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Tech leadership in the AI era

The Weekly Newsletter for Technology's Next C-Suite Role

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This Week's Reads

Pulled from Reddit, Hacker News, YouTube, podcasts, and a few other places worth reading.

AI & ML Today

What Claude Code Actually Chooses — Tool Preferences Across 2,430 Repos

Research benchmarking real tool selection patterns. Claude prefers to build over buy in 12 of 20 categories.

Engineering 5h ago

Show HN: I replaced our entire CI/CD with Claude Code

A startup CTO documents replacing Jenkins, GitHub Actions, and ArgoCD with an AI-driven deployment pipeline.

891 267
Observability 3d ago

Datadog's enterprise pricing is driving teams to Grafana

Engineering leaders share migration stories and TCO comparisons after moving to open-source alternatives.

2.4K 384
Leadership 2d ago

The Death of the CTO Title — What Comes Next

Panel with former CTOs of Stripe, Shopify, and Uber on how the role is fragmenting into CAIO, CTPO, and VP Eng.

45K 1200
Infrastructure 1d ago

We moved from Kubernetes to bare metal and saved $2M/year

Detailed post-mortem from a Series C company covering toil, latency, and the hidden costs of k8s at mid-scale.

3.1K 512
Engineering 4d ago

Lenny's Podcast: Why platform teams fail

Common anti-patterns in internal platform teams and why the best ones operate like product teams.

28K
Org Design 6d ago

Inside Google's AI-First Reorg

How AI-first reorgs unfold — what gets consolidated, what gets cut, and what it means for senior eng leadership.

89K 2300
AI & ML 2d ago

Ask HN: How are you handling AI governance at your company?

Real governance frameworks from practitioners covering model risk, shadow AI, and board-level reporting.

456 189
Enterprise 5d ago

The $100M ERP migration that almost killed our PE portfolio company

Lessons from a failed SAP-to-cloud migration at a PE-backed portfolio company. What went wrong and the recovery.

1.8K 290
AI & ML 3d ago

a16z: The AI agent stack for enterprises

Breakdown of the emerging enterprise AI agent stack — orchestration, memory, guardrails, and deployment.

41K
Hiring 4d ago

Why we stopped hiring senior engineers and started hiring AI-augmented juniors

Controversial take on how AI pair programming is reshaping the seniority ladder and team composition.

1.2K 743
Leadership 1d ago

Board-level AI metrics that actually matter

Moving beyond "number of AI projects" to metrics that boards actually care about: revenue impact, risk, and ROI.

32K 890

Real conversations with the people running tech at scale.

The CTAIO Podcast — Thomas Prommer in recording studio

CTAIO Jobs

Senior tech leadership roles from 200+ niche headhunters and executive search firms.

via LinkedIn

Chief AI Officer

Fortune 500 Retail

New York $450-550K
via Heidrick & Struggles

CTO/CIO (combined role)

PE-backed SaaS

Remote $380-480K
via Spencer Stuart

VP AI & Data Strategy

Global Bank

London £280-350K
Thomas Prommer

Thomas Prommer

Technology executive, founder, and Ironman. 30+ years in tech. Led 1,000+ engineers at Adidas, Sweetgreen, Huge. Ships code daily. Chases finish lines.