Frequently Asked Questions

Who do you typically work with?

I work with founders, executives, and senior leaders who are responsible for outcomes but don’t need — or want — a full-time CTO or CIO.

Some clients are technical. Many are not. What they have in common is that the cost of bad decisions is high enough to justify senior input.

Do you work with startups or established companies?

Both.

I’ve worked with early-stage startups, mid-sized organizations, and large enterprises, including government and regulated environments. The engagement model is flexible; the expectation of professionalism is not.

How are you different from a consultant or contractor?

Most consultants deliver reports. Most contractors deliver tasks.

I focus on decision quality.

That means:

  • identifying failure modes early
  • preventing expensive mistakes
  • intervening where judgment, not labor, is the constraint

Sometimes that includes hands-on work. Often it does not.

How do you charge?

There are three common engagement models:

  • Monthly retainer for ongoing fractional leadership (to manage cash-flow, this can also be billed bi-weekly or weekly)
  • Hourly for steady but uneven work
  • Short-term / ad-hoc engagements for acute problems

Details are discussed after an initial conversation, once scope and expectations are clear.

Do you guarantee outcomes?

No — and anyone who does is lying.

What I do guarantee is honest assessment, experienced judgment, and good-faith effort. Software, teams, and markets are complex systems. Success depends on many factors beyond any one person.

Do you work remotely?

Primarily, yes.

Occasional in-person meetings are possible when valuable, but most work is done remotely and asynchronously to respect everyone’s time.

Intermittent on-site visits and travel are acceptable – provided travel expenses and half of travel time are paid by the client. I am based in Baltimore City.

What kinds of projects are a bad fit?

Engagements tend to fail when:

  • Leadership is unwilling to hear or accept uncomfortable information
  • Authority and responsibility are badly misaligned
  • There is no intention to act on recommendations
  • The organization is looking for validation rather than clarity

If I see these conditions early, I’ll say so.

How do we start?

The first step is a short conversation to see whether there’s a mutual fit.

If it looks promising, I’ll propose a small, clearly scoped engagement. From there, we decide whether it makes sense to continue.

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