The leadership gap in carrier technology
Walk into most mid-sized carriers and ask who is in charge of technology. You will usually get one of three answers. The owner points at himself, because he signs every software contract. The controller says she handles it, because the TMS, accounting, and fuel card vendors all send her invoices. Or someone points at the IT person down the hall, who is buried in password resets, printer jams, and a new laptop for the dispatcher who started Monday.
None of those people is wrong, and none of them is doing the job of a Chief Information Officer. That job is not fixing computers. It is deciding which systems the business should run, how they fit together, what they should cost, what risks they create, and how they help the company move more freight with the same people. In a carrier, that means connecting the TMS, ELD, EDI, imaging, accounting, fuel, and safety systems into something that works from order entry to settlement.
Large carriers hire a full-time CIO for that. Smaller and mid-sized operations usually cannot justify a full-time executive salary, so the work either falls through the cracks or gets done in pieces by people who have other full-time jobs. A fractional CIO fills that gap: a seasoned technology leader who works with you part time, every month, and owns the outcome.
Signs you have outgrown ad hoc IT
You do not need a CIO because a consultant says so. You need one when technology problems start costing you freight, cash, or people. Look for these signs:
- Every system is an island. Dispatch re-keys loads from emails into the TMS. Billing re-keys charges into accounting. Payroll re-keys settlement adjustments into a spreadsheet. Each hand-off is a chance for an error.
- Vendors set your priorities. Your roadmap is whatever the TMS vendor's sales rep pitched last quarter, and nobody has compared it to what the business actually needs.
- Projects stall. The ELD integration has been "almost done" for a year. The new imaging system went live but half the terminals still scan to a shared folder.
- Reports do not match. Operations, finance, and sales each have their own revenue per mile, and the numbers disagree.
- You cannot answer basic risk questions. When was the last full restore test? Who has admin access to the TMS? What happens if your one IT person quits?
- Technology spend is a mystery. Subscriptions, licenses, telecom, and support contracts have grown one invoice at a time, and nobody has a full list.
- Growth is coming. A new terminal, a brokerage division, an acquisition, or a large shipper with EDI requirements is on the horizon, and the current setup will not stretch to cover it.
- Leadership is making technology calls without a technologist. Big decisions such as replacing the TMS or switching ELD providers are being made on demos and gut feel.
If three or more of those sound familiar, you have a leadership problem, not a tools problem. More software will not fix it.
What a fractional freight CIO actually does
The role is not mysterious. A good fractional CIO works on a regular cadence, sits in leadership conversations, and owns a defined set of responsibilities. Here is what a typical month looks like.
| Cadence | Activity | Output |
|---|---|---|
| Weekly | Check-in with the IT lead or MSP; review open issues, project status, and security alerts | Short status note; escalations handled before they become outages |
| Monthly | Leadership meeting with the owner, CFO, and operations manager | Updated technology roadmap, project dashboard, decisions log |
| Monthly | Vendor and spend review: TMS, ELD, EDI, telecom, licenses, support contracts | Spend register; renewals flagged ahead of auto-renew dates |
| Monthly | Risk review: backups, access, patching, MFA, and offboarding of departed staff | Risk register with owners and due dates |
| Quarterly | Roadmap and budget review against business goals | Reprioritized project list; next-quarter plan |
| Annually | Technology plan and budget for the coming year | Written plan the owner and CFO can approve |
Around that cadence, the fractional CIO leads whatever major work is underway. In a carrier, that often means:
- System strategy. Deciding whether to stabilize, optimize, or replace the TMS, and how ELD, EDI, imaging, and accounting should connect to it.
- Vendor selection and negotiation. Writing requirements, running demos with real scenarios from your freight, and reading contracts for data ownership, exit terms, and price escalators.
- Project oversight. Holding vendors and internal teams to scope, schedule, and budget on implementations and integrations.
- Security and continuity. Making sure backups are tested, access is controlled, and there is a plan for ransomware and outages.
- Data and reporting. Establishing one version of the numbers that operations, finance, and sales all trust.
- Managing the IT provider. Setting expectations for the managed service provider or internal IT staff, and reviewing their work.
- Translating for leadership. Turning technical choices into business terms: cost, risk, and effect on dispatch, billing, safety, and settlements.
Fractional CIO vs. MSP vs. full-time hire
These options are often confused, and the confusion leads to bad decisions. A managed service provider is not a CIO, and a CIO is not a help desk. Here is a plain comparison.
| Managed service provider | Fractional CIO | Full-time CIO | |
|---|---|---|---|
| Primary job | Keep devices, networks, email, and accounts running | Set technology direction, budget, and priorities; manage vendors and risk | Same as fractional, plus run an internal team day to day |
| Freight knowledge | Varies; often general business IT | Should be deep: TMS, ELD, EDI, rating, billing, settlements | Depends on the hire |
| Time commitment | Ongoing support, on call | Part time on a set cadence, more during major projects | Full time |
| Cost structure | Monthly fee, often per user or device | Monthly retainer or defined engagement | Executive salary and benefits |
| Accountable for | Uptime and ticket response | Business outcomes from technology | Business outcomes and team performance |
| Best fit | Every carrier needs this function somewhere | Carriers that need leadership but not a full-time executive | Larger carriers with internal IT and development teams |
Most carriers who bring in a fractional CIO keep their MSP or internal IT staff. The CIO does not replace them. The CIO gives them direction, holds them accountable, and makes sure their work serves the business. If you already have an MSP and wonder why things still feel unmanaged, that is usually why: they are doing exactly what they were hired to do, which is support, and nobody is doing strategy.
