Most organizations are certified. Most organizations still get breached. The gap between what your compliance documentation claims and what your environment actually contains is where breaches live — and where Grey Security works.
The certifications are real. The auditors signed off. The dashboard is green. The breach happens anyway — three years after the last audit said everything was fine.
The offshore team accessing PHI is invisible in the SOC 2 report. The VPN account for the former employee has no expiration date. The CISO reports to the CIO, who filters what reaches the board. These are not edge cases. They are the standard condition.
Grey Security provides the assessment, offensive testing, and advisory that organizations need when they are ready to find out what their program actually looks like — not what it is certified to claim.
We assess whether your security program is functioning operationally or just on paper. We find the offshore access invisible in your SOC 2 report. The exception list that undermines your control framework. The gap between your certified posture and your operational one. The deliverable is not another compliance report. It is the truth.
Penetration tests and red team operations designed to find what an actual adversary finds — not what a compliance-scoped assessment permits. We start where attackers start: external reconnaissance, credential exposure, shadow IT, and third-party access paths outside your defined network boundary. We measure detection time alongside finding count.
Senior security leadership for organizations that need the function without the full-time headcount, or that need an independent perspective on whether their program is functioning as well as they believe it is. Includes board-level security reporting, executive risk translation, and the organizational governance work that determines whether your security function has authority independent of IT delivery pressure.
An adversarial examination of the gaps between what your certifications describe and what your operational environment contains. The systems added after the assessment window. The vendors whose access falls outside the defined scope. The offshore teams whose endpoint security is invisible in every certification document you hold. A verification that your compliance means what you think it means.
Most security assessments are filtered before they reach the board. The CISO reports to the CIO. The CIO commissioned the assessment. The findings that would embarrass IT delivery never make it to the executive team in their original form.
Grey Security operates outside your IT chain of command entirely. Our findings reach leadership unfiltered — because that is the only version of this work that is worth paying for.
The model at most advisory firms: a senior partner sells the engagement, a junior analyst runs the templated checklist, and a report is assembled from a library of pre-written findings. You get a 90-page PDF and a presentation summarizing it.
James Shariff personally leads every engagement. Two decades of DoD, healthcare, and cloud-native SaaS experience, applied directly to your environment. No subcontractors. No hand-offs. No binder-delivery model.
Compliance auditors look for documentation. Attackers look for gaps. Grey Security applies the adversarial lens — external reconnaissance, credential exposure, vendor access paths, and the offshore access your SOC 2 scope excluded — to find what a real threat actor finds.
Every finding is mapped to the relevant framework controls: HITRUST CSF, PCI DSS v4.0, SOC 2 CC criteria, HIPAA safeguards, and RMF. Audit-ready documentation and a prioritized remediation roadmap — not a generic risk rating with no path forward.
All engagements are conducted under a signed Statement of Work and Rules of Engagement. Offensive security work is authorized in writing before any testing begins. Client identities and findings are never disclosed.
"The offshore access finding alone justified the entire engagement. It was in no certification document we held. It was in the environment."
"We had passed PCI DSS v4.0 six weeks before the assessment. James found three control gaps our QSA had not tested. Two were in scope."
"The board presentation changed how our leadership understands security investment. For the first time they were looking at real risk, not compliance status."
Client identities withheld per engagement confidentiality policy.
The compliance requirements, the common gaps, and the specific failure patterns in these industries are not hypothetical. They are documented experience.
RMF, FedRAMP, CMMC. Direct experience with ATO processes, SOW gaps, and the compliance-vs-security failure mode inside defense contracting.
HIPAA, HITRUST CSF, HL7/FHIR security. Specific experience with offshore PHI access gaps that SOC 2 and HITRUST certifications do not surface.
PCI DSS v4.0, SOC 2 Type II, SEC cyber disclosure requirements. Third-party risk in payment and data processing environments.
AWS, Azure, GCP shared responsibility gaps, multi-cloud architecture, DevSecOps program assessment, and CI/CD pipeline security.
EDI processing, practice management security, insurance clearinghouse risk, and PHI handling across complex third-party ecosystems.
Security program assessment and CISO advisory for organizations whose security function reports to IT and whose board needs an honest picture of actual risk.
A direct conversation about what your environment contains, what certifications you hold, and where you suspect the gaps are. No pitch deck. No discovery questionnaire. A real conversation about your actual situation.
A signed Statement of Work and Rules of Engagement before any testing begins. Scope is defined, authorized, and documented. Offensive engagements proceed only under written authorization. No exceptions.
The work is performed directly — no subcontractors, no templated checklists. Technical testing, documentation review, and adversarial examination of the gaps between your certified posture and your operational environment.
Findings mapped to framework controls. Prioritized remediation roadmap. Executive brief that translates technical risk into business decisions. Governance documentation your legal team, board, and auditors can use.
The compliance certification described what was assessed. The adversary found what was not. The offshore team accessing production data was outside the audit scope. The VPN account for the former employee was never in the evidence package. The SOC 2 said everything was fine. The breach happened anyway.
The GreySecurity Risk Intelligence Report documents the structural failure patterns behind that gap — drawn from two decades of direct engagement inside DoD contracting, healthcare security programs, and enterprise security organizations. Eight sections. Every major breach pattern analyzed. The accountability shift that changes personal CISO exposure in 2025. And a framework for measuring the gap between your certified posture and what an adversary would actually find.
For authorized distribution only — not publicly available
The report is distributed directly to qualified clients and prospects. Request a copy to receive the full 2025 edition.
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I have spent two decades inside the environments most advisory firms only read reports about. DoD systems under ATO. Healthcare platforms handling tens of millions of patient records. Cloud-native SaaS companies with offshore development teams, shared credentials, and a SOC 2 report that covered none of it.
The pattern was the same every time. The paperwork was immaculate. The environment was exposed. The CISO was reporting to the CIO. The offshore team had PHI access the HITRUST certification never covered. The exception list had grown longer than the control framework it was supposed to support. Nobody had told the board any of this — because nobody had looked.
I started Grey Security to give organizations the honest assessment they cannot get from the firms whose model depends on delivering good news. The conversation is not always comfortable. It is always the one that needed to happen.
Most organizations are not ready for this conversation. If you are, we should talk.
Tell us what you are dealing with. We will tell you whether we can help.
We scope further by phone. This is just the introduction.