Alex van Rossum

I find the things that slow organizations down.

Fractional CTO, systems architect, AI strategist. I diagnose what's broken, architect the fix, and guide teams through execution — whether the problem is infrastructure, governance, vendor complexity, or all three at once.

Most people work in either infrastructure or governance. I work in the space between them, where the real failures happen.

Not Sure Where to Start?

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Do You Need a CTO?

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Should You Move Off WordPress?

Live performance audit + migration readiness assessment.

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AI Readiness Scorecard

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Case Studies

Real problems. Real constraints. Real outcomes.

9 servers · 150+ K8s deployments

managed by a governed AI agent, daily production use for 8 months

Sysadmin Claude — Autonomous Infrastructure Agent

An autonomous infrastructure operations agent built on Claude Code. It SSHes into production servers, runs kubectl against a live EKS cluster, executes fleet-wide operations, and gets faster every session through self-maintaining institutional knowledge. Governed by layered authority — not trust.

Claude Code Infrastructure Autonomous Agent Governance
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260 deployments

migrated solo, zero downtime

Emergency Kubernetes Migration

The control plane died, SSH keys were lost, TLS certs expiring in weeks. I built a new EKS cluster from scratch and migrated everything — alone.

Kubernetes AWS Crisis Response
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32,000+

metadata changes migrated

Salesforce Architecture & Migration

Three years of stalled progress across five integrated systems. Learned the platform from zero, executed the migration, and stayed to fix the architecture.

Salesforce Architecture Governance
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3 hrs → <1 hr

daily PM overhead

AI Sprint Management System

A human-in-the-loop AI agent that orchestrates sprint workflows, translates between technical and client language, and maintains context across sessions.

AI Systems Design Claude
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40%

cost reduction

AI-Assisted AWS Infrastructure Governance

Years of AWS drift. No documentation. No audit trail. An AI agent broke the information asymmetry stalemate — enumerating every service and producing the governance documentation that makes future drift measurable.

AWS Governance Claude Code
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What I Do

Fractional CTO work across three domains.

Systems Architecture

Infrastructure design, Kubernetes orchestration, cloud migrations, CI/CD pipelines. I build the systems that other systems run on — for organizations that have outgrown their initial setup but don't have a dedicated infrastructure team.

AI Integration

Operational AI — not chatbots. Human-in-the-loop agents, workflow automation, prompt engineering, and the safety frameworks to deploy them responsibly. For teams that want AI doing real work, not generating summaries.

Technical Strategy

Translating business problems into architecture decisions. Evaluating build vs. buy, designing for constraints, and making the call when there is no playbook. For leaders who need a technical partner, not a vendor.

How I Think

Systems thinking. Pragmatism. Deliberate constraints.

Fix the system, not the symptom

When I look at a problem, I see how the pieces connect and where the real failure point is. The goal is an architecture where this problem doesn't come back.

Ship over perfect

The best architecture accounts for the constraints you actually have — not the ones you wish you had. I'd rather deliver something that works than design something perfect.

AI with guardrails

AI agents should be designed with deliberate constraints. The systems I build keep humans in the loop — not because the technology can't do more, but because operational safety requires it.

Latest Thinking

All posts →

Every Management Failure Is a Retrieval Failure

April 1, 2026

Latency Kills Curiosity

March 30, 2026

Also

I build macOS tools.

Productivity software built for speed, focus, and getting out of the way.

Actions

Menu-bar command launcher

Coming Soon

Simple Markdown Editor

Three-pane markdown editor

Open Source

Panoptisana

Task-forward Asana interface

Open Source

Ready to talk?

No pitch deck. No 30-minute discovery call. Tell me the situation, and I'll tell you whether I can help.