Penetration Testing for Startups: When to Get Your First Test, Cost, and Types
A founder’s guide on when to get a pen test, what it costs, the types available, and what to do with findings.
As you scale, security and compliance are key to earning trust from buyers, especially if you sell to mid-market and enterprise businesses. For many startups, the first step on the ladder is SOC 2, but it's often followed closely by penetration testing. Generally speaking, if a buyer wants to see your SOC 2 report, they'll expect a penetration test in tandem.
What Is a Penetration Test?
A penetration test mimics a real-world cyber attack. It's a controlled way to test how your environment stands up to an attempt to break in and exploit any vulnerabilities. You're essentially hiring a team to find any security flaws before real hackers do.
By completing a penetration test, you can assure buyers that your system is built to safeguard data and meet compliance requirements. A tester (or AI) will scan for vulnerabilities before probing to see what, if anything, may be exploitable. Then, if any weaknesses are found, the tester will try to break in. A penetration test will generally cover your SaaS application, any APIs, and authentication flows.
Whereas a SOC 2 Type I report will show a snapshot of your controls and a SOC 2 Type II will show those controls operating effectively, a penetration test will put those controls to the test to see if there are any vulnerabilities a rogue attacker could exploit.
Do Startups Need a Pen Test for SOC 2?
A penetration test isn't a formal requirement for SOC 2 Type I or Type II. The security criteria can be met by implementing controls and vulnerability scanning, so you can certainly achieve SOC 2 without a penetration test.
However, a penetration test is almost always worth it for any company pursuing SOC 2. The majority of enterprise customers that request your SOC 2 will also expect to see a recent penetration test alongside it.
When Should a Startup Get Its First Pen Test?
For most startups it makes sense to tackle SOC 2 and penetration testing in tandem. By the time you're looking to serve enterprise customers, your product and security procedures are likely stabilized enough to test meaningfully.
Testing too early can waste precious time and money. If your product is changing every week and you're still figuring things out, the penetration test findings will likely go stale before anyone requests to see them.
A startup's first penetration test is usually prompted by one of the following:
- An enterprise prospect's security review
- A SOC 2 auditor requesting a test
- A major product launch or feature
- Changes to how you process payments or handle authentication
Here's a quick overview of when a penetration test makes sense for a startup:
If you're doing SOC 2 Type II, run the pen test early in your observation window. That leaves time to fix what it finds and retest before the report closes.
Once you've completed your first test, you should plan on running one annually or after any material change to your product or environment.
What's the Difference Between a Vulnerability Scan and a Penetration Test?
A vulnerability scan is an automated, high-level scan that attempts to uncover potential security flaws. Whereas a penetration test is a detailed, often human-led, attempt to gain access to a system and exploit any vulnerabilities.
What Type of Pen Test Do Startups Need?
There are different types of penetration tests available. Automated pen tests are often more advanced vulnerability scans. They're useful for continuous coverage but don't seek to exploit any gaps, and often won't meet what a buyer is looking for if they request a pen test.
There are also new AI pen testing tools like RunSybil and XBOW which offer agentic testing where they actively probe and try to exploit what they find, and they can run on a more continuous basis.
When it comes to traditional pen testing, tests fall under three categories and the main difference is how much information the tester has access to before starting:
- Black box testing: The tester has no knowledge about your environment and acts as an outside hacker would.
- Gray box testing: The tester knows some information about your environment like IP addresses, testing accounts, API docs, and architecture details.
- White box testing: The tester has full knowledge and network access.
For most startups getting their first pen test, gray box testing tends to give you the most useful information for the money. With gray box testing, the tester is spending time exploring vulnerabilities and looking for weaknesses rather than on reconnaissance and gaining initial access.
How Much Does a Startup Pen Test Cost?
A basic pen test for a single web application with external access will generally cost roughly $3,000 to $5,000. The cost ramps up the more you want to test. If you add in an API, cloud configuration, and more applications, the cost can reach more than $10,000. But these are ballpark estimates and the cost largely depends on where you're starting from and the scope.
What Happens After a Pen Test?
You don't pass or fail a pen test. The report comes back with a list of findings with severity noted alongside each. Post-test, your job is to close any serious vulnerabilities. Then once any of the critical or high issues are fixed, you should retest or get an addendum showing what's been closed so you have proof to share with your auditor or enterprise buyer that you've fixed the issues.
As I mentioned earlier, if you're working towards SOC 2 Type II, you should run your pen test near the start of your observation period so there's time to remediate any issues before the period ends.
How to Choose the Right Pen Test Partner
The first thing to look for is a partner who is keen to match the test to your stage and connect the test back to your compliance and sales goals. A seed-stage business doesn't need a pen test designed to simulate attacks from nation-state actors. On the flip side, a seed-stage business selling to enterprise also doesn't need a dressed-up vulnerability scan.
A startup-friendly penetration test should involve real exploitation, whether human-led or agentic, rather than scanning alone. And, ideally, you want a partner that can offer remediation support on the back of the test, not just a PDF report with no plan on how to tackle any vulnerabilities.
The #1 thing you should ask any prospective partner is how the specific test they recommended will map to what your auditor or enterprise buyer is going to ask for. A partner that understands the compliance and sales context surrounding the test will be best positioned to deliver what you need.
At Workstreet, we offer right-sized penetration testing that's scoped to your company stage and needs. We can also work with your team all the way from scoping to remediation.
How to Prepare for Your First Pen Test
Good preparation means you'll get what you need out of your penetration test. As you head into your first test, here's what you and your testing partner should be considering:
- Scope: Which applications, APIs, and environments will be tested.
- The goal: Is the test part of an upcoming audit (ISO 27001, HIPAA, SOC 2), to help streamline enterprise procurement, or to simply test your environment after significant changes.
- Type of test: Gray box is often the choice for a startup's first test.
- Documentation: If you're going for a gray box test, you'll need to prep API docs and architecture notes to assist the tester.
- Remediation: Who will handle remediation and what will their process be.
Where a Pen Test Pays Off for Startups
Penetration testing is a technical exercise, but for an early-stage startup it pays off in two ways. It helps build trust by proving your systems are built to handle sensitive data and protected against cyber attacks and bad actors. It also helps clear security reviews and unblock your pipeline so you can close more enterprise customers.
Your first penetration test should be right-sized, involve manual or agentic probing to find vulnerabilities, and be tied to a real business outcome. It should focus on the parts of your business buyers (or auditors) care about most, like applications, authentication, and APIs. And give your team a clear understanding of how your security controls stand up to scrutiny and what fixes you might need to make.
If you're working out when and how to run your first pen test, our penetration testing practice can right-size it to your stage and tie the findings into your compliance program. Talk to our team to see what it would look like for your company.
