Wordsmith has appointed Simon McCarthy as Vice President of Transformation, expanding its enterprise transformation capabilities as generative and agentic AI reshape how legal teams operate.
McCarthy brings 15 years of experience in legal technology and transformation and has worked across more than 150 enterprise Contract Lifecycle Management and legal transformation programs spanning financial services, pharmaceuticals, manufacturing, healthcare and other complex industries.
He joins Wordsmith from ContractPodAI, where he most recently led Enterprise Transformation. His prior roles include Director of Contracting Transformation Services at KPMG UK and Director of Product Management at Exari, which was later acquired by Coupa. McCarthy also founded CLM Nexus, an independent advisory business focused on CLM strategy and transformation.
The appointment comes as Wordsmith expands its work with global enterprises and builds services around the organizational changes required to deploy AI effectively within legal departments. The company sees the challenge increasingly shifting from selecting individual software features toward determining which legal processes should be redesigned, what can be automated, where human judgment should remain and how organizations can manage risk while achieving measurable business outcomes.
In his new role, McCarthy will lead Wordsmith’s enterprise transformation capability and work with customers and partners across strategy, solution design, implementation, adoption and value realization.
The transformation function will help enterprises assess their current maturity, establish target operating models for AI-enabled legal services, identify and prioritize high-value use cases, redesign workflows, develop governance frameworks and establish measures for evaluating results.
McCarthy’s appointment follows a period of significant growth for Wordsmith. The company recently raised a $70 million Series B followed by a $14 million Series B extension, bringing the combined financing to $84 million. Wordsmith also said revenue has increased 14-fold year over year and its platform is now used by more than 500 customers, including BT, Financial Times, Sage, Starling, Deliveroo, Canva and Safelite.
KEY QUOTES:
“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.”
Simon McCarthy, VP of Transformation at Wordsmith
“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.”
Ross McNairn, Co-Founder and CEO of Wordsmith
