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New CTO Starter Pack
Curated collection of essential insights and frameworks for CTOs in their first 90 days, organized in recommended reading order.
•6 min read•
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insights
AI by Default Means Platform by Necessity: The New CTO Stack (GPUs, Vectors, and Governance)
Teams are transitioning from “trying AI” to running AI as a first-class production workload: building shared AI platforms, optimizing GPU utilization, embedding vector search into core data systems,...
•3 min read•
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guides
CTO Rating Framework Guide: A CTO skills assessment you can turn into a 90-day plan
CTO Rating Framework Guide: CTO skills assessment for Series A and early Series B
•12 min read•
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insights
How I run a 1:1 with engineers that actually works
In a 50 person engineering org, a CTO with 8 direct reports can spend 4 hours a week in 1:1s. That is 200 hours a year per report if you meet weekly for 30 minutes.
•13 min read•
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insights
5 Things I’d Stop Doing Immediately as a New CTO
In your first 90 days, it’s easy to burn weeks on work that feels responsible but quietly slows the company down.
•12 min read•
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insights
Ward Cunningham’s Technical Debt: The Quadrant Model CTOs Can Actually Run
Ward Cunningham technical debt and the quadrant model
•11 min read•
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insights
TOGAF and ArchiMate for CTOs: Use Them as Decision Tools, Not Paperwork
TOGAF and ArchiMate for CTOs: Use Them as Decision Tools, Not Paperwork
•12 min read•
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insights
Tech Stock Shakeouts: What CTOs Should Do When Markets Punish Software Multiples
Key Takeaways: Treat a tech-led selloff as a budget and risk reset, not a morale event. Reprice projects in weeks, not quarters.
•9 min read•
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insights
What a CIO Actually Does (and How a CTO Can Work With Them Without Losing a Quarter)
Most CTOs I talk to have a fuzzy mental model of the CIO. Not because they're careless—because the CIO job shape-shifts depending on the company.
•5 min read•
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insights
The CTO Role Is Converging with AI + Product Leadership (and Talent Volatility Is Now a Strategy Risk)
The CTO role is being redefined around AI: companies are hiring CTOs with generative AI pedigrees, expanding CTO scope into product and business operations, and contending with intense AI talent churn that can reshape execution risk and long-term strategy.
•3 min read•
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insights
AI Is Now a Regulated Operational Risk Surface (Not Just a Product Feature)
AI is rapidly becoming a regulated operational surface: CTOs are being asked to govern model behavior, third-party dependencies, and consumer outcomes with the same rigor as security and financial ...
•3 min read•
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insights
The Dual-Mandate CTO: Executive Scrutiny Meets AI Systems Governance
CTO leadership is entering a “dual mandate” era: markets and boards are scrutinizing CTO moves like executive events, while the technical agenda is shifting toward AI system design, privacy control...
•3 min read•
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insights
Agentic AI Is Entering the Pager Rotation: Autonomous SRE Moves from Observability to Control Loops
Agentic AI is moving from copilots to production control loops: vendors are pitching autonomous SRE and AI-native observability, investors are backing closed-loop remediation platforms, and boards are hiring AI-focused CTOs to operationalize these capabilities.
•3 min read•
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