I started in criminal law in Wicklow, Ireland. It teaches you things about human behaviour, evidence and how people perform under pressure that no corporate training programme quite replicates. From there, corporate law, then construction and energy, then engineering and arbitration, then technology and outsourcing, now AI with quantum somewhere on the horizon if the literature I keep reading is any guide.

 Each move was driven by the same thing: genuine curiosity about where the complexity was heading next. Technology law looked niche in the early 2000s. AI law looked theoretical five years ago. Both turned out to be the centre of commercial legal practice. The pattern has been consistent enough that I have stopped second-guessing where my interests are pointing.

I have operated at Partner level at Matheson in London, one of Europe's leading law firms, leading a specialist technology and digital regulation practice advising international clients on high-value transactions and EU regulatory compliance across the AI Act, GDPR, DORA, NIS2, the Digital Markets Act and the Digital Services Act. Before that I served as Director of Legal Services at Accenture, a Fortune Global 500 company, where I led a team managing over £2 billion in annual contract value and personally structured and closed more than 150 major commercial transactions across 40 industries and multiple jurisdictions.

I have advised early-stage founders on their first commercial agreements and briefed Fortune 500 boards on strategic legal risk. The range is deliberate. A lawyer who has only ever worked in one sector or one type of client tends to give advice shaped by their experience rather than your situation. I have usually seen a version of what you are dealing with.

AI governance and commercial law is not a bolt-on to my data protection practice. It is where 20 years of commercial and technology law experience converges with what is now the defining legal risk for most businesses.

I am an AI Committee member of the Society for Computers and Law, accredited as a Leading IT Lawyer under the SCL's accreditation programme, and the author of AI Advantage: Thriving Within Civilisation's Next Big Disruption (2025) - a bestselling guide for C-suite leaders navigating AI risk. I am also a featured author on LexisNexis on AI contracting, and a regular speaker at the SCL Data Protection Conference, the Eyes-Off Data Summit, the AI Law Summit and LegalTechTalk.

The honest version: I was advising on technology contracting and digital regulation before AI became the topic of every board agenda. When it did, I had the foundation and the interest to go deep. That depth is what clients are engaging when they work with RMOK Legal on AI governance, EU AI Act compliance, and AI contract law. It is not a service line that was built because a client asked for it. It is where my career has been pointing for a decade.

For two decades I told founders, CEOs and boards that running a business is fundamentally straightforward. Get the strategy right, manage your risk, build the right team, and the rest follows. I said it with conviction because I believed it. 

In 2024 I decided to find out whether I actually believed it.

Building RMOK Legal has been the most clarifying professional experience of my career - not because it was harder than I expected, though it was, but because it made me understand from the inside what my clients have been dealing with all along. The cash flow decisions. The moment you realise the brand, the culture and every client relationship sits entirely with you. The gap between advising someone on a commercial risk and being the person who has to live with the outcome.

I have managed teams in private practice and in-house, worked across Ireland and the UK, and negotiated deals across four continents. None of that fully prepared me for what it means to be your own boss and understand the complete picture. I understand it now. And it changes how I work with clients who are living that reality every day.

There was also a structural problem I wanted to fix. The traditional hourly billing model is not accessible to many businesses that need senior legal support. Big firms charge rates that are designed for their cost base, not yours. AI tools, a hybrid working model, and no six-floor Mayfair office to fund mean the cost of delivering partner-level advice is materially lower here. That difference goes to the client.

I am more available than the traditional model would allow. Not just for the moments when a contract needs to close or a board presentation needs a legal input - but for the calls between those moments. The ones where a founder needs to think something through with someone who understands the stakes, without watching the clock.

 The relationships I build with clients are built on all of it - the good deals, the difficult negotiations, the moments where the right answer is uncomfortable, and the occasional piece of news that lands on a Friday afternoon and needs to be managed before Monday. That is where trust is actually built. Not in the pitch. 

Working with me is professional, honest, and - because we deal with enough pressure in running businesses - occasionally funny. I find the humour in what we do essential rather than unprofessional. A lawyer who makes every situation feel heavier than it needs to be is not doing you a favour.

I am direct. If the answer is not what you want to hear, you will hear it clearly and with an explanation of what to do about it. If a piece of work is outside my specialism, I will tell you that too rather than charge you while I learn.

Regulated and accredited

•     Solicitor regulated by the Solicitors Regulation Authority (SRA No. 8008227)

•     SCL-accredited Leading IT Lawyer - Society for Computers and Law

•     AI Committee member - Society for Computers and Law

•     Recognised in Legal 500 UK, Information Technology

•     2026 Business Elite Awards Winner

Published

•     Author: AI Advantage: Thriving Within Civilisation's Next Big Disruption (2025) - bestselling guide for C-suite leaders on AI risk

•     Featured author on LexisNexis: practical guidance on AI contracting clauses

•     Host: Beyond The Fine Print - tech law podcast for in-house counsel, Spotify, Apple Podcasts and YouTube

Speaking

•     SCL Data Protection Conference 2026, London

•     Eyes-Off Data Summit 2025, Dublin

•     AI Law Summit 2026

•     LegalTechTalk Conference, London

•     Platforum9

•     Guest on 6+ global podcasts in 2026 on AI law and the future of legal practice

Community

•     Trustee - The Solicitors' Charity

•     Trustee - Activity Alliance

•     Member - International Association of Privacy Professionals (IAPP)

•     Member - ITechLaw Association

Rory O'Keeffe is a solicitor regulated by the Solicitors Regulation Authority. This regulation applies to Rory personally as a solicitor. RMOK Legal Consulting Limited is not a law firm. SRA No. 8008227.

I am originally from Dublin, which means I came pre-loaded with an opinion on most things and a certain resistance to taking any of them too seriously.

I am married to a Brazilian, we have two boys, and between Irish, Brazilian and British culture, our household runs on a kind of negotiated pluralism that turns out to be genuinely useful professional training. I travel whenever the diary allows. I would recommend it, particularly to anyone who spends too much time advising on international transactions without experiencing the places those transactions involve.

I am a Trustee of The Solicitors' Charity and Activity Alliance - two roles that put me in rooms with people doing important work that has nothing to do with commercial law, which I consider one of the most useful things a lawyer can do for their own perspective. Trusteeship teaches you things about governance, accountability and what good leadership actually looks like that no number of board-level mandates quite replaces.