Penetration testing, security assessments, and advisory services for mid-market companies. Compliance-ready. Senior-led. On your timeline.
Led by Brendon McCaulley, CISSP · 20 years in security · Active CISO
Most firms quote 4–6 weeks. We scope tightly and deliver in days — so you hit your compliance deadlines without the scramble.
Enterprise-grade methodology without the enterprise price tag. Transparent pricing starting at $5,000.
Every engagement is led personally by our founder. You know exactly who’s testing your systems and how to reach them.
Trailhead Security is built for companies like yours.
We deliver the same quality of work that enterprise security teams commission from the top firms, at pricing mid-market companies can afford, on timelines that work for compliance cycles.
OWASP Top 10, business logic, multi-role authorization. 2–5 days.
Learn more →External perimeter, internal network, AWS/Azure/GCP configurations. 2–7 days.
Learn more →PCI-DSS Req 11.4, SOC 2 CC7, HIPAA. Attestation-ready reports. vCISO available.
Learn more →Our AI-assisted platform automates discovery and normalizes findings. Every finding is reviewed by a senior analyst. Speed without shortcuts.
Brendon McCaulley, CISSP, leads every engagement personally. Not a project manager. Not a junior analyst.
Every report ships with compliance mapping to your framework. PCI-DSS, SOC 2, HIPAA, NIST. Standard, not an add-on.
Once you've fixed the findings, we re-test at no charge within 90 days. Most firms bill for retests. We don't.
PCI compliance, payment data security, regulatory audits. We know this environment. Brendon runs security at a payment processor.
HIPAA compliance, patient data protection, cyber insurance requirements. Reports formatted for your auditor.
SOC 2 readiness, customer security questionnaires, VC diligence requests. We've seen what your enterprise customers are asking for.
Typical Client: 50–500 employees · $5K–$40K per engagement · Ready to go now.
Every engagement is led personally by our founder — Brendon McCaulley, CISSP, with 20 years in security and 10 years as a CISO. Not a project manager. Not a junior analyst.
Transparent, fixed-rate engagements starting at $5,000. Proposals within 48 hours of your scoping call.