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Jason Westwood. IT Director for hire.

24 years building and running the IT function of one £65m UK SME. Statutory company director. Now doing the same job, fewer days a week, for other owner-managed businesses.

The long version

I joined a UK SME as a junior in the early 2000s. The business had about 350 staff and a homegrown line-of-business system running on a niche legacy database most people had never heard of. Over the next two decades the business grew to around £65m turnover across multiple sites, and I grew with it — from the person fixing everyone’s printers to the person sitting on the board as IT Director and statutory company director.

In that time I did most of the things a UK SME IT Director does. Replaced a 20-year-old unsupported legacy database with a modern platform, without a day of downtime. Stood up Active Directory, then virtualised everything, then moved half of it to the cloud. Rolled out Microsoft 365 and made SharePoint genuinely work for the business rather than sitting unused. Brought mobile device management in when the estate needed it. Built customer-facing portals. Consolidated a sprawl of suppliers back into something the finance team could actually manage.

I also spent years being the person the board turned to on cyber. Took the business through Cyber Essentials Plus on first attempt and maintained it every year since. Stood up MFA and EDR before either was fashionable in the SME market. Sat opposite cyber insurers at renewal and explained why our posture justified their premium.

More recently I’ve been doing IT due diligence on live acquisitions — looking at target businesses pre-deal, identifying what’s hiding in their estate, and giving the deal team a real technical view to work with.

Why I set up Westwood Digital

Over the years I’ve spoken to a lot of other directors of SMEs between roughly £10m and £150m turnover. They almost always have the same problem: they know IT matters to their business, they know they’re not getting enough senior attention on it, and they can’t justify a full-time IT Director on £100k-plus plus package. So they make do. The MD runs IT in their head. Or the FD does. Or the COO does. Or nobody does, and the MSP quietly makes the strategic calls by default.

None of those are good answers. What those businesses actually need is a real IT Director, with real experience, for one or two days a week. Or for a fixed stretch during a vacancy. Or for a specific piece of work. That’s what Westwood Digital is for.

What I’m good at

  • Sitting in front of a board and explaining IT in language non-technical directors can act on.
  • Holding suppliers to account. MSPs, software vendors, telecoms, consultants — I’ve been on the buying side of all of them and know how the conversations go.
  • Cyber Essentials Plus, MFA, EDR, patching, backup, the unglamorous controls that actually matter.
  • Picking the right battles. Most SMEs don’t need a transformation programme; they need three or four specific things done properly.
  • Migrating off legacy platforms without breaking the business.
  • Building Power BI dashboards that directors actually use rather than the monthly PDF nobody reads.
  • Having the uncomfortable conversation — with the MD, with the FD, with the supplier — when that’s what the situation needs.

What I’m not

  • An IT support shop. If you need someone to fix a printer, that’s not me.
  • A generalist management consultant. I don’t produce slide decks full of frameworks.
  • A reseller. I don’t take commissions on kit, software, or services. Advice is paid for by you, owed to you.
  • A developer. I’ve managed developers for years, but I’m not going to write your code.

How I work

First person, peer to peer. I’ll tell you what I think, explain why, and stand behind it. If I don’t know something I’ll say so. If I disagree with you I’ll tell you that too, and we’ll work it out.

I bill for time I work, against an agreed scope. I don’t lock clients into long contracts — if it’s not working you exit with reasonable notice, and so do I. Most engagements that start well carry on for a long time because both sides want them to, not because a contract forces it.

If you’ve read this far and you’re wondering whether I’m the right person for what you’re dealing with, the quickest way to find out is to send me a short note about your situation. I’ll tell you honestly whether I can help.

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