Anna Pitsillides is Head of Product at Winston Taylor, where she leads technology product strategy and helps shape the firm’s approach to AI and emerging technologies. With expertise across product management, AI and legal technology, Anna focuses on identifying opportunities, evaluating new technologies and translating complex business needs into practical, user-focused solutions. Her work spans the full product lifecycle, including proof-of-concept initiatives, strategic buy-versus-build decisions, implementation, adoption and measuring value. She works closely with business leaders, technology teams and external partners to ensure innovation delivers tangible outcomes for both the firm and its clients. Anna also has a strong focus on responsible AI adoption, balancing innovation with appropriate governance, security and compliance. Her focus is on using technology and AI to empower people, improve how legal services are delivered and create measurable business and client value.