A full-time CIO makes sense when the volume of technology leadership work fills a week, every week. That usually happens when you run an internal development team, operate many terminals with local systems, or carry a large and constant project load. A fractional CIO can be the bridge: get the house in order, define the full-time role, and help you hire for it when the time comes.
The first 90 days
A fractional engagement should show its value early. Here is a reasonable plan for the first three months.
Days 1 to 30: Discover
- Interview the owner, CFO, operations, dispatch, billing, safety, payroll, and IT.
- Inventory every system, interface, vendor, contract, and renewal date.
- Review backups, access controls, and the most obvious security risks.
- Identify quick wins: a broken interface, an unused license, a renewal that should be renegotiated.
Days 31 to 60: Plan
- Deliver a written current-state assessment with ranked risks and opportunities.
- Draft a 12 to 18 month technology roadmap tied to business goals.
- Establish the monthly leadership meeting, project dashboard, and decisions log.
- Fix the most urgent risks, such as untested backups or departed employees with active accounts.
Days 61 to 90: Execute
- Kick off the first priority project with a scope, schedule, and owner.
- Set expectations and reporting with the MSP or IT staff.
- Present the first budget view: what you spend now, what the roadmap needs, and where to save.
How to measure a fractional CIO
You should be able to tell whether the engagement is working. Avoid vanity metrics and measure things the business cares about. Set a baseline in the first month so you can compare later.
| Area | What to measure | Why it matters |
|---|---|---|
| Projects | Projects delivered on scope, schedule, and budget | Stalled projects are the most common symptom of no leadership |
| Spend | Total technology spend, known and documented; renewals handled before auto-renew | You cannot manage what you cannot see |
| Risk | Restore tests passed, MFA coverage, open items on the risk register | Reduces the chance of a business-stopping outage |
| Operations | Re-keying eliminated, billing turnaround, settlement errors, manual workarounds retired | Shows technology is helping freight move and cash come in |
| Data | One agreed definition for key numbers such as revenue per mile and deadhead | Leadership decisions get made on trusted data |
| Leadership time | Hours the owner and CFO spend on vendor and IT issues | The owner should get time back, not lose more |
Ask for a short written report every month. If you cannot see progress in the roadmap, the risk register, and the project dashboard after a quarter, that is a real conversation to have.
Choosing the right fractional CIO
Technology leadership is not generic. A CIO who has only worked in retail or healthcare will spend months learning what a fuel surcharge table is, why a 214 status matters to your biggest shipper, or why settlement day is sacred. Ask candidates direct questions:
- Which transportation management systems have you worked inside, not just evaluated?
- Have you led a TMS go-live, a data conversion, or an EDI onboarding with a large shipper?
- How do you handle vendor relationships? Do you receive referral fees or commissions from any vendor you might recommend?
- Who will actually do the work, and how often will we see them on site?
- What will we have in writing after 30, 60, and 90 days?
- How do you hand off if we later hire a full-time CIO?
Independence matters. A CIO who earns commission on software or hardware has a conflict every time they recommend a purchase. You want someone whose only incentive is your result.
How Strong Tower Consulting helps
Strong Tower Consulting has worked with carriers since 2008 on training, implementations, upgrades, project management, and ongoing support. Our Fractional Freight CIO practice puts that freight-floor experience in your leadership meetings every month: roadmap, budget, vendors, risk, and projects, with a cadence and reporting you can hold us to.
That work connects naturally to our IT Strategy & Planning and Business & Technology Alignment practices, and when a major project starts, our Project & Program Management team can carry the day-to-day execution. Read more about how we work with clients.
Independent by design
Strong Tower Consulting never requires you to buy our software. As a third party, we are not selling you more products. We help you get more out of your existing investment, and if the answer is not more licenses or features, we will tell you.
Frequently asked questions
What is a fractional CIO?
A fractional CIO is an experienced technology leader who works for your company part time on an ongoing basis. They own the technology strategy, budget, vendor decisions, and risk, and they report to the owner or CFO, without the cost of a full-time executive.
Is a fractional CIO the same as a managed service provider?
No. A managed service provider keeps computers, networks, and accounts running. A fractional CIO decides what the business should run, sets priorities and budget, manages vendors including the MSP, and connects technology to dispatch, billing, safety, and settlements. Many carriers use both.
How much time does a fractional CIO spend with the company?
It depends on the size of the operation and what is underway. A steady-state engagement might be a few days a month with a standing leadership meeting, while a TMS selection or implementation year needs more. Scope is set up front and adjusted as projects start and finish.
When should a carrier hire a full-time CIO instead?
When technology work fills a full-time leadership role every week, such as running an internal IT and development team, managing many systems across multiple terminals, or carrying a large ongoing project portfolio. A fractional CIO can help define that role and recruit for it.
Will a fractional CIO from Strong Tower Consulting push us to buy Exspeedite?
No. Strong Tower Consulting is independent advisory. Consulting never requires buying our sister company's software, and vendor recommendations are based on your requirements.