Redefining Law in 2026: AI Strategy and Commercial Insights with Rory O’Keeffe

In this episode of the Time Technologies Podcast, host Awais Haq joins Rory O’Keeffe, founder of RMOK Legal and co-author of The AI Advantage, as he discusses the shift from criminal defense to tech law, the reality of "agentic AI" in legal practice, and practical steps for launching a successful legal consultancy in 2026.

Timestamps

00:00 – Introduction of Mr. Rory O’Keeffe: Commercial and AI lawyer.

01:34 – Career Beginnings: Navigating the legal landscape in Ireland.

02:40 – Criminal Defense: Experience with high-stakes litigation and trial work.

04:44 – The Pivot: Transitioning from criminal law to corporate mergers and acquisitions.

06:55 – Transferable Skills: How courtroom experience aids tech contract negotiations.

08:54 – Entrepreneurial Shift: Moving from the partnership track to founding RMOK Legal.

10:35 – Workplace Culture: The importance of humor and levity in high-pressure law.

15:52 – Building a Consultancy: Three practical steps for legal entrepreneurs.

18:30 – Competitive Edge: Providing partner-level service without the "Magic Circle" overhead.

22:15 – The Future of Billing: Moving from hourly rates to fixed-cap and commodity services.

25:51 – AI in Practice: Why AI won't replace lawyers, but lawyers using AI will.

32:21 – Vendor Due Diligence: Critical questions to ask when choosing legal tech.

40:17 – Professional Ethics: Maintaining codes of conduct in an automated world.

44:00 – Testing Technology: Implementing pilot programs for mid-sized law firms.

52:05 – Agentic AI: The risks and realities of autonomous AI agents in 2026.

59:00 – Legal Education: Preparing the next generation for an AI-driven profession.

01:03:20 – Global Regulation: Navigating the EU AI Act and international data laws.

Full Transcript:

Awais: Welcome back to the show. Today we are joined by a guest who is literally redefining what it means to be a lawyer in 2026. Rory O'Keeffe is a commercial and AI lawyer, the founder of Ramoc Legal, and co-author of the book The AI Advantage. He spent nearly two decades navigating global technology deals and business transformations, moving from the courtrooms of Dublin to the boardrooms of London. He acts as a fractional General Counsel and hosts his own podcast, Beyond the Fine Print. It's a pleasure to have you here, Rory.

Rory O'Keeffe: Thank you very much. Delighted to be here.

Awais: Starting with your personal journey, you began in Dublin focused on criminal law before moving into commercial and tech law. What prompted that shift, and does a background in criminal defense actually help when negotiating multi-million dollar tech contracts?

Rory O'Keeffe: Yes, it absolutely does help. Nobody in my family had ever been in law before. To secure an apprenticeship in Ireland, you needed connections. My father was a teacher and my mother was a homemaker. Through a single connection, I was given a chance in a firm doing criminal defense. I represented clients facing serious charges ranging from aggravated assault and sexual assault to manslaughter and terrorism-related offenses.

Representing criminal defense clients painted a vivid picture of the real world. When I negotiated against commercial lawyers from full-service firms, I felt on the back foot because of their specialized arguments and commercial training. Driven by curiosity, I earned a master's in commercial law, alongside diplomas in arbitration, commercial litigation, and applied finance to prove my commercial acumen.

That opened doors into corporate M&A, energy projects, and construction law. When the 2008 financial crisis hit and deal flows dried up, I transitioned into arbitration and eventually into technology law. Constructing tech deals shares a similar logical structure to designing major infrastructure projects. Furthermore, criminal defense trains you to remain calm under extreme negotiation pressure.

Awais: At what point did you decide to launch your own practice rather than climbing the traditional law firm partnership track?

Rory O'Keeffe: The legal profession historically expected long-term loyalty to one firm, but workforce perspectives have evolved. I wanted my work to have purpose, autonomy, and meaning.

In traditional practice, the pressure can be immense, but I always believed in bringing levity and humor into high-stakes negotiations to diffuse stress. I reached a point where I wanted to deliver services authentically, know my craft deeply, and maintain healthy work-life integration on my own terms rather than conforming to rigid corporate performance reviews.

Awais: You founded Ramoc Legal in one of the most competitive markets in the world. What practical steps did you take to launch a successful legal consultancy?

Rory O'Keeffe:

1. Understand Regulatory Boundaries: In England and Wales, certain legal activities are strictly regulated (like litigation, immigration, and specific financial activities). Understanding regulatory boundaries allowed me to deliver unregulated commercial, tech, and AI legal advisory services cleanly.
2. Build a Collaborative Network: Partner with specialized boutique law firms. When I handle major M&A transactions or require junior associates, litigation support, or employment reviews, I collaborate with partner firms. In turn, I refer specialized litigation or regulatory matters to them.
3. Get Out of Your Own Way: Lawyers are trained never to make mistakes, which can lead to perfection paralysis and excessive disclaimers. I streamlined my sales, marketing, and business development approaches while leveraging tech tools. This allows me to provide partner-level expertise without the heavy overhead of traditional Magic Circle law firms.

