Conversec · Simon Chapman

Leadership for pentest teams under delivery pressure

For owners and leaders of penetration testing practices.

Reports keep coming back from QA. Experienced testers are stretched between their own work and helping everyone else. People leave, and another hire only briefly eases the pressure.

Simon Chapman helps you understand what is happening and work through it with your team. Through retained fractional leadership, he takes on agreed responsibilities with a regular monthly commitment, drawing on more than 25 years in offensive security as a practitioner, leader and pentest business co-founder.

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From an engagement

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 judgement: 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.

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Observed results

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.

Sound familiar?

When keeping delivery moving takes too much effort.

These problems cost the team time and energy. Looking at where the work gets stuck helps us understand what would make a difference.

Reports keep coming back from QA

The same corrections hold up reports and take time from reviewers. Missing evidence, unclear expectations or too little support during testing can all play a part.

Senior testers keep rescuing delivery

Scoping queries, report rewrites and client calls land on people who already have a full testing schedule. If senior testers are spending time on this, it needs room in the schedule.

People leave faster than you can develop them

You keep recruiting, but much of the effort goes into replacing people who have left. Understanding why capable testers feel unsupported is part of making the next hire work.

The work being sold is hard to deliver

Missing access and unrealistic time allowances become urgent problems once testing starts. Your team absorbs the rework and rescheduling that the quote never allowed for.

How we work together

Understand the problem. Give people the help to resolve it.

Simon works alongside your business over an agreed period, getting to know its people and delivery practices. He stays involved as changes take hold and people within the team take on more responsibility.

Understand what is going wrong.

Simon looks at reports and delivery records with the people doing the work. That helps us check possible causes and choose a response that fits.

Be clear about who will help.

We agree which decisions Simon will make, the time and authority he needs, and what your managers will continue to handle.

See whether the change is helping.

We agree what progress would look like and when to check it. Later reports and delivery decisions show what is improving, where more help is needed and what the team can take on itself.

Finding the right help

Start with what your team is facing.

Retained fractional leadership is our main way of working with clients. Diagnostics and coaching are also available independently when you need focused help. You can discuss leadership directly, without completing a scorecard or booking a diagnostic.

Lead

Get experienced help with running the practice.

Work with Simon each month on agreed leadership responsibilities, with time to understand the business and help people within your team grow into those roles.

Fractional Leadership

Diagnose

Find out why the problem keeps coming back.

Work through reports, QA feedback and delivery records with Simon to understand what needs attention first.

Pentest Team Diagnostic

Develop

Help consultants put their skills into practice.

Help consultants think through unfamiliar problems, communicate clearly in writing and conversation, and recognise where their technical skills need further development.

Consultant Accelerator

For investors and acquiring groups

Understand the practice behind the investment.

Two practices can sell services with the same name and deliver them quite differently. Understanding the coverage, effort, specialist skills and reliance on key people helps you judge what you are acquiring and how the teams could work together.

Explore acquisition and integration support →

Shaping offensive security integration for an investor-backed group →

Tools you can use

Take a closer look at how your team works.

Where could the team use more support?

The free scorecard asks about the way your team works under pressure. Your answers highlight strengths and areas to look at more closely.

Try the free scorecard →

Is a change making delivery better?

The performance framework helps you choose measures for a problem you want to understand. Definitions and worked examples show how to read the results together and check whether a change is helping.

Explore the performance framework →

Talk it through

Where is your team feeling the pressure?

Tell us what is happening and what you have already tried. We can talk through whether ongoing leadership support would help and what Simon would take on.

Discuss your team Explore fractional leadership