David Woolstencroft has worked in legal technology since 2002, beginning as a co-founder of DocsCorp before later founding Novum Global, where he is CEO. Novum Global focuses on legal technology talent across law firms, legal tech companies and related businesses worldwide. Woolstencroft also co-founded the People in Legal podcast, giving him regular exposure to both employers and professionals considering their next career move. Throughout the session, his focus was clear: understanding how technology is changing not only the tools lawyers use, but the work they are expected to perform, and helping professionals build the combination of legal, technical and commercial skills needed to remain valuable.

Overview

Woolstencroft described AI as a more fundamental shift than previous waves of legal technology. Earlier tools improved how lawyers worked, whereas AI is starting to change what they do by handling tasks such as research, drafting, summarisation and information collation. Adoption is increasingly client-driven, with firms receiving AI-prepared materials and clients expecting a higher starting point. Junior lawyers are also experimenting with AI tools, creating pressure for change from both inside and outside firms.

This shift is driving demand for hybrid roles such as legal engineers. Employers want professionals who understand legal workflows and can apply AI and technology to practical problems. Crucially, qualifications alone are not enough; candidates need to demonstrate applied capability through real examples such as workflows or tools they have built. The strongest profile combines deep legal expertise with the ability to use technology effectively within a specialism.

The discussion also highlighted implications for junior lawyers and career development. As AI reduces routine training work, firms will need new ways to build judgement and commercial awareness, with client exposure offering one route. Key skills increasingly include communication, technical capability, curiosity and commercial understanding. Woolstencroft’s advice was to specialise, build strong AI capability, understand how legal businesses operate, develop networks and remain adaptable rather than focusing too narrowly on a job title.

Key Takeaways

• AI is changing the substance of legal work, not simply making existing processes faster.
• Hybrid legal-tech roles are becoming increasingly valuable, especially where legal knowledge is combined with practical technology skills.
• Demonstrable experience matters: employers want to see what candidates have built, improved or solved, not just what courses they have completed.
• Communication, curiosity and commercial understanding are critical differentiators alongside legal and technical expertise.
• Junior lawyer training will need to evolve as AI absorbs more routine tasks, with client exposure offering one route to developing judgement and practical knowledge.
• Build a portfolio of complementary skills rather than relying on a job title: specialise, understand AI, learn the economics of legal businesses, develop relationships and keep experimenting.