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Legal technology veteran joins Wordsmith to build its enterprise transformation capability as AI reshapes how legal teams operate.
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We’re announcing today that we have appointed Simon McCarthy as VP of Transformation, bringing one of the legal technology industry’s most experienced transformation leaders into our business as we expand our work with global enterprises.
Simon joins us with 15 years of experience in legal technology and transformation and has worked across more than 150 enterprise Contract Lifecycle Management (CLM) and legal transformation programmes spanning financial services, pharmaceuticals, manufacturing, healthcare and other complex industries.
He joins us having worked across every side of enterprise legal transformation: leading change from within corporate legal teams, building legal technology products, advising organisations as a consultant, and helping technology vendors deliver complex transformation programmes.
We’re welcoming Simon from ContractPodAI, where he most recently led Enterprise Transformation. Previously, he was Director of Contracting Transformation Services at KPMG UK and Director of Product Management at Exari, which was subsequently acquired by Coupa. He also founded CLM Nexus, an independent advisory business focused on CLM strategy and transformation.
We’re making this appointment as generative and agentic AI changes both what legal technology can do and what enterprises need from their technology providers.
As AI platforms become increasingly powerful and configurable, we see the challenge for legal teams shifting from selecting software features to deciding where and how AI should change the way legal work gets done: which processes to redesign, what to automate, where human judgement should remain, how to manage risk, and how to turn new capabilities into measurable business outcomes.
As Simon explains, this changes both the questions legal teams need to ask and the role technology providers must play.
“The technology has reached a point where it can be configured to do extraordinary things. The hardest question is no longer simply what the product can do - it’s what we should do with it. AI is blurring the traditional boundary between product and transformation. Vendors need to understand the operating model they’re helping to create, not just the technology they’re deploying. And that means working differently with both customers and partners, bringing together deep product knowledge, transformation expertise and the specialist capabilities needed to make change successful at enterprise scale.”
Ross McNairn, our co-founder and CEO, said the appointment reflects our ambition to take greater responsibility for the outcomes our technology creates.
“We’re not asking legal teams to buy another piece of software. We’re giving them the ability to fundamentally rethink how legal work happens across their organisation. That makes transformation expertise incredibly important. Simon has spent his career on the customer, consulting, product and vendor sides of this problem. He understands how to connect technology to operating-model change and measurable outcomes and how vendors, customers and partners need to work together to make that change stick.”
Simon will lead our enterprise transformation capability, working with our customers and partners from the earliest stages of strategy and solution design through implementation, adoption and value realisation. Through this function, we’ll help enterprises understand their current maturity, define the target operating model for AI-enabled legal services, identify and prioritise high-value use cases, redesign processes, establish governance and define clear measures of success.
We’re making this appointment after a period of rapid growth. We recently announced a $70m Series B and subsequent $14m Series B extension. We’ve grown revenue 14x year-on-year, and more than 500 customers now use our platform, including BT, FT, Sage, Starling, Deliveroo, Canva and Safelite.
