Head of Digital, AI Design

Role Overview

• Own and drive the digital and AI vision and roadmap, aligned to business strategy and client needs.
• Build, own and continuously evolve a prioritised pipeline of digital and AI initiatives, sequenced by value, effort, risk and strategic fit.
• Maintain an active, informed view of the AI and digital landscape and translate it into opportunities relevant to Waystone.
• Lead discovery and scoping of digital and AI initiatives across fund administration, compliance, onboarding, reporting and internal operations.
• Oversee the analysis of current-state operations and client journeys to inform future-state designs.
• Identify opportunities to streamline processes, reduce manual effort and improve data flow, guiding process re-engineering aligned with platform capabilities and compliance standards.
• Translate business needs and qualified opportunities into clearly defined solution concepts — scope, intended outcomes and success measures — ready to hand to delivery teams.
• Drive structured requirements gathering and solution design that bridges business needs and technical delivery, with clear acceptance criteria.
• Champion user-centric design across digital and AI solutions, using concepts, journey maps and lightweight visuals to communicate intent.
• Lead, develop and inspire a team of digital and AI solution designers and application owners.
• Create a high-performance, inclusive team culture built on trust, accountability, collaboration and continuous improvement.
• Invest in team members’ development through coaching, career planning, skills training and performance feedback.
• Foster psychological safety and open communication, supporting both individual wellbeing and collective achievement.
• Define clear goals and priorities, ensure team alignment to business objectives, and remove blockers to success.
• Collaborate with stakeholders across Compliance, Operations, IT, Product and Client Services to ensure alignment and prioritisation of digital and AI initiatives.
• Champion the adoption of digital and AI tools across the ManCo business, building organisational appetite and understanding.
• Act as a key liaison between business and technology teams, translating operational needs into clear, actionable requirements.
• Track expected versus realised value of initiatives and feed the learnings back into the roadmap.
• Ensure digital and AI opportunities are shaped with appropriate regard to regulatory, data protection, security and responsible-AI considerations from the outset.
• Partner with Risk, Compliance, Legal and Information Security — and with delivery teams — to ensure initiatives are deliverable within the firm’s control framework.
• Work closely with Product, IT and vendors to select, optimise and shape solutions on core platforms (e.g., Salesforce, Appian, the Microsoft / Azure estate, fund administration systems, client portals and workflow automation).

Requirements

• Proven experience leading digital transformation, digital/AI design or operational digitisation in financial services, ideally in fund administration, asset management, or ManCo services.
• Strong background in discovery, business and systems analysis, process design, solution design and roadmap ownership.
• Demonstrated ability to identify and shape technology, digital and AI opportunities and translate them into well-defined solutions.
• Demonstrated success in building, leading and developing high-performing teams.
• Ability to shape and sustain a positive, inclusive and growth-oriented team culture.
• Excellent interpersonal skills, with the ability to coach, mentor and support individuals at different levels.
• Strong understanding of business operations and client workflows in a regulated financial environment.

Tech Stack

• Azure

Benefits

• Professional development
• Flexible work arrangements