How to Buy a Penetration Test: A Practical Guide for Family Offices

A penetration test (or “pentest”) is a controlled exercise where security professionals simulate real-world attacks against your systems, people, and processes to identify how an attacker could gain access or cause harm. Unlike simple vulnerability scans, a true penetration test mimics how attacks actually occur by combining technical vulnerabilities, human behavior, and gaps in controls.

For many family offices, a pentest feels like the “right thing to do”, but can also feel like a black-box exercise. Proposals vary widely, pricing is inconsistent, and the deliverables often look highly technical. The result? Too many offices spend money on testing that doesn’t meaningfully reduce risk.

The goal of a pentest is to identify realistic, exploitable weaknesses and fix them. Done right, it’s one of the highest-value security investments you can make.

Here’s how to get it right.

1. Start with Scope

Before engaging firms, define what you actually need tested. For most family offices the highest-risk areas are:

• External perimeter (internet-facing systems)
• Email and phishing susceptibility
• Remote access tools (VPN, remote desktop, etc.)
• Internal systems like SharePoint, accounting, payroll, investment platforms

Just as important: think in terms of layers of control, not just systems. For example:

• Phishing should test email filtering, user awareness, MFA, endpoint protection
• Technical testing should test the firewall, authentication, monitoring and alerting

A well-scoped engagement tests whether each layer of defense actually works together in practice.

2. Include Social Engineering Because Attackers Do

Many penetration tests focus purely on technology. Real attackers don’t.

For family offices, phishing and social engineering are often the highest-probability threats, given:

• Small FO teams have broad access
• Actual or perceived high-value transactions
• Frequent interaction with external advisors

At minimum, your social engineering approach should include:

• Phishing simulations (to test user behavior)
• Credential capture scenarios (to test MFA effectiveness)

Phishing tools like KnowBe4, Proofpoint, etc., are great for exposing users to common attacks. However, they stop short of testing how your layered controls perform together. A more integrated approach adds value. For example:

• Does the email filter catch the phishing attempt?
• If not, does the user recognize and report it?
• If they click, does MFA stop account compromise?
• If credentials are captured, are alerts triggered?

This type of testing provides a clearer picture of how your defenses perform as a system, not just as individual tools.

3. Understand Vulnerability Testing vs. Penetration Testing

Vulnerability testing identifies and catalogs potential technical weaknesses using automated tools, but does not exploit them. Penetration testing goes further by actively exploiting those weaknesses, often in combination, to simulate real-world attacks and demonstrate actual risk.

For family offices, you need both. Vulnerability testing should be performed frequently (even weekly) to surface issues early. Penetration testing, conducted annually, shows how a skilled attacker could chain those weaknesses together to compromise your environment.

A common pitfall is vendors presenting automated vulnerability scans as “penetration tests,” which do not reflect how real attacks occur. Here’s what to ask:

• Ask how much is manual vs. automated: A true pen test involves significant hands-on testing, not just tools.
• Look for attack paths, not just findings: Reports should show how weaknesses can be combined and exploited.
• Sanity check time and scope: Broad testing completed in a day or two is likely a scan, not a true penetration test.

4. Ask These Five Questions Before You Buy

• What exactly is in scope? Systems, domains, users, and scenarios (including phishing) should be clearly defined.
• How do you test layered controls? Look for an approach that evaluates how defenses function together and not just point-in-time findings.
• How do you prioritize findings? You want business risk, not just technical severity.
• Will you validate that fixes work? Retesting is essential.
• What does the final output look like?

It should include:

• Executive summary (plain English)
• Clear business impact
• Practical remediation steps

5. Know the Pricing

For a typical single-family office:

• External penetration test: $5,000 – $15,000
• Internal penetration test: $5,000 - $20,000
• Phishing/social engineering testing: $3,000 – $8,000
• Wireless penetration testing: $3,000 - $6,000

What affects cost:

• Scope and number of systems or users
• Inclusion of social engineering and/or wireless
• Depth of manual testing
• Retesting and level of interaction

Be cautious of low-cost options as they often rely heavily on automation and may not provide meaningful insight into how your defenses perform under real conditions.

6. Make it a Collaborative Approach…Not a “Gotcha” Exercise

The most effective penetration tests aren’t adversarial—they’re collaborative and iterative.

This approach has two important benefits:

• Align with your IT team on how controls are intended to work
• Test those controls in realistic sequences
• Provide clarity on both strengths and gaps

• Better security outcomes: You gain insight into how attacks actually succeed or fail across your environment.
• More informed investment decisions: Testing helps clarify which controls are performing, where redundancy exists, and where gaps remain.

• A short list of critical issues to address immediately
• Insight into how your defensive layers performed
• A prioritized path forward

7. Focus on Outcomes, Not the Report

A penetration test is only valuable if it leads to action. After the test, you should have:

You should always have a formal debrief with the vendor to go over the entire test.

Final Thought

Penetration testing for family offices isn’t a compliance exercise, and it shouldn’t be a technical black box. It answers the simple question: If someone targeted us, what would actually happen?

For family offices penetration testing needs to reflect how attacks really occur and how defenses actually perform together. That’s how a one-time exercise becomes a more durable security capability.