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
Traditional security testing has three problems that mid-market companies absorb every year.
Traditional firms quote 4-6 weeks. Your compliance deadline doesn't care about their delivery schedule.
Big firms charge $50K-$100K and route your engagement to junior staff. The senior talent goes to their largest accounts.
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.
We deliver the same quality of work that enterprise security teams commission from the top firms, at pricing mid-market companies can afford.
OWASP Top 10, business logic flaws, multi-role authorization, GraphQL. Actionable findings with proof-of-concept.
External perimeter, internal network, AWS/Azure/GCP configurations. Misconfigurations that lead to real access.
Kerberoasting, pass-the-hash, LDAP enumeration, NTLM relay. Attack path analysis from workstation to domain admin.
PCI-DSS Req 11.4, SOC 2 CC7, HIPAA. Attestation-ready reports your auditor can use directly.
Fractional CISO services: security program buildout, vendor risk reviews, incident response planning, board-level reporting.
Credential harvesting simulations, pretexting campaigns, employee awareness baselining. Scope agreed upfront.
Four commitments we make on every engagement.
AI-assisted tooling (Spectre) automates discovery and normalizes findings. Every finding is reviewed by a senior analyst before it reaches you. Speed without shortcuts.
Brendon McCaulley, CISSP, leads every engagement personally. Not a project manager. Not a junior analyst. The person who built the tooling runs the test.
Every report ships with a compliance mapping to your framework (PCI-DSS, SOC 2, HIPAA, NIST). Standard in every engagement, 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.
No anonymous testers. No handoffs to junior staff. One person owns your engagement start to finish.
Founder and Principal Security Consultant
"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."
Starting rates. Final pricing based on scope, systems in scope, and engagement type. Proposals within 48 hours of your scoping call.
All engagements include a written scope of work and rules of engagement before any testing begins. Free retest within 90 days of report delivery.
Send us a note. We'll schedule a 30-minute scoping call and have a proposal to you within 48 hours.
hello@trailheadsecurity.com