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I write for three audiences: founders trying to unlock enterprise pipeline, engineering leaders scaling AI-native teams, and senior engineers building production systems. Pick the path that fits — or read all three. The full archive of 39 posts lives at /blog →
If you're a founder
Your enterprise pipeline is stalled at the security review. These three posts are the playbook for unblocking it without burning your engineering team.
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.
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.
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.
If you run engineering
Operational throughput, team-level AI adoption, and the migrations that pay for the next round of headcount.
Most engineers using Claude Code see a 10–15% speedup. The teams seeing 40–55% aren't typing faster — they're sequencing work differently. The four modes I use AI in, what to never delegate, and how to get a skeptical team across the line.
Migrating an AI-first product from GCP to Azure cut $350K from infrastructure spend over six months. The negotiation that mattered more than the architecture, the $50K we accidentally cost ourselves back, and the four migrations I'd refuse to do today.
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.
If you write code
Real-world technical writeups from production systems, plus the workflow patterns I've adopted with AI tooling since 2023.
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.
Most engineers using Claude Code see a 10–15% speedup. The teams seeing 40–55% aren't typing faster — they're sequencing work differently. The four modes I use AI in, what to never delegate, and how to get a skeptical team across the line.
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.
Working on something ambitious?
If anything in these posts maps to a problem you're sitting on right now — staff engineering hire, fractional security leadership, AI product delivery, multi-cloud modernization — let's talk.
Direct: jared@sublimecoding.com
LinkedIn: @jared-smith