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Field notes on getting AI pilots into production, leading engineering teams, and the decisions that separate a demo from a durable system.

  1. Apr 16, 2026

    Anthropic Won't Patch the MCP Vulnerability in 150 Million Downloads. Now What?

    Anthropic declined to patch a critical RCE in its official MCP SDK across 150M+ downloads. Here's the CTO playbook to audit your deployments this week.

    • ai-strategy
    • security
    • implementation
  2. Apr 9, 2026

    43% of Your MCP Servers Have a Command-Injection Vulnerability. Now What?

    43% of MCP servers have command-injection flaws. Three real breaches prove the risk. Here's the OWASP framework to audit your MCP deployments now.

    • ai-strategy
    • implementation
    • security
  3. Apr 2, 2026

    Stop Treating AI as an IT Project

    80% of AI projects fail - and the biggest predictor isn't technology. Learn why treating AI as business transformation instead of an IT project changes everything.

    • ai-strategy
    • business-transformation
    • executive-leadership
  4. Mar 26, 2026

    5 Red Flags That Kill Deals in Technical Due Diligence

    A fractional CTO reveals the 5 technology red flags that kill M&A deal valuations - and how to fix them before a buyer ever looks.

    • m&a
    • technical-leadership
    • due-diligence
  5. Mar 19, 2026

    The First Department to Automate Is Never the One You Think

    Most CEOs automate customer service first. That's usually wrong. Here's the scoring framework for picking the department with the fastest ROI.

    • ai-strategy
    • business-transformation
    • automation
  6. Mar 12, 2026

    AI-Buyout Your Own Company Before Someone Else Does

    PE firms are spending billions to buy companies and automate them with AI. Here's how to disrupt your own operations before someone else does it for you.

    • ai-strategy
    • business-transformation
    • private-equity
  7. Mar 5, 2026

    The Vendor Demo Is Lying to You

    Every vendor demo looks amazing. Then you sign the contract. A fractional CTO's framework for evaluating enterprise software beyond the sales pitch.

    • strategy
    • leadership
  8. Feb 27, 2026

    When everyone can do everything, nobody knows their job

    AI is making everyone a generalist. That sounds great - until nobody owns anything, accountability vanishes, and your org chart becomes fiction.

    • leadership
    • organizational-design
    • ai-strategy
  9. Feb 20, 2026

    The HIPAA update nobody's ready for

    The HIPAA Security Rule update makes encryption, MFA, and network segmentation mandatory. Here's what healthcare CEOs must do before the deadline.

    • healthcare
    • cybersecurity
    • compliance
  10. Feb 12, 2026

    How to Measure AI ROI That Actually Matters

    77% of organizations can't prove AI delivers value. Learn the Three-Pillar Framework that separates the 6% of high performers from everyone else.

    • ai-strategy
    • roi
    • leadership
  11. Feb 9, 2026

    The 15-Minute Spec That Saves 15 Hours

    Learn the 5-question spec that transforms AI coding from frustrating to productive. Template included. Takes 15 minutes, saves hours.

    • ai
    • engineering
    • productivity
  12. Feb 3, 2026

    Working With AI Means Doing More Work

    Companies getting the best AI results are doing more work, not less. Learn why specifications, context, and structure unlock AI productivity.

    • ai
    • engineering-leadership
    • productivity
  13. Jan 26, 2026

    Execution Is Cheap Now - Why Your Approval Process Is Killing Innovation

    Developers complete 21% more tasks with AI - but companies see no gains. The bottleneck has shifted from execution to approvals. Here's how to fix it.

    • engineering-productivity
    • ai-tools
    • organizational-design
  14. Jan 20, 2026

    Why Your Best Engineers Keep Leaving (And It's Not About the Money)

    69% of engineers prioritize career growth over salary. Learn the three factors - beyond compensation - that actually keep your best technical talent from leaving.

    • leadership
    • engineering
    • retention
  15. Jan 10, 2026

    Why Your Cloud Bill Keeps Surprising You (And How to Fix It)

    78% of companies don't know their cloud costs changed until the bill arrives. The fix isn't tools - it's visibility and accountability.

    • cloud
    • finops
    • cost-optimization
  16. Dec 20, 2025

    Why Your AI Needs a Job Description (And You Probably Didn't Write One)

    Most AI projects fail - not because the technology is wrong, but because the specifications are missing. Learn how to write AI job descriptions that actually work.

    • ai
    • strategy
    • leadership
  17. Dec 13, 2025

    Why 73% of GenAI Pilots Fail to Reach Production

    73-95% of GenAI pilots never reach production. Learn the 5 failure patterns from RAND and MIT research - and what the successful 27% do differently.

    • ai
    • strategy
    • leadership
  18. Nov 20, 2025

    AI Doesn't Care If It's Wrong - That's Why You Need Humans in the Loop

    Why the most successful AI implementations keep humans accountable - and why over-automation leads to billion-dollar failures

    • ai
    • leadership
    • human-ai-collaboration
  19. Nov 5, 2025

    The Art of Technical Prioritization in Growth-Stage Companies

    A practical framework for deciding what to build when everything feels urgent

    • strategy
    • prioritization
    • leadership
  20. Nov 4, 2025

    Aligning Engineering Teams with Business Goals: A Framework

    How to translate between technical teams and business goals to drive measurable impact

    • leadership
    • team-management
    • strategy
  21. Nov 3, 2025

    Breaking Down Data Silos: A Practical Architecture Guide

    How to architect unified data platforms that unlock trapped data and scale globally

    • data-architecture
    • data-strategy
    • platforms
  22. Nov 2, 2025

    From AI Pilot to Production: A Framework for Getting Unstuck

    Why most companies get stuck in the AI pilot phase - and the practical framework for shipping to production

    • ai
    • mlops
    • implementation
  23. Nov 1, 2025

    Welcome to My Blog

    Introducing a new resource for technical leadership and AI implementation insights

    • announcement
  24. Nov 1, 2025

    Why Most Fractional CTOs Fail (And What Makes the Difference)

    The three capabilities that separate effective fractional CTOs from the rest - and why most fall short

    • fractional-cto
    • leadership
    • strategy