Groundwork Technology Advisors

Long-form thinking on technology leadership

Practical writing on the decisions and challenges that technology leaders at small and mid-size companies face most often.

What Does a Fractional CIO Do and When Does Your Company Need One

A fractional CIO provides part-time senior technology leadership without the cost of a full-time executive hire. Here is what the role actually involves and how to know when your company needs one.

How to Do a Technology Assessment for Your Business

A technology assessment gives your leadership team a clear, honest picture of your current technology environment. Here is what the process involves and what you should walk away with.

Why Your Engineering Team Is Underperforming and How to Fix It

When engineering delivery is slow or inconsistent, the problem is rarely the engineers. Here is how to diagnose what is actually happening and what to do about it.

When should I hire a fractional CIO or CTO?

A fractional CIO or CTO is a part-time executive who owns the technology agenda when a full-time hire is more than the role needs. The signals it is time, which seat you actually need, and how the engagement runs.

How to Prepare for a SOC 2 Audit Without Losing Six Months of Productivity

SOC 2 preparation does not have to derail your organization. Here is a practical approach to getting audit-ready without treating compliance as a full-time job.

How to Build a Technology Roadmap That Actually Gets Used

Most technology roadmaps end up in a shared drive and never get referenced again. Here is what makes the difference between a roadmap that drives decisions and one that does not.

Is Your Company Ready for AI: What to Check Before You Invest

Most companies are using AI before they are ready for it. Here is a practical framework for understanding where your organization actually stands and what needs to be in place before AI investment delivers real returns.

Most AI projects do not fail for technical reasons

A large share of AI and data spending is being written off, and the reason is almost never the technology. Why the failures are leadership and organizational, and what a seasoned technology leader changes.

Why systems go down, and what keeps them up

Most outages are not exotic failures. They are ordinary, preventable process problems. The engineering practices and business-continuity discipline that keep systems up.

Why your technology spend is a black box, and whether you are overpaying

Large technology invoices that rise every year, with no clear answer on value. Most of what is hiding in there is technical debt, and how to get the black box open.

When legacy systems hold the business back

The technology that got you here starts working against you at scale. Why big replacement programs fail and what incremental modernization that works looks like.