Leadership for pentest teams under delivery pressure

For owners and leaders of penetration testing practices.

Repeated report rework, staff turnover and overloaded senior testers put client commitments and delivery capacity under pressure.

Simon Chapman brings more than 25 years in offensive security as a technical practitioner, leader and pentest business co-founder. He investigates the causes, takes agreed leadership responsibility and develops consultants through the work that needs to improve.

Portrait of Simon Chapman

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.

Look at the work behind the symptoms.

The cost appears in missed commitments, repeated effort and experienced people with too little time to support the team.

Reports keep returning to QA

Repeated corrections consume review time and delay client delivery. The cause may sit in evidence, expectations or the support available during testing.

Senior testers keep rescuing delivery

Unplanned scoping, review and client support compete with their own booked engagements. That effort needs to be visible in the delivery allocation.

People leave faster than you can develop them

Recruitment keeps replacing lost capacity. Examine why capable people feel unsupported before expecting another hire to restore stability.

Sales commitments exceed capacity

Missing prerequisites and unrealistic allocations reach testers as urgent problems. Rework and rescheduling consume time the quote did not allow for.

Make the decision and its owner clear.

The response should fit the evidence, the team's commitments and the authority available to make a change.

Investigate the cause.

Examine actual reports, delivery records and conversations with the people involved. Test competing explanations before choosing a response.

Take agreed responsibility.

Define the decisions Simon will own, the authority and time available, and the actions that remain with your managers.

Review what changes.

Agree evidence of progress and a review point. Check subsequent work, address what remains unresolved and develop internal ownership.

Start with the situation your team is facing.

A conversation can establish the right starting point. You do not need to complete the scorecard or buy a diagnostic before discussing leadership or development support.

Diagnose

Establish what is driving the pressure.

Use a focused review of actual work to test explanations and decide which changes deserve attention.

Develop

Help consultants apply their skills.

Coach testers during live work and review their next report or client explanation to assess what they can handle independently.

Lead

Give leadership decisions an owner.

Assign part-time responsibility for defined delivery work while developing leaders within the team.

Understand the practice behind the investment.

Similar service names can conceal different coverage, effort and margin assumptions. Examine delivery capacity, specialist practices and key-person dependencies before deciding how the teams should operate together.

Explore acquisition and integration support →

Shaping offensive security integration for an investor-backed group →

Choose where to investigate. Review what changes.

Start with a self-assessment.

The free scorecard uses your assessment of the team's practices to identify areas worth investigating. A diagnostic then tests explanations against actual work and conversations.

Take the optional scorecard →

Use delivery evidence over time.

The performance framework helps you choose measures for a specific problem and assess whether a change is helping. It includes definitions and clearly labelled worked examples.

Explore the performance framework →

What needs to change for delivery to work?

Tell us where the pressure is building, what it is costing the team and what you have already tried. We can discuss the appropriate support.