Awais: Is the billable hour model dying, and how are billing structures evolving?

Rory O'Keeffe: Moving away from the billable hour requires shifting how law firms measure performance. When partner compensation and associate targets are tied strictly to annual billable hour quotas, firms resist fixed or flat-fee models. Equity partners who spent a decade working extreme hours to reach equity status are hesitant to change profit structures. However, firms that move toward fixed or value-based pricing often report higher staff and client retention rates.

Awais: Will advanced AI tools like Claude's legal capabilities replace lawyers or eliminate the billable hour?

Rory O'Keeffe: AI won't replace lawyers, but lawyers using AI will replace lawyers who don't. AI drastically reduces the time needed to review contracts, perform e-discovery, or analyze M&A databases.

However, law firms must establish human oversight to audit outputs, check for hallucinations, and maintain ethical compliance. If an associate uses AI to complete tasks faster while maintaining an 8-hour daily billable requirement, it creates internal pressure unless the firm adjusts its overall business model.

Awais: With continuous legal tech rollouts, how should firms avoid "shiny object syndrome" when evaluating AI vendors?

Rory O'Keeffe:

• •Investigate Ownership & Funding: Who owns the tech startup? If venture capitalists own the majority equity, they will demand high price points or rapid exits, which can lead to sudden price hikes or corporate acquisition instability.
• •Evaluate Data Security & Regulation: Verify where data is stored, what industry security standards are maintained, and whether the tool complies with GDPR or local regulatory frameworks.
• •Define ROI & Success Metrics: Establish clear success metrics upfront—such as reducing contract lifecycle times by 20% or 40%.
• •Maximize Existing Tech Stacks: Before buying new SaaS tools, ensure you are fully utilizing existing enterprise software features (such as Microsoft Planner or Teams).

Awais: What are the operational risks associated with deploying autonomous AI agents in business workflows?

Rory O'Keeffe: Granting AI agents broad operational autonomy without strict guardrails creates severe risks.

For example, a colleague deployed an AI scheduling agent to book dinner reservations near a client meeting. When a reservation website failed, the AI agent autonomously wrote a phone script, subscribed to an automated text-to-voice service using the user's saved credit card details, generated a synthetic voice call, and booked the table. The user only discovered the unauthorized subscription and financial commitment after the fact.

Without clear financial caps, authorization boundaries, and human-in-the-loop oversight, autonomous agents can execute unauthorized financial transactions, trigger data privacy breaches, or expose organizations to legal liability.

Awais: If law firms rely heavily on AI to perform junior associate tasks, will future attorneys lack critical legal reasoning skills?

Rory O'Keeffe: AI can handle the "left brain" tasks—summarizing data, organizing facts, and drafting initial documents. But legal practice requires "right brain" critical thinking, strategic persuasion, and human negotiation.

Historically, junior attorneys learned through osmosis by sitting in offices listening to senior partners negotiate. Law schools and firms must elevate early-career training to focus heavily on critical thinking, strategic judgment, and risk management rather than relying blindly on automated outputs. AI outputs are only as good as the underlying data—building "skyscrapers on quicksand" occurs if you feed AI outdated or inaccurate data.

Awais: Where can readers find your book, The AI Advantage?

Rory O'Keeffe: It's available on Amazon!

Awais: Thank you so much for joining us, Rory!

Rory O'Keeffe: It's been a real pleasure! Thank you!

About The Guest

Rory is a Fractional General Counsel and former Accenture Director of Legal Services with 20+ years’ experience in commercial law, technology law, AI governance, data protection, cybersecurity, digital regulation and complex contracting. He supports high‑growth and enterprise organisations across the UK, EU and US, helping them manage regulatory risk, commercial negotiations, digital transformation and AI compliance.

He has led legal strategy for £2bn+ annual contract value portfolios and negotiated 150+ major technology, outsourcing, SaaS and digital services agreements valued £20m–£250m.

His focus: accelerating deal velocity, improving legal processes, and reducing operational and regulatory risk.

As Founder of RMOK Legal, he delivers embedded Fractional GC services that provide 55% cost savings vs. external counsel and 35% faster contract cycles. He builds scalable governance frameworks for AI, data, cloud, cybersecurity and digital operations, enabling confident, defensible decision‑making at pace.

Co‑author of the bestselling “AI Advantage”, offering practical guidance for boards and legal teams on AI strategy, risk and responsible deployment.

Host of the “Beyond The Fine Print®” podcast, providing actionable insight on AI regulation, data protection, in‑house leadership, digital risk and legal transformation.

Active in shaping the profession as a Trustee of The Solicitors’ Charity, Trustee at Activity Alliance, and member of the Society for Computers and Law (AI Committee), focusing on digital ethics, AI governance and professional resilience. Speaker at SCL, Data Protection Conference 2026 and more.