Red Dog Advisors

Fractional Technology Leader

Senior technology leadership for companies who need the judgment of a CTO without the full-time costs.

You’re in the right place if…

  • Your systems decisions are being made without a cohesive strategy or each function simply does they’re own thing
  • You have growing IT spend and no one knows if the spend will improve operations and lead to higher profits
  • Your technology stack has grown but hasn’t been modernized; and much isn’t integrated
  • A major initiative (e.g. ERP selection, AI strategy) is being considered and the internal team has limited relevant experience
  • Your last technology hire didn’t work out, and you’re not sure what to look for next
  • You’re between CTOs, or you’re not yet at the size where a full-time one makes sense

How It Works

TIme to Ask, Listen, and Understand

I meet you, your leadership team, and your functional leaders to review your systems, key processes, constraints, budgets, and spend. I sit in on the meetings where technology decisions are being made. In the first 3-4 weeks, I’ll have a good sense of where you are and what you need. You then get a written assessment on what’s working, what’s at risk, and what changes I’d recommend.

We Align on a Roadmap and Begin to Execute

We’ll align on a roadmap to resolve they key needs of your business. Most engagements run 1-2 days a week depending on the size and complexity of the need. My work is a combination of onsite and remote work. I attend relevant leadership meetings, own the technology roadmap, and oversee projects that matter.

We Build Toward Your Independence

Fractional leadership isn’t permanent. Most times a part of my role is helping hire or develop whoever will take over — an internal lead, a first CTO hire, or a smaller ongoing advisory role with me.

What you get

  • A technology roadmap tied to your business strategy
  • Vendor and contract management — including renewal negotiations (most clients find that I save them meaningful money)
  • A named owner for every active technology project
  • Leadership-team representation: someone who can translate between business needs and systems to support them
  • Hiring support when you’re ready to bring the role in-house

Engagement and investment

Most fractional engagements run 3–12 months at 1–2 days per week, depending on the size and complexity of the need. Shorter interim coverage—filling a gap between CTOs—is also possible.

Why me

Over 25 years leading multiple functions and technology initiatives in various sized organizations, including leadership roles at Fidelity Investments, Paycor, Velosio, and Allmerica Financial. I’ve been on both sides: running technology inside a company, and advising from outside. I know which one your situation actually calls for, and I’ll tell you if it isn’t me.

Proof

A $350M specialty manufacturer and distributor needed the right leadership to assess their entire tech stack of over 80 systems. Over just a few months we redesigned their future tech stack to significantly streamline operations, reduce systems costs, improve the employee user experience, and prepare the company for leveraging modern features and AI.

Note Sure Yet?

Read: When a mid-market company needs a CTO — and when it doesn’t.

Ready to get started?

Let’s talk about whether fractional leadership fits your situation.

Let’s Talk