As generative AI moves from experimentation into everyday legal work, in-house teams are discovering that technology alone does not solve the service-delivery challenge.
They need greater speed, cost control and visibility—without compromising the accuracy, expertise and trust on which legal work depends. In response, the traditional boundaries between law firms, alternative legal service providers and technology companies are beginning to blur.
ClearyX operates at the centre of that shift. A subsidiary of Cleary Gottlieb Steen & Hamilton LLP, the independently operated business brings legal professionals and software engineers together to deliver transactional diligence, legal operations support and technology-enabled solutions. Its model combines the resources and substantive expertise of a global law firm with the flexibility to develop new technologies and ways of working outside a traditional firm structure.
In this interview with LegalTech.ca, Caitriona Robinson, Vice President of Client Engagement at ClearyX, discusses how client expectations are reshaping legal service delivery.
ClearyX sits at an interesting intersection between BigLaw, legal operations, and technology. How do you explain its role to clients who may still think of legal service delivery in traditional law firm terms?
CR: Five years ago, Cleary Gottlieb looked at how quickly technology was maturing and made a deliberate decision to build something new. ClearyX was incorporated separately so it could operate on its own terms, hire differently, and build its own technology. Our connection to the firm gives us a foundation of legal excellence and client trust that most legal tech companies simply cannot replicate.
The client conversation has moved on as well. It used to be “should we use an ALSP?” Now it is “what combination of law firm, technology and specialist delivery solves this problem?” We bring experienced legal professionals and software engineers into the same team, and the work spans transactional diligence, contract intelligence and legal operations. Initially, we focussed on delivering tech-enabled legal services using third-party tools. The technology piece came later, partly because we realised we could build products in house, with the features and workflows that our clients are asking for, and this led us to launching two proprietary products this year, CX+Transact and CX+Insights.
As Vice President of Client Engagement, what are you hearing most often from in-house legal teams about where they need support today?
CR: General Counsel have the same pressures as every other executive. They’re expected to move faster, manage risk, embrace AI and often do it with flat or shrinking budgets. We’re seeing that they don’t often ask whether a piece of work should go to a law firm, an ALSP or a tech company. They ask: “How do I get this transaction completed quicker?” “How do I understand my risk across this portfolio?” “How do I scale this process without hiring a large team?” That’s fundamentally changing how legal work is delivered. Historically, clients chose lawyer firms because of expertise, reputation and relationships. Those things still matter. But today they’re also asking: Can you provide better visibility? Can you generate data and insights? Can you work as an extension of our legal team?
ClearyX describes itself as blending talent and technology to deliver tech-enabled legal and business solutions. Where are clients seeing the clearest return on that model?
CR: ClearyX combines legal talent with AI-powered diligence solutions, delivering consistent cost and time savings. Ranked as a legal tech leader in Chambers & Partners, the team’s diligence work typically costs 40-60% less than traditional associate review and can be completed in 40–60% less time. The team also creates custom AI-powered legal operations solutions, contract review (NDA’s, leases, LPA’s, side letters, finance agreements, etc.), automation, custom client portals, and analytics.
For years legal teams generated huge amounts of information, with limited insights. AI changes that and suddenly the data sitting inside thousands of contracts becomes something organizations can use to inform decisions. For example, when you complete a transaction, you can now generate structured intelligence that informs integration, compliance, future acquisitions and commercial decision-making. Because this work underpins real transactions, reliability is non-negotiable. CX+ uses the power of LLMs but removes the unpredictability. The product is engineered so that the model operates within defined boundaries – it retrieves, extracts, and analyses based on the actual content of the documents, rather than generating free-form responses. The result is accuracy clients can rely on, at scale.
How has the rise of generative AI changed client expectations around speed, cost, transparency, and outcomes in legal work?
CR: Clients are no longer looking for discrete legal advice on one hand and a separate technology solution on the other. They want a single solution with commercial understanding layered on top.
