93% of companies rely on penetration testing to meet compliance requirements and yet 67% of breaches happen due to vulnerabilities that should’ve been caught much earlier.

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So what’s going wrong?

It’s not the concept of pen testing that’s flawed. In fact, the idea originated more than 60 years ago when NASA and the NSA began proactively stress-testing early computing systems. The goal back then? To find real security flaws before attackers could exploit them.

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Fast forward to today, and pen testing has largely lost its way.

Most companies conduct tests only when an audit is approaching or when a client requests a security report.

These assessments are:

• Too late — often happening after critical vulnerabilities have lingered undetected for months.
• Too rigid — scoped months in advance, failing to account for real-time changes in infrastructure.
• Time-based, not outcome-based — with testers rewarded for hours spent, not for actual discoveries of risk.

The result? Security becomes a box-checking exercise rather than a meaningful way to reduce risk.

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When Should Pen Testing Actually Happen?

Pen testing shouldn’t be a once-a-year event. To truly protect your company, testing should be integrated throughout your development and deployment cycle.

Here’s when you should be testing:

• Before launching a new web application or service
• After major code changes or feature releases
• As part of your preparation for a compliance audit
• Or best of all: as an ongoing, adaptive security strategy

How Linda Mar Associates Approaches Pen Testing Differently

At Linda Mar Associates, we believe security shouldn’t be reactive. That’s why we’ve reimagined the pen testing model for startups and high-growth companies.

Here’s how we’re different:

• Outcome-Based Testing: We focus on discovering real risk, not logging billable hours.
• On-Demand Security: Our model adapts to your evolving infrastructure and threat landscape.
• LatAm Pricing, Silicon Valley Expertise: High-impact security, delivered efficiently.

We don’t believe security is a one-time event. It’s a continuous, evolving process—and your testing strategy should reflect that.

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