Chris Steele

Fractional CTO · Freight & Logistics Technology

The CTO you want when the stakes are real.

Get in touch

01 — Premise

I've spent a lot of time in freight and logistics, including four years as CTO of a large brokerage that was nearing $1B in revenue — through the boom, and through the hard contraction we're all still working through. I now work with executive teams that need senior technology leadership without the cost or commitment of a full-time hire.

The companies making the calls that actually matter in this market — TMS replacements, post-acquisition integrations, doing more with less in a hard market — deserve advisors who've actually run this stuff, not just consulted on it. That's the gap I'm here to fill.

02 — Services

Advisory Retainer

Senior technology judgment on call. For founders, CEOs, boards, and executive teams who need an experienced CTO available for the decisions that matter — without embedding someone in day-to-day operations.

For you if: You have someone running technology day-to-day, but want a seasoned advisor for the decisions where being wrong is expensive.
Typical duration: Three months minimum, often ongoing.

Fractional CTO

A CTO embedded in your business. For companies that need a CTO actively running the technology function — owning strategy, leading the team, accountable for outcomes — but at part-time hours rather than a full-time hire.

For you if: You need a CTO right now, the role demands seniority, and a full-time hire isn't the right answer yet.
Typical duration: Six to twelve months.

M&A Technology Advisory

Hands-on help for freight and logistics companies pursuing acquisitions or preparing for integration. Pre-acquisition due diligence and post-acquisition integration are different engagements; both are work I've led directly.

For you if: You're evaluating a target, integrating a recent acquisition, or trying to land the technology synergies your deal thesis depends on.
Typical duration: Two to six weeks for diligence; three to nine months for integration.

TMS & Platform Advisory

Selection, replacement, and integration advisory across freight technology platforms. I've worked directly with most of the major TMS systems in the brokerage and 3PL space, plus the partner ecosystem around them.

For you if: You're choosing, replacing, or integrating a TMS, and the wrong call has years of operational consequences.
Typical duration: Four to twelve weeks, depending on scope.

Project Engagements

Defined-scope, defined-outcome work outside the categories above. Common shapes include technology assessments, architecture reviews, build-vs-buy analyses, and turnaround planning.

For you if: You've got a specific problem you need solved, and you want someone senior who'll actually own it with you — not just hand you a deck and disappear.
Typical duration: Four to twelve weeks, depending on scope.

03 — About

My background is 25 years in technology, with the last several years running tech for a nationwide brokerage with a large agent network. Across that career I've worn most of the seats — programmer, architect, business unit leader, COO, CTO — and the work that's been most valuable to the companies I've worked with usually lived at the intersection of those seats rather than in any one of them.

I'm a builder at heart, and I'm starting this practice because I want to spend more of my time on the technology decisions that change a business's trajectory and less on the operational firefighting that comes with running a function in-house. Working alongside companies facing real problems is the best way I know to keep that work grounded.

I'm based in Naperville, IL — about ten minutes from Bolingbrook, one of the densest freight hubs in the country.

04 — How I Work

Engagements run on a small set of principles that probably matter more than the formal structure of any given engagement. If that's useful to read about:

How I work