Know Where You Stand. In Days, Not Months.

Penetration testing, security assessments, and advisory services for mid-market companies. Reports in hand within 2-3 days. Compliance-ready. Senior-led.

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

Most Pen Tests Take 4–6 Weeks. Yours Is Probably Late.

Slow Timelines

Traditional firms quote 4–6 week delivery. Your audit deadline doesn't care.

Enterprise Pricing

Big firms charge $50K–$100K. The quality goes to their larger accounts anyway.

Anonymous Testers

Crowdsourced platforms send anonymous testers. You get whoever's available.

Trailhead Security is a different model.

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