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fractional CTO

  • Agile and Process Optimization
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  • Mentorship, Growth & Human Skills
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  • Oct 6, 2026
    AI, Automation & the New Engineering Landscape, Managing Growth Challenges, Metrics and Measurement

    Orchestration Is Becoming a Feature. Governance Isn’t.

    Last week, I wrote about code getting cheaper to generate while the work of verifying it remains. The releases from September 29…

  • Sep 29, 2026
    AI, Automation & the New Engineering Landscape

    Generation Got Cheaper Again. Verification Didn’t.

    An agent can finish a change in minutes and leave it waiting for review for two days. The generation was fast. The…

  • Sep 20, 2026
    AI, Automation & the New Engineering Landscape, Scaling Systems and Teams

    Your Engineering Process Should Outlive Your Model Vendor

    The past couple of weeks have stirred things up among the major players in frontier AI, and a few who would like…

  • Aug 31, 2026
    AI, Automation & the New Engineering Landscape, Product and Customer Feedback, Scaling MVPs and Architectures

    O’Side Systems Product and Business Roadmap Update

    A redesign, a retirement, and what comes next I haven’t posted in a while, but I have been busy. Now seems like…

  • Feb 16, 2026
    Scaling Systems and Teams

    The Hidden Cost of Hero Culture in Engineering

    Why high-performing teams need systems, not saviors. Early in my career, I worked with engineers I can only describe as forces of…

  • Feb 9, 2026
    Leadership & Culture in Engineering

    How to Build Culture Across Oceans

    Lessons from Global Engineering Teams Building culture in a colocated team is hard enough. Doing it across continents, time zones, and cultural…

  • Jan 26, 2026
    Scaling Systems and Teams

    Rethinking Customer Support Organizations

    Why support teams may be the most underutilized source of quality engineering and software talent. I started my career in tech in…

  • Jan 19, 2026
    Transitioning from Corporate to Entrepreneurial Leadership

    Building a Business Like an Engineering System

    How modularity, feedback loops, and observability apply to entrepreneurship. When I first started O’Side Systems, I assumed my biggest challenge would be…

  • Jan 12, 2026
    Mentorship, Growth & Human Skills

    Building a Mentorship Culture Without Formal Programs

    Practical steps for managers who want to start small. Many teams think mentorship requires a formal program, dedicated resources, and a significant…

  • Jan 5, 2026
    AI, Automation & the New Engineering Landscape

    The Future CTO Is Half Coach, Half Curator

    How AI shifts the technical leadership role from problem-solver to pattern recognizer. AI is changing the shape of technical work. Tasks that…

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