Paul Middleton MAICD
Business technology consultant for small service businesses · Process first, AI where it helps · illawarra.ai · Wollongong
Based in Australia · 25+ years experience
Summary
Founder, illawarra.ai · AI strategy, safe use, and practical implementation for owner-directors and small businesses. Member of the Australian Institute of Company Directors. IAPP AIGP candidate.
About
I've spent 25 years building things: a 12-year international ecommerce business across four countries, product roles spanning martech startups and global SaaS, and a string of independent platforms and tools built alongside my day job.
In June 2026 I founded illawarra.ai to help owner-directors and small businesses put AI to work safely and sensibly.
Running my own business taught me what a bad technology decision costs when it's your money on the line. Product leadership taught me to evaluate software carefully and to start with the outcome, not the tool. And years working on business intelligence and prioritisation software taught me that most technology projects fail not because of the tool, but because the data isn't ready and the priorities aren't clear.
That's where I start with clients: working out what's worth doing, checking whether the data and processes are ready, and putting AI to work in ways that change how the business runs. I also help them look ahead at how AI could reshape their industry, so time spent improving today's tasks isn't wasted on work that may not exist in a few years. And I don't do AI for the sake of it: if there's a better option that doesn't use AI, I'll tell you.
I still build. Recent projects include an AI chat assistant for photomojo, my photography experience marketplace, and AI tool integrations for DOMAINSAFE, my domain licensing and management business, so I can check domain details from whichever AI assistant I'm working in. I build with the OpenAI and Claude APIs, Cursor, and OpenClaw. I have been taken payments through Stripe for myself and marketplace suppliers since 2017.
Based in Wollongong, working across the Illawarra, Greater Sydney, and online. Always happy to talk with business owners thinking about AI, or anyone interested in product management as a career.
I have recently attended the AICD Company Directors Course and am training towards the IAPP AIGP certification, which I hope to achieve before the end of 2026.
Skills
Regions covered
Industry experience
Professional Services, Retail, SaaS
At a glance
Paul brings hands-on experience across Governance & Risk, Data & AI. Available for engagements across New Zealand, Australia. Industry experience includes Professional Services, Retail, SaaS.
How fractional CTO engagements with Paul work
Paul works on a fractional basis — typically one to three days a week for an agreed engagement length — so you get senior technical leadership without the cost or commitment of a full-time hire. Engagements commonly include technical due diligence, board reporting, engineering team leadership, technology strategy, architecture reviews, hiring support, and stepping in as interim CTO during a transition.