About

Home/About
About

Jason Westwood. Fractional CIO & IT Director.

24 years building and leading IT within a £65m UK business, the last seven as IT Director and statutory Board member. Named in the CIO 100 UK 2026. I now bring that experience to other owner-managed businesses that want technology to create value, not simply add cost.

Jason Westwood, Fractional CIO and IT Director

The long version

I joined a UK SME as Network Manager in the early 2000s and grew with the business, progressing to Head of IT and then IT Director. Since 2019, I’ve also served as a statutory Board member.

During that time the business grew to around £65m turnover across multiple sites, and my role changed with it. What started as responsibility for technology became responsibility for making sure technology supported what the wider business was trying to achieve.

That has meant modernising core systems, building and developing teams, managing significant budgets, challenging suppliers, improving resilience, reducing cost and using technology to improve the way the business operates and serves its customers.

I’ve led major system changes, replaced legacy platforms without disrupting the operation, introduced new digital services and reporting, consolidated suppliers and helped turn technology from something viewed primarily as a cost into something expected to create measurable business value.

And because I sit on the board as a statutory director, I understand the other side of those decisions too. Investment has to compete with everything else the business wants to spend money on. Risk has to be understood rather than exaggerated. Suppliers need to be held accountable. And ultimately technology has to contribute to growth, efficiency, customer service or resilience. Otherwise, you have to question why you’re doing it.

Cyber security has been part of that responsibility too. I’ve led the business through Cyber Essentials Plus, strengthened its security and resilience, and dealt directly with insurers, suppliers and the board on cyber risk. But I see cyber in the same way I see the rest of technology: as a business risk to understand and manage, not an IT project in isolation.

I’ve also worked on IT due diligence around acquisitions, looking at the technology estate, people, contracts, licensing, security, cost and the work likely to be required after a transaction.

Why I set up Westwood Digital

Over the years I’ve spoken to plenty of owners and directors of SMEs who face the same challenge.

Technology matters more and more to the business, but there isn’t always somebody around the board table with the experience to challenge what is being spent, whether suppliers are delivering, whether the current systems are still right, where the real risks sit or what should happen next.

Sometimes that falls to the MD or FD. Sometimes it falls to an internal IT manager who should be focused on delivery. And sometimes the MSP ends up influencing strategy simply because nobody else is taking ownership of it.

Westwood Digital gives businesses access to experienced technology leadership without having to employ another full-time executive.

That might mean a short independent review to understand where things stand, a defined piece of work around a specific problem, interim leadership during a period of change, or an ongoing fractional role working alongside the existing management team.

My job is ultimately pretty simple: understand what the business is trying to achieve, work out whether technology is helping or getting in the way, and make sure the money being spent on it is creating value.

What I’m good at

  • Helping boards understand where they should spend, where they can save and what can wait.
  • Challenging suppliers, contracts and costs and making sure the business is getting what it is paying for.
  • Turning complicated technology issues into clear decisions for MDs, FDs and boards.
  • Understanding risk without turning everything into a crisis or a compliance exercise.
  • Working out which three or four things genuinely matter instead of creating a huge transformation programme.
  • Leading significant system and organisational change without losing sight of the day-to-day business.
  • Having the difficult conversation when something isn’t working, whether that’s with a supplier, a colleague or the board.

I also have the technical depth to get underneath an issue when necessary. I’ve spent my career around infrastructure, applications, cyber, data, development and business-critical systems, so I’m not reliant on a supplier telling me whether something is technically sound.

What I’m not

  • An IT support company. I’m there to provide leadership, challenge and direction, not run a helpdesk.
  • A generalist management consultant. I don’t arrive with a framework and produce a slide deck that nobody uses.
  • A reseller. I don’t make money from the products or suppliers I recommend. My advice is paid for by you and owed to you.
  • Someone looking to create work for the sake of it. Sometimes the right answer is to leave something alone.

How I work

First person, peer to peer.

I’ll understand what the business is trying to achieve before recommending what technology should do about it. I’ll tell you what I think, explain why and stand behind it. If I disagree with something, I’ll say so. If I don’t know something, I’ll say that too.

I work remotely on a fixed fee, agreed day rate or ongoing retainer depending on what the work actually needs.

For new clients, that will often start with a short, fixed-fee discovery review. It gives me enough time to understand the business, the current technology position, suppliers, spend and the main areas of risk or opportunity before either of us commits to anything bigger.

Sometimes that review is all the client needs. Sometimes it identifies a specific piece of work worth doing. And sometimes I stay involved fractionally to help the business deliver it.

The point is to prove value first, not sell you the biggest engagement I can.

If you’re wondering whether I could help with what you’re dealing with, send me a short note about the situation. I’ll tell you whether I think I can add value.

Start a conversation →

Scroll to Top