work.

At each review, examine what changed and what remains unresolved. Adjust the intervention where needed and transfer responsibilities as internal leaders demonstrate they can handle them. The aim is for agreed practices to continue between, and beyond, Simon's involvement.

Explore the performance measures

Reducing dependence on senior pentest consultants

A confidential advisory engagement with a growing cyber security consultancy's offensive security function of approximately 20 testers.

This engagement combined operational diagnosis with advisory leadership and manager coaching. Internal managers retained day-to-day authority throughout.

The problem
Delivery and management practices were struggling to keep pace with growth. Sales and scheduling staff chased readiness, while senior technical consultants repeatedly stepped in to resolve client and delivery problems.
The judgment
The friction between teams came from unclear ownership and boundaries. Improving delivery required a shared understanding of responsibilities and stronger internal management.
Simon's responsibility
Simon led the diagnosis, developed a working maturity model, clarified consulting expectations and coached managers. Internal leadership retained responsibility for the management structure and day-to-day decisions.
Read the case study

Less pressure on senior consultants

By the end of an approximately four-month engagement, senior technical consultants were carrying less of the load from client friction and delivery problems.

More effective internal managers

Managers became more visible, took clearer ownership and handled issues that had previously escalated to senior technical staff.

A basis for continued development

The team gained a working maturity model and consulting skills framework to guide further improvement.

Simon's account of an advisory engagement, based on operational observations. The client is anonymised for confidentiality.

Stabilising a pentest team and developing its next leaders

A confidential engagement with a penetration testing company of approximately 20 testers.

The problem
Frequent resignations, inconsistent quality and fragmented communication left capable testers feeling unsupported as work continued to be booked.
The judgment
Further senior recruitment would struggle to succeed unless the conditions in which the team worked changed.
Simon's responsibility
Simon headed the testing function and became the main leadership contact for scheduling, scoping and quality while establishing clearer support and standards.
Read the case study

Greater stability

Voluntary resignations fell from roughly one per month to two during a subsequent twelve-month period.

Broader contribution

More testers supported presales, scoping and a wider range of technical engagements.

Internal leadership

Senior team members began taking on leadership responsibilities, with Simon's involvement reducing from four days a week to two.

An account of Simon's engagement, with the client anonymised. The initial resignation rate is approximate, and work to develop the business continues.

Read about the delivery work involved.

These articles work through reporting and management decisions relevant to the service.

What fractional offensive security leadership actually means

Fractional offensive security leadership means giving an experienced person recurring, part-time responsibility for agreed parts of a testing function. The engagement should specify which decisions they can make and what remains with internal managers. It suits a team with defined leadership work that can be handled within the available time and authority.

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How to measure penetration testing team performance

Measure pentest team performance using project and QA records alongside utilisation. Define each measure consistently and read related results together, allowing for engagement complexity and staffing changes. Start with a delivery problem the team needs to resolve, select measures that help explain it and review whether an agreed change improves the work.

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Why senior pentesters become the delivery bottleneck

Senior pentesters become bottlenecks when routine delivery decisions keep reaching the same people alongside work that needs their specialist experience. Review the reasons for those requests and the time they consume. Transfer recurring decisions through worked examples and supervised practice, while retaining a clear route for uncertain or sensitive cases.

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Which decisions keep coming back to the same people?

We can discuss the leadership responsibilities, time and authority needed to address the pressure.