What has not changed is the expectation of accuracy. If anything, the stakes have risen because the tools are more powerful and errors can propagate faster. We manage that risk through systematic quality control: running identical queries across multiple models, comparing outputs to flag anomalies, and catching behavioural drift in the AI before it reaches a client-facing deliverable. The narrative around AI replacing lawyers has been unhelpful. The real opportunity isn’t replacing expertise – it’s removing the repetitive, process-heavy work that prevents lawyers from spending time where they create the most value. The winners won’t be organizations with the best AI. They’ll be organizations that combine AI with experienced legal professionals in a way that clients trust.
That said, the cost picture is more nuanced than the headlines suggest. Token costs have risen as models become more powerful and data volumes increase. The organizations that maintain a cost advantage will be the ones that route work intelligently. That engineering discipline is core to how we have built CX+.
ClearyX is independently operated but owned by Cleary Gottlieb. How does that structure help you innovate differently than a traditional law firm practice group might?
CR: The hardest part of innovating in legal services is not the technology, it is getting people to change how they work. ClearyX was set up outside the firm to enable exactly that. We are fully remote, we staff flexibly, and we have the freedom to build our own technology from the ground up when off-the-shelf tools are not fit for our purpose.
ClearyX exists because Cleary Gottlieb is itself an innovative firm. The firm has a strong track record of investing in innovation, both internally, in terms of how its lawyers work, and externally, in terms of how it delivers value to clients. The decision to create ClearyX was a natural extension of that mindset. The former Managing Partner, Michael Gerstenzang, saw where the market was heading, committed real resources, and gave us the mandate and the sustained sponsorship to build something genuinely different, and that support continues at the firm today. When our product team is building out a use case for a specific industry or practice group, we leverage the expertise of the firm in the design and workflows. That feedback between the people building the software and the people who understand the substance is not something most legal tech companies can replicate. The combination of operational independence and that level of substantive access is what makes the tech and solution distinctive.
Many legal teams are experimenting with AI tools, but turning pilots into practical workflows remains difficult. What separates successful adoption from stalled experimentation?
CR: Three points come to mind – alignment, design and trust.
- Alignment: adoption has to be a business strategy, not a side project run by a champion in legal operations.
- Design: the tool has to work, and demonstrate value immediately; it has to connect to documents where they already sit, and it has to be designed around how lawyers actually work, not retrofitted from something built for a different audience.
- Trust: Technology doesn’t spread in our industry solely because it’s powerful. It spreads because someone trusted made it feel safe, and because the workflow around it was designed to succeed. Legal has always been built on trust. AI doesn’t remove that, if anything, it raises the bar. Clients need confidence not only in the advice they’re receiving, but in how AI is being governed, validated and supervised.
What kinds of legal work are best suited to tech-enabled delivery today, and where do you still see human judgment as irreplaceable?
CR: Anything involving extraction and pattern recognition across large document volumes is where technology delivers the most immediate value. Contract portfolio analysis, due diligence, NDA review. Turning thousands of static agreements into a queryable, visual data layer is the kind of transformation that only software can deliver at scale.
But there is always a need for a human in the loop. AI is excellent at surfacing risks, extracting data and identifying patterns, but it takes legal and commercial judgement to turn that raw output into reliable, actionable advice. That is a core principle of how we work at ClearyX. Our technology is built to handle the volume and the repetition so that legal teams can focus on the work that actually requires their expertise, with direct access to Cleary Gottlieb’s substantive knowledge behind them.
Looking ahead, what do you think legal service delivery will look like five years from now — and what should legal leaders be preparing for today?
CR: The industry is moving towards integrated legal delivery. Clients will not think in terms of law firms versus ALSPs versus technology vendors. They will assemble ecosystems where different providers contribute different strengths depending on the problem, and success will come from collaboration rather than competition. Legal leaders who are preparing for that future need to be making decisions now about their technology infrastructure, their data strategy, and how they want to work with external partners.
ClearyX was built to support this evolving model – we are not a law firm trying to adopt technology, and we are not a technology company trying to understand law. We sit at the intersection, with the backing of Cleary Gottlieb and proprietary technology we have built from the ground up.