Skip to content

Insights

Field notes on AI, security, and IT operations

What changed, and what to do about it, for leadership teams running technology without a full-time CTO.

Get the weekly brief

How to Build a 12-Month IT Roadmap and Budget Your CFO Can Actually Read

2026-10-30

How to Manage Your Managed Service Provider: An MSP Oversight Checklist for Mid-Market Owners and Operators

2026-10-27

When to Move a Process Off Spreadsheets: A Decision Guide for Mid-Market Owners and Operators

2026-10-25

ERP Replacement Without the Wreckage: A Decision and Rollout Guide for Mid-Market Owners and Operators

2026-10-22

How to Cut Cloud Waste: A FinOps Playbook for Mid-Market Owners and Operators

2026-10-20

What a Fractional CTO Should Deliver in the First 90 Days: A Checklist for Mid-Market Owners and Operators

2026-10-19

Keep, Move, Replace, or Rebuild? A Legacy System Modernization Decision Guide for Mid-Market Owners and Operators

2026-10-16

Fractional CTO, Full-Time CTO, or a Better MSP? A Decision Guide for Mid-Market Owners and Operators

2026-10-13

Google's Gemini Agent Picks the AI Model for Each Task — Set Spend Caps and Approval Rules Before It Reaches Your Workspace

2026-10-10

Meta Just Hired for Enterprise AI — Run Build-vs-Buy Before You Rewrite the Stack

2026-09-29

Claude Opus 5.5 Just Cut Agentic Coding Costs — Your Workflow Still Decides the Bill

2026-09-28

DeepSeek Just Hit a $1B Run Rate — Your AI Bill Is Now a Strategy Decision

2026-09-27

Not sure which seat you need? That's what the first call is for.

Book a 20-min call