Know Where You Stand.

Penetration testing, security assessments, and advisory services for mid-market companies. Compliance-ready. Senior-led. On your timeline.

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Led by Brendon McCaulley, CISSP · 20 years in security · Active CISO

Security Assessments Should Work on Your Timeline, Not Theirs

Days, Not Weeks

Most firms quote 4–6 weeks. We scope tightly and deliver in days — so you hit your compliance deadlines without the scramble.

Mid-Market Pricing

Enterprise-grade methodology without the enterprise price tag. Transparent pricing starting at $5,000.

One Tester. One Relationship.

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.

Security Assessments Built for Mid-Market Companies

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.

Web App & API Testing

OWASP Top 10, business logic, multi-role authorization. 2–5 days.

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Network & Cloud Assessments

External perimeter, internal network, AWS/Azure/GCP configurations. 2–7 days.

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Compliance Testing & Advisory

PCI-DSS Req 11.4, SOC 2 CC7, HIPAA. Attestation-ready reports. vCISO available.

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What Makes Trailhead Different

2–3

Day Delivery

Our AI-assisted platform automates discovery and normalizes findings. Every finding is reviewed by a senior analyst. Speed without shortcuts.

1

Senior Lead, Every Engagement

Brendon McCaulley, CISSP, leads every engagement personally. Not a project manager. Not a junior analyst.

✓

Compliance-Ready Output

Every report ships with compliance mapping to your framework. PCI-DSS, SOC 2, HIPAA, NIST. Standard, not an add-on.

$0

Free Retest Included

Once you've fixed the findings, we re-test at no charge within 90 days. Most firms bill for retests. We don't.

Built for Financial Services, Healthcare, and SaaS

Financial Services & Fintech

PCI compliance, payment data security, regulatory audits. We know this environment. Brendon runs security at a payment processor.

Healthcare

HIPAA compliance, patient data protection, cyber insurance requirements. Reports formatted for your auditor.

SaaS Companies

SOC 2 readiness, customer security questionnaires, VC diligence requests. We've seen what your enterprise customers are asking for.

50–500 employees · $5K–$40K per engagement · Ready to go now.

You Know Who You're Working With

Brendon McCaulley, CISSP — Founder, Trailhead Security

Brendon McCaulley, CISSP

20 years in information security. 10 years as a CISO. Brendon has built and run security programs at payment processors, health tech companies, and financial services firms. He is currently the active CISO at a payment processor in the Dallas-Fort Worth area.

"I built Trailhead because mid-market companies deserve the same quality of security assessment that Fortune 500 companies get. Not a watered-down version. Not a crowdsourced stranger. The real thing, at a price you can defend to your CFO."
  • CISSP certified
  • Active CISO — fintech / payment processing
  • Former security leadership at Heartland, Optum/VPay
  • ISSA North Texas chapter leadership
  • Speaker at FutureCon
  • Texas A&M BBA, SMU MBA

Straightforward Pricing. No Surprise SOWs.

Web App Pen Test

$5,000
starting at

External Network

$5,000
starting at

PCI Compliance Package

$20,000
starting at

vCISO Advisory

$3,000
per month

Most engagements deliver in 2–5 days. Proposals within 48 hours of your scoping call.

Get a Scoping Call

Ready to See What's Exposed?

We'll scope your engagement in 30 minutes and have a proposal to you within 48 hours.

Schedule a Scoping Call