What Does Effective Red Teaming Look Like?
Offensive Security: Why Not All Programs Deliver Equal Value
Plenty of companies spend money on penetration tests or red team exercises, yet still feel little has changed in their overall security posture. The problem isn’t the concept—it’s the execution. True value comes when testing directly reflects business risks and produces insights leaders can act on.
So, what makes an offensive security program effective? And how can you tell if your organization is getting outcomes instead of just another compliance report?
Alex Cobblah Red Team Practice Lead at Maverc, shares his perspective . His approach highlights what mature, business-aligned offensive security looks like.
Building Blocks of Effective Coverage
Effective security coverage is shaped by an organization’s risk profile, industry, and the sensitivity of its data. There’s no universal playbook—every environment is unique, and your strategy should reflect your specific risks and priorities. A tiered framework can provide a useful starting template, but it must be customized to fit your business context.
For instance, a company running a mission-critical cloud application may require cloud penetration testing several times a year, while a manufacturing plant might place higher emphasis on physical security and operational technology assessments than on cloud-heavy testing.
Foundation First
Begin with the basics: threat modeling, vulnerability management, attack surface monitoring, and an appsec program with routine testing.Expand with Advanced Testing
Once the foundation is mature, add structured penetration testing of networks, applications, and cloud environments.Capstone: Adversary Simulation
The most advanced stage uses red teaming, purple teaming, and tabletop exercises to test both defenses and response against realistic adversaries.
This progression ensures each stage is strengthened before moving to the next.
Where Most Organizations Stand
Organizations vary widely in how they approach offensive security. Some are driven by compliance requirements, others by the need to keep pace with business growth and evolving threats, and a smaller group by the realities of being a high-value target. Offensive security maturity often falls into three buckets:
Minimal (Compliance-Oriented)
Meets requirements like an annual penetration test.
Focused on passing audits, not improving defenses.
Baseline (Most Common)
Semiannual pen tests across networks and applications.
Periodic assessments of critical systems such as Active Directory or MFA environments.
Provides meaningful insights but still point-in-time.
Advanced (High-Value Targets)
Continuous penetration testing and attack surface monitoring.
Bug bounty programs and active monitoring for zero-days.
Multiple red team scenarios annually to test different business units and threat models.
As organizations advance through maturity tiers, red teaming emerges as the capstone of an offensive security program. It moves beyond compliance checklists and point-in-time vulnerability testing, focusing instead on simulating real-world adversaries with defined objectives. This is where the line between average coverage and exceptional resilience becomes clear.
The 5-5-20x Framework
To keep your red team efforts aligned with business priorities, Alex recommends the 5-5-20x framework by first identifying your organization’s
5 key threats most relevant to your business (e.g., ransomware, supply chain risk)
5 likely adversaries (e.g., nation-states, cybercriminal groups, insiders)
20 critical systems (“crown jewels”) that must be protected
X lines of business that make up the overall attack surface
Build red-team exercises around combinations of those prioritized elements. Rather than broad, unfocused tests that only surface incidental findings, this focused approach produces outcomes that map to your highest-risk objectives and are easy to measure.
What Great Red Teams Deliver
Red teaming is not simply scaled-up vulnerability scanning or a relabeled penetration test. Proper red teaming is a targeted, intelligence-driven simulation of real adversaries pursuing specific objectives inside your environment. The most effective red teams illuminate your true risk posture and produce actionable insights across three areas:
Exploitable Weaknesses – vulnerabilities linked to realistic attack paths.
Detection and Response Gaps – showing how well teams and tools react.
Systemic Issues – big-picture problems like segmentation gaps or poor secrets management.
The best engagements tie findings to business risk, not just technical flaws.
Above the Line, Below the Line, Off the Cliff
The value of a red team engagement is not measured by the sheer number of vulnerabilities identified, but by how effectively those findings are connected to business risk. Organizations do not operate in a vacuum of technical flaws; they operate in a landscape where security gaps can disrupt operations, expose sensitive data, and undermine customer trust.
A mature red team program provides clarity by demonstrating:
Business-Relevant Attack Paths – how an adversary could realistically exploit weaknesses to reach critical assets.
Operational Impact – what a successful attack would mean for continuity, revenue, or reputation.
Actionable Prioritization – which remediations should be addressed first to meaningfully reduce risk.
This risk-aligned perspective transforms red teaming from a purely technical exercise into a strategic enabler. Executives gain visibility into their true threat exposure, security teams receive actionable guidance, and the organization as a whole benefits from a security roadmap that is rooted in measurable business outcomes.
In short, red teaming delivers its greatest value when it translates technical insights into business-aligned action.
Examples:
Good: A test shows how ransomware could move across hybrid infrastructure, leading to investments in segmentation.
Bad: A 90-page list of vulnerabilities with no prioritization.
Ugly: Hundreds of findings unrelated to objectives, leaving leadership lost.
The Real Measure of Success
A well-executed red team exercise should leave leadership with the ability to confidently articulate:
How adversaries could realistically compromise the organization’s most critical assets.
Where existing defenses proved effective—and where they failed.
Which corrective actions deserve immediate priority.
The true measure of success lies in clarity. An impactful red team engagement delivers unambiguous insight into security posture, translating technical findings into business-relevant outcomes.
Ultimately, the value is not just in identifying weaknesses, but in producing a prioritized, actionable roadmap that guides security investments and strengthens resilience against real-world threats.
Maverc’s Penetration Testing and Red Team services simulate real-world attacks to reveal exploitable weaknesses, validate detection and response, and align findings to business risk. We combine targeted penetration tests, adversary emulation, and purple-team collaboration to produce prioritized, actionable remediation roadmaps and executive-grade reporting—so leaders get clarity and security teams get work they can actually act on. Suscribe to our blog for more Cybersecurity tips and guides.
