If you're shopping for a penetration testing provider for the first time, the market can be confusing. Prices range from $1,500 to $100,000+. Some firms are solo consultants; others are publicly traded companies. Some promise automated scans; others send former military operators to physically break into your building.

How do you know which firm is right for your business? Here are seven things to evaluate before you sign a contract.

1. Certifications Matter More Than Company Size

The single best indicator of testing quality is the certifications held by the person who will actually conduct your test. The industry gold standard is the OSCP (Offensive Security Certified Professional), a hands-on exam that requires candidates to break into multiple systems within a 24-hour window. Other respected credentials include CRTO (Certified Red Team Operator), OSEP, and GPEN.

Ask specifically: Who will conduct my test, and what certifications do they hold? At many larger firms, a senior consultant sells the engagement and a junior analyst executes it. There's nothing inherently wrong with that model, but you should know who's doing the work. At Trident Shell, every engagement is led by an OSCP and CRTO certified principal.

2. Methodology Should Be Transparent

A reputable firm will explain their methodology upfront. Most follow frameworks like OWASP for web applications, PTES (Penetration Testing Execution Standard), or NIST SP 800-115 for general testing. Ask for a scoping document that outlines:

  • What systems and networks are in scope
  • What testing methods will be used (automated + manual)
  • What is explicitly excluded
  • How critical findings are communicated during testing
  • What deliverables you'll receive

If a provider can't clearly explain their process before you sign, that's a red flag.

3. Report Quality Is the Deliverable

You're not paying for the test itself. You're paying for the report. A good penetration test report should include an executive summary that non-technical stakeholders can understand, detailed technical findings with evidence (screenshots, proof of concept), risk ratings aligned to a recognized framework (CVSS, for example), and specific, actionable remediation guidance.

Ask to see a sample report before signing. If the sample is just a list of vulnerability scanner outputs with no analysis, you're paying for a scan, not a pentest. The difference matters, especially for cyber insurance and compliance requirements.

4. Compliance Expertise Saves You Time

If you need a penetration test for a specific compliance requirement, make sure the firm has experience with that framework. A general-purpose pentest and a HIPAA-focused assessment have different scoping requirements, reporting formats, and deliverables.

The right firm will know what your auditor or underwriter expects to see and format the report accordingly. This saves you from paying for a test that doesn't actually satisfy your compliance requirement. Common frameworks that require or recommend penetration testing include cyber insurance policies, HIPAA, SOC 2, and PCI-DSS.

5. Pricing Should Be Transparent

Most penetration testing firms don't publish their prices. That's by design. Enterprise firms charge $15,000 to $50,000 for assessments that may take two to four weeks. Some firms charge by the hour, others by the project.

For SMBs, look for fixed-price engagements with clear scoping. You should know before signing exactly what you'll pay, what's included, and what would trigger additional costs. Trident Shell publishes pricing openly: assessments start at $1,500 for a compliance quick-start, $2,500 for a full assessment, and $4,500 for an annual program. No hidden fees, no scope surprises.

6. Communication Should Be Direct

During a penetration test, the tester may discover a critical vulnerability that requires immediate attention. How quickly will they tell you? Through what channel? Some firms have a 24-hour notification policy for critical findings, meaning they'll alert you the same day rather than waiting for the final report.

Also consider who you'll be talking to throughout the engagement. If your primary contact is a project manager who relays questions to the tester, that adds delays and potential for miscommunication. Direct access to the tester conducting your assessment leads to faster, more accurate communication.

7. Retesting Policy Matters

A penetration test isn't complete when the report is delivered. It's complete when the vulnerabilities are fixed. Ask whether the firm offers retesting after you've implemented their recommendations. Some firms include one round of retesting in their price; others charge separately.

Retesting verifies that your remediation efforts actually closed the gaps. Without it, you're relying on assumptions. This is especially important for compliance purposes, where auditors may ask for evidence that identified issues were resolved.

Red Flags to Watch For

  • No scoping call: A firm that quotes a price without understanding your environment is guessing.
  • Scanner-only results: If the deliverable looks like automated tool output with no manual analysis, you overpaid.
  • No liability insurance: Professional liability (E&O) insurance protects both parties. Ask for proof.
  • Vague timelines: A professional firm should commit to a delivery date.
  • Reluctance to share credentials: If they won't tell you who's testing and what certifications they hold, walk away.

Making Your Decision

The right penetration testing company for a 50-person business looks different from the right company for a Fortune 500. For small and mid-sized businesses, prioritize: relevant certifications (OSCP minimum), compliance expertise for your specific requirement, transparent pricing, direct communication with the tester, and a clear retesting policy.

If you're evaluating providers and want to understand how Trident Shell approaches these criteria, reach out for a free 15-minute scoping call. We'll walk through your environment, your compliance needs, and give you a fixed-price proposal the same day.