The Engineered Forest: Why the Best Security Programs Are Invisible
security leadership philosophy CISO
Last week, driving through New Hampshire’s Kancamagus Highway, I stopped at a scenic overlook. An information board caught my eye. It explained how the “wild” forest around me wasn’t wild at all. Every aspect had been carefully engineered: which trees to plant, where to thin for sunlight, how to manage erosion, where to route trails. Even the logging operations over decades were intentional, shaping the forest’s composition and health. This forest that felt so natural, so effortless, was actually the product of decades of deliberate planning.
And I immediately thought about security programs.
The best security programs work exactly like that engineered forest. They feel natural. Teams barely notice them. Work flows smoothly. And most people have no idea how much intentional architecture went into making it all just… work.
Most security programs do the opposite. They’re highly visible. Bureaucratic. Blocking. Everyone knows security exists because security keeps saying no.
The Problem: Security as Speedbump
You know the pattern:
Firewall requests requiring multiple security sign-offs. A developer needs to open a port for internal service-to-service communication. Two weeks later, they’re still waiting. The project is blocked and the business is asking why engineering can’t move faster.
Security reviews for every vendor, even office furniture. Because reasons. The procurement team learns to just not tell security about things.
The checkbox of doom. I once saw a company make employees confirm every external email didn’t contain sensitive data. Every. Single. Email. Within a week, people mindlessly clicked through two dialogs. Security theater, teaching users to ignore security prompts.
The pattern: Security as gatekeepers who slow everything down and say no.
Then we wonder why nobody wants to work with us.
The Principle: Intentional Architecture
That Kancamagus forest didn’t have signs saying “NO WALKING HERE” everywhere. Forest managers designed trails that naturally guided foot traffic. They planted trees that would thrive. They even planned logging operations decades in advance. The system made doing the right thing the easy thing.
Good security works the same way.
Security says “yes” by default to good choices. Not “no” to everything.
Friction only exists where risk actually exists. Not uniformly across every action.
Risk-based automation beats blanket policies. Every time.
Three Examples of Invisible Security
1. Firewalls That Don’t Block Progress
At one company, firewall requests were a nightmare. Every change required multiple security approvals. Teams waited weeks for routine changes. Engineering was frustrated. Security was drowning in tickets.
We redesigned around risk-based automation.
Internal-to-internal communication over pre-approved standard ports? Auto-approved. Minimal risk, no manual review needed.
Anything involving external networks or third parties? Human review required. These actually warranted security evaluation.
Engineering teams could make low-risk changes instantly. Security focused on changes that actually mattered. Security posture didn’t weaken, it got stronger because we could focus resources appropriately.
2. Bug Bounties That Work While You Sleep
Time-boxed penetration tests have a fundamental limitation: time. You get two weeks, maybe a month. The team finds what they can and moves on.
But some vulnerabilities are nested. Complicated. They require chaining multiple issues together in ways that take weeks to discover.
Bug bounty programs solve this by giving researchers unlimited time. They’re not watching the clock. They can spend weeks poking at complicated flows or chaining edge cases.
At another company, our bug bounty found issues that would have been hugely detrimental if discovered by attackers or customers. Issues that standard pentesting would have missed because of time constraints.
The beautiful part: The security team didn’t do anything day-to-day. The program just ran. Researchers found issues. We fixed them. Invisible security working 24/7.
3. Security Questionnaires That Don’t Kill Deals
Enterprise customer security questionnaires are a special kind of hell. Three hundred questions. Every enterprise deal requires one. Every one is urgent.
At this company, the process was a disaster. Questionnaires came via email. Responses tracked in spreadsheets. Multiple teams needed to contribute. Nobody had visibility. Sales deals sat in limbo. Response times averaged three weeks or longer.
We built a systematic process with tracking, SLAs, and accountability. We created a library of common questions with pre-approved answers. We tagged questions by specific partners so repeat customers got instant answers.
Response times dropped to under two weeks. Sales stopped complaining. Repeat customers got even faster responses.
The security review didn’t go away. It became invisible from the business’s perspective.
How to Build Invisible Security
Start with risk-based thinking. Ask: What’s the actual risk? Where does friction make sense? Where is it theater?
Automate “yes” for low-risk activities. Save human judgment for high-risk decisions. Your team’s time is valuable.
Design secure defaults. Make the secure path the easy path.
Build repeatable processes. Security questionnaires will keep coming. Firewall requests will keep coming. Build systems that handle repetitive work efficiently.
The Hard Part
Building invisible security requires significantly more upfront investment than building visible security.
It’s easy to create a policy: “all firewall changes require security approval.” Done.
It’s hard to design a risk-based automation system that intelligently routes requests, maintains approved port lists, understands network zones, and handles edge cases.
Most organizations build security reactively. An incident happens, add a control. Another incident, another control. Soon you’ve got a patchwork that slows everything down.
The best security programs are architected with intention, like that forest. Someone has to think through the whole system: How does this work together? Where is friction necessary? Where is it wasteful?
That requires experience, vision, and organizational commitment to invest in doing it right.
The Pitch
I’ve spent 20+ years building security programs that enable growth instead of blocking it. Programs where security says yes by default to good choices. Programs where teams barely notice security because the architecture just works.
If your organization needs a CISO or head of security (full-time or fractional) who thinks about these problems, let’s talk. I’m exploring new opportunities and particularly interested in organizations that want security programs as carefully designed as that engineered forest.
Because the best security looks effortless but is intentionally designed.
Want to discuss security architecture, invisible systems, or have your own examples of well-designed programs? Find me on LinkedIn or check out more writing at loravaughn.com.