Technology Leadership
16 posts on this topic — practical guidance from Shawn Livermore on fractional CTO, AI, and technology leadership.
Microsoft Just Bet $2.5 Billion That AI Implementation Is Harder Than AI Technology
Microsoft launched the Frontier Company on July 2, committing $2.5 billion and 6,000 engineers to fix enterprise AI pilots that fail. The announcement names the real problem — and reveals which companies get the answer and which don't.
Read post →What a Fractional CTO Actually Owns in the AI Era
AI changed what developers can produce. It didn't change what a technology executive is accountable for. Here is what the fractional CTO role actually covers when AI is handling more of the coding.
Read post →The Decisions a Fractional CTO Has to Own (and the Ones That Aren't Theirs to Make)
Decision authority in a fractional CTO engagement is frequently misunderstood. Some decisions require the fractional CTO to hold firm even when that creates friction. Others shouldn't be made by the fractional CTO at all — and confusing the two is what derails engagements.
Read post →What Companies Get Wrong in the First 30 Days of a Fractional CTO Engagement
Most fractional CTO engagements that underperform weren't set up to succeed. The conditions that determine whether a fractional CTO can do their job are established by the company before the real work begins — and most companies get three of them wrong.
Read post →What a Fractional CTO Actually Does on Day One
Most descriptions of a fractional CTO engagement are abstract. Here is what the first engagement actually looks like: the first conversations, the real deliverables, and where the work concentrates in the first 90 days.
Read post →Fractional CTO as a Permanent Operating Model, Not a Stopgap
Most companies treat fractional CTO as a bridge to a full-time hire. For many mid-market organizations, the fractional model is the permanently correct structure — not a placeholder for something better.
Read post →Why the AI Era Is Creating More Demand for Fractional CTOs, Not Less
AI tools are making code easier to write. That hasn't reduced the need for technology leadership, it has intensified it. Why fractional CTO demand is rising now.
Read post →What a Fractional CTO Delivers in the First 90 Days
The first 90 days of a fractional CTO engagement should produce decisions, not a binder of audits. What good looks like at 30, 60, and 90 days, plus the red flags.
Read post →When a Fractional CTO Is the Right Call — and When You Actually Need Something Else
The choice isn't always fractional vs. full-time. How to tell whether you need a fractional CTO, a tech advisor, or a consulting firm, and what a misstep costs.
Read post →Which Claude Model Your Business Actually Needs
Anthropic released 29 Claude models and tools in the first five months of 2026. The question is not which is most capable, but which fits the work you are doing.
Read post →When to Hire a Fractional CTO: 5 Signals That Tell You It's Time
Not every company needs a full-time CTO. Here are the five clearest signals that fractional CTO expertise is what your business actually needs right now.
Read post →What Does a Fractional CTO Actually Do? Day One Through Month Six
A detailed look at what a fractional CTO does in practice — from the first-week assessment through steady-state leadership, board reporting, and hiring decisions.
Read post →What Is a Fractional CTO? (And When Your Business Actually Needs One)
A fractional CTO brings executive technology leadership part-time. Learn what the role covers, how engagements work, and the four scenarios that signal you need one.
Read post →Legacy System Modernization: Rebuild, Wrap, or Replace?
Rebuild, wrap, or replace? Here is the framework technology leaders use to choose a legacy system modernization approach that minimizes risk and disruption.
Read post →Fractional CTO vs. Technology Consultant: The Difference That Actually Matters
A consultant delivers a report and exits. A fractional CTO owns your technology function. Here is how to tell the difference and know which one you need.
Read post →How to Build a Technology Roadmap: A Framework from a Fractional CTO
A technology roadmap is not a Gantt chart or a feature list. Here is a practical framework for building one that earns executive buy-in and actually gets executed.
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