TL;DR
We went from no security practices to passing enterprise security reviews in 18 months. It wasn't about becoming security experts. It was about building habits: automated scanning, regular reviews, and treating security as part of the development process rather than an afterthought. Here's our step-by-step journey.
When we started, security was that thing we'd "figure out later." Eighteen months later, we passed our first enterprise security questionnaire and won a deal we would have lost otherwise. This is how we got there.
The Journey Timeline
Lost a potential customer because we couldn't answer their security questionnaire. Realized "we'll add security later" had caught up with us. Decided to take it seriously. ::
Moved API keys to environment variables. Enabled 2FA on all team accounts. Set up HTTPS everywhere. Added basic auth to admin routes. Quick wins that fixed obvious holes.
Added npm audit to CI/CD. Set up Dependabot for automated updates. Created a security checklist for code reviews. Made security part of our definition of done.
Implemented rate limiting. Set up proper logging and monitoring. Added WAF rules through Cloudflare. Created incident response documentation.
Started documenting security policies. Implemented data encryption at rest. Set up access controls and audit trails. Prepared for security questionnaires.
Hired a penetration tester. Fixed the issues they found (mostly minor). Used their report to validate our progress and identify gaps.
Passed our first enterprise security review. Won the deal. Security became a competitive advantage instead of a weakness.
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What Actually Worked
Looking back, a few things made the biggest difference:
"The game changer wasn't any single tool or practice. It was making security a habit rather than a project. Once it became part of how we build, it stopped feeling like extra work."
Automation Over Willpower
Every security check we could automate, we automated. Humans forget. CI/CD pipelines don't. npm audit, secret scanning, dependency updates - if a tool could do it, we let the tool do it.
Small Consistent Improvements
We didn't try to fix everything at once. We picked one thing each sprint. Rate limiting one sprint. Input validation the next. Compounding improvements added up faster than a big security overhaul would have.
Documentation as You Go
Every time we implemented something, we documented it. When the security questionnaire came, we had answers ready. The documentation also helped new team members understand our security practices.
- Start with the basics - 2FA, HTTPS, env variables - before anything fancy
- Automate everything you can - humans are unreliable, pipelines aren't
- Make security part of the process, not a separate project
- Document as you go - you'll need it for compliance later
- Incremental progress beats big security initiatives
- A pen test validates your work and finds what you missed
The Investment
People ask about the cost. Here's what we actually spent:
- Tools: ~$200/month (monitoring, secret scanning, etc.)
- Time: ~2-4 hours/week of developer time
- Pen Test: $5,000 one-time
- Training: Internal knowledge sharing (free)
Compare that to the enterprise deal we won: $120,000/year. The ROI was obvious in hindsight, but it took losing a deal to see it.
How do you prioritize what to fix first?
Start with authentication and access control - they prevent the worst outcomes. Then move to data protection, then infrastructure hardening. Fix what's exploitable before what's theoretical.
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When should a startup get a pen test?
After you've fixed the obvious issues but before major enterprise sales or funding rounds. Don't pay someone to tell you your API keys are exposed - fix that first. A pen test validates your work and finds what you missed.
Can you do this without a dedicated security person?
Yes. We didn't have one until much later. The key is making security everyone's responsibility through process and automation. You don't need an expert to follow a checklist.
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