Enterprise-Grade Penetration Testing. Delivered in Days.

We find the gaps in your network, web apps, and cloud before attackers do. Reports in hand within 2-5 days. Compliance-ready. Senior-led.

Led by Brendon McCaulley, CISSP  |  20 years in security  |  Former CISO  |  Active at a payment processor

Most pen tests take 4-6 weeks. Yours is probably late.

Traditional security testing has three problems that mid-market companies absorb every year.

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Timelines Don't Fit Audits

Traditional firms quote 4-6 weeks. Your compliance deadline doesn't care about their delivery schedule.

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Enterprise Pricing, Mid-Market Budget

Big firms charge $50K-$100K and route your engagement to junior staff. The senior talent goes to their largest accounts.

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Anonymous Testers

Crowdsourced platforms send whoever's available. You don't know who's on your network until after the test.

Trailhead Security is a different model.

Penetration Testing 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.

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Web App and API Testing

OWASP Top 10, business logic flaws, multi-role authorization, GraphQL. Actionable findings with proof-of-concept.

2-5 days  |  from $5,000
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Network and Cloud Assessments

External perimeter, internal network, AWS/Azure/GCP configurations. Misconfigurations that lead to real access.

2-7 days  |  from $5,000
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Active Directory and Identity

Kerberoasting, pass-the-hash, LDAP enumeration, NTLM relay. Attack path analysis from workstation to domain admin.

3-5 days  |  from $8,000
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Compliance Testing and Advisory

PCI-DSS Req 11.4, SOC 2 CC7, HIPAA. Attestation-ready reports your auditor can use directly.

2-7 days  |  from $10,000
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vCISO Advisory

Fractional CISO services: security program buildout, vendor risk reviews, incident response planning, board-level reporting.

Ongoing  |  from $3,000/month
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Phishing and Social Engineering

Credential harvesting simulations, pretexting campaigns, employee awareness baselining. Scope agreed upfront.

3-5 days  |  from $5,000

What Makes Trailhead Different

Four commitments we make on every engagement.

1

2-5 Day Delivery

AI-assisted tooling (Spectre) automates discovery and normalizes findings. Every finding is reviewed by a senior analyst before it reaches you. Speed without shortcuts.

2

Senior-Led, Every Engagement

Brendon McCaulley, CISSP, leads every engagement personally. Not a project manager. Not a junior analyst. The person who built the tooling runs the test.

3

Compliance-Ready Output

Every report ships with a compliance mapping to your framework (PCI-DSS, SOC 2, HIPAA, NIST). Standard in every engagement, not an add-on.

4

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.

You Know Who You're Working With

No anonymous testers. No handoffs to junior staff. One person owns your engagement start to finish.

👤

Brendon McCaulley, CISSP

Founder and Principal Security Consultant

  • 20 years in information security. 10 years as a CISO.
  • Background at Heartland Payment Systems, Optum/VPay, ConnexPay.
  • Active security leader at a payment processor.
  • ISSA North Texas chapter leadership.
  • Speaker at FutureCon.
  • Texas A&M BBA.
"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."

Straightforward Pricing. No Surprise SOWs.

Starting rates. Final pricing based on scope, systems in scope, and engagement type. Proposals within 48 hours of your scoping call.

Web App Pen Test

from $5,000
2-5 day delivery

External Network Assessment

from $5,000
2-5 day delivery

Active Directory Assessment

from $8,000
3-5 day delivery

PCI Compliance Package

from $20,000
Includes attestation-ready report

vCISO Advisory

from $3,000/mo
Fractional CISO engagement

All engagements include a written scope of work and rules of engagement before any testing begins. Free retest within 90 days of report delivery.

Ready to See What We Find?

Send us a note. We'll schedule a 30-minute scoping call and have a proposal to you within 48 hours.

hello@trailheadsecurity.com
Or reach out at hello@trailheadsecurity.com to get started.