Security Engineer or vCISO? Your First Hire, by Stage
A security engineer builds; a vCISO decides. Which one your startup needs first, stage by stage — and the cases where the answer isn't a vCISO at all.
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Posts tagged security
12 posts on security. Or browse the full writing index →
Posts tagged security
Secrets Management for AI Agents on Small Teams
Your agent doesn't need your production keys — its tools do. The broker pattern, per-tool scoping, and what a five-person team can skip despite vendor pitches.
A Scared Team Is Your Biggest Attack Surface
A scared employee hands over access to avoid a manager's wrath — the exact move social engineering exploits. Why psychological safety is a security control.
What Cyber Insurance Underwriters Ask AI Startups
The cyber insurance application is a security audit in disguise. What underwriters check in 2026, the AI exclusions creeping in, and when coverage is real.
Why Auto-Filled Security Questionnaires Kill AI Deals
Why auto-filling an enterprise security questionnaire backfires on an AI startup — the answers that kill deals, and the questions your SOC 2 won't cover.
Prompt Injection Defense for a 5-Person AI Startup
Prompt injection defense a five-person team can ship in a week — trust boundaries, least-privilege tools, approval gates, and what not to build yet.
What 90 Days of a Fractional Security Engagement Actually Looks Like
Most founders who book the intro call have already read three or four of my posts and arrive at the same question: "Okay, but what would the next 90 days actually look like if I hired you?" Here's the answer — week by week, with the real numbers.
An AI Just Deleted a Production Database in Nine Seconds. Hire More Engineers.
Replit's AI agent ignored a code freeze, wiped a production database in nine seconds, then confessed it violated every principle it was given. The strongest case yet for hiring MORE senior engineers in the AI boom — not fewer.
SOC 2 Is a Revenue Tool, Not a Security Tool
Every AI founder pre-Series A scopes their SOC 2 audit like a security project. Six months later they've burned their best engineer and lost the enterprise deal. Here's how to run it as a 90-day sales project — and unlock the pipeline you're already leaving on the table.
How I'd Run Security at an AI-Native Company in 2026
AI-native companies need a security model that classic appsec doesn't cover. Agents have credentials. Prompts are an attack surface. Training data leaks. The four-layer security stack I'd build, the controls I'd ship in the first 90 days, and the ones I'd defer.
vCISO Math for AI Founders: Why 5 Hours a Month Beats a Full-Time Hire
A full-time CISO costs $200–400K plus equity. A vCISO costs $2–4K a month and gives you 80% of the value at 5% of the burn — until you outgrow them. The math, the deliverables to expect, and the red flags that mean you've hired the wrong one.
Migrating 225K Users from AWS Cognito to Auth0 Without Forcing a Single Logout
How we moved 225K+ users with $400M+ in fintech assets from AWS Cognito to Auth0 without forcing a password reset, breaking MFA, or interrupting active sessions. The lazy-migration pattern, the gotchas, and what I'd do differently.