Head of Digital & AI Design

About Waystone

Waystone is a leading asset-servicing solutions provider of institutional governance, administration, risk and compliance services to financial institutions. With over 25 years’ experience and a comprehensive range of specialist services to its name, Waystone helps our clients structure, operate and grow through our expertise, innovation and digitisation, backed by the operational scale to support global expansion

Summary

Reporting to the Chief Technology Officer, the Head of Digital and AI Design will be an integral part of the team’s and organisation’s success.

We are seeking an experienced and forward-thinking leader to own the design of our digital and AI agenda - finding where digital and AI can create value across the ManCo business, shaping those opportunities into well-defined solutions, and building and owning the roadmap that brings them to life.

This is a design, discovery and roadmap leadership role. The Head of Digital and AI Design leads a team that identifies opportunities, re-engineers processes, and defines solutions to the point they can be handed to delivery teams to build - owning the “what” and the “why”, while delivery owns the “how”. A core focus of the role is developing a high-performance team culture, championing individual growth, team wellbeing, and a strong sense of shared purpose, all within the control standards expected of a regulated financial services environment.

Key Responsibilities

Digital & AI Strategy and Roadmap

• 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.

Opportunity Discovery & Process Re-engineering

• 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.

Solution Design & Definition

• 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.

Team Leadership, Culture & Development

• 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.

Stakeholder Engagement & Change Leadership

• 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.

Governance & Responsible AI

• 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.

Digital Platform & Systems Oversight

• 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).
• Support the integration of systems to create seamless, scalable and secure digital ecosystems.
• Ensure data consistency, integrity and compliance with regulatory standards.

Skills & Experience

• 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.
• Excellent communication, stakeholder management and change leadership skills.

Desirable

• Experience with platforms such as Salesforce, Appian, Microsoft Azure / M365, fund administration systems, or workflow automation tools.
• Awareness of generative AI, intelligent automation and agentic capabilities and their practical applications.
• Familiarity with discovery, roadmapping and prioritisation techniques.
• Familiarity with Agile / Lean methodologies and digital delivery frameworks.
• Knowledge of compliance, regulatory and reporting obligations in fund services.

Personal Attributes

• Curious, with a natural eye for spotting opportunities.
• Strategic thinker with a focus on long-term business outcomes.
• Strong problem-solving abilities and decision-making skills.
• Comfortable balancing innovation with the control needs of a regulated firm.
• Ability to work under pressure and handle multiple priorities.
• Collaborative and able to work across departments.