The newsletter for technology's next C-suite role
CTAIO — Where CTO Meets CIO Meets AI
Weekly intelligence from a practitioner-executive who ships production code, manages $200M IT budgets, and advises PE firms on billion-dollar technology bets.
Free every Monday. Unsubscribe anytime.
Who this is for
CTOs Building AI-native engineering organizations
CIOs Enterprise infrastructure, vendors, $100M+ IT budgets
Chief AI Officers Enterprise AI strategy & governance
VP Engineering Scaling teams 10 to 1,000 engineers
PE/VC Partners Technology bets with conviction
The practitioner-executive edge
Most newsletters come from one side. This one comes from both.
I still ship code
- Python & TypeScript daily
- Tests every AI coding tool hands-on
- Builds and operates production platforms
- 30+ years of continuous engineering
I've run the org
- CTO/CIO at Adidas (500+ engineers)
- CTO Sweetgreen (rapid growth)
- $200M IT budget responsibility
- President, Huge/IPG (digital agency)
What you'll get every Monday
◆
Enterprise AI Intelligence
Vendor evaluations, budget trends, and the $500/hr insights I share with Fortune 500 boards — delivered free to your inbox.
▶
CTO + CIO Operations
Platform consolidation, infrastructure modernization, org design — the operational playbook from running both sides of the house.
▲
The Practitioner's Edge
Real tool reviews, real code, real experiments. From someone who still ships production code daily, not just talks about it.
Topics I cover
- AI coding tools (Cursor, Claude Code, Copilot)
- Observability (Datadog, New Relic, Grafana)
- GenAI adoption (ChatGPT Enterprise, Anthropic, Copilot)
- Platform consolidation (Adobe vs Salesforce, ServiceNow)
- ERP modernization (SAP S/4HANA, Oracle Cloud)
- IAM (Okta, Auth0)
- Cloud strategy (AWS, Azure, GCP)
- Engineering org scaling (0 to 1,000 engineers)
- Tech due diligence for PE/VC
- Build vs buy at enterprise scale
