ABOUT JAYWING
Jaywing is a data, creative, and technology agency that helps organisations navigate complexity and unlock growth. We bring together strategy, experience design, analytics, and technology to deliver work that is both commercially effective and genuinely useful to the people it serves.
We work closely with a select group of enterprise clients, often embedding senior capability directly into their teams to help shape and deliver complex transformation programs.
ABOUT THE CLIENT
This role sits within a large, nationally recognised organisation currently undergoing a significant digital transformation.
Given the nature of the work, we’re keeping the client confidential at this stage. What we can share is that the organisation operates at enterprise scale, manages a portfolio of brands and services, and is investing heavily in improving how customers engage across its digital ecosystem.
The transformation is not cosmetic. It involves rethinking core customer journeys, modernising platforms, and embedding a more product-led, experience-driven approach across the business. The environment is complex, highly visible, and commercially meaningful.
THE ROLE
This is not a project manager role. It is not a delivery co-ordinator role. It is a senior leadership position for someone who connects digital experience decisions directly to business outcomes and has the credibility to make that case in a boardroom.
As Digital Transformation Lead, you will be embedded within the client’s environment on behalf of Jaywing, acting as a senior trusted advisor to their leadership team. You will maintain a program-level view across a multi-stream transformation portfolio, ensuring initiatives are scoped, sequenced, and measured against outcomes that matter — conversion, engagement, revenue contribution, and operational efficiency.
UX/UI sits at the centre of this role. You will treat experience design as a commercial lever, not a layer applied at the end. You’ll be equally comfortable discussing interaction logic with designers as you are articulating ROI and performance impact to executive stakeholders.
You will operate across multiple complex initiatives simultaneously, bringing structure, clarity, and momentum without adding noise. You’ll challenge assumptions where needed, navigate ambiguity with confidence, and help turn complexity into clear, actionable decisions.
This role suits someone who is energised by shaping direction, not just delivering against it.
KEY RESPONSIBILITIES
Strategy and Roadmap Leadership
- Partner with senior stakeholders to shape and evolve the digital transformation roadmap
- Translate strategic ambition into clearly defined, prioritised initiatives with measurable outcomes
- Maintain a program-level view across multiple workstreams, balancing long-term opportunity with near-term delivery realities
Conversion-Led Experience
- Position UX/UI as a driver of commercial performance, not just usability
- Embed CRO thinking into initiatives from the outset
- Define measurement frameworks that link experience improvements to tangible business outcomes
- Ensure customer journeys are intuitive, frictionless, and grounded in behavioural insight
Stakeholder Engagement
- Act as a senior point of alignment across business, technology, design, and delivery teams
- Lead workshops and strategic discussions with clarity and authority
- Challenge inefficiencies and assumptions constructively, offering better alternatives
- Simplify complexity and enable confident decision-making
Program Enablement
- Ensure initiatives are well-shaped, outcome-driven, and ready for delivery
- Identify and remove structural or process barriers slowing progress
- Maintain visibility of the broader transformation without stepping into day-to-day delivery management
- Support faster iteration by reducing dependencies and decision bottlenecks
Organisational Excellence
- Maintain clear, traceable documentation across decisions and program structure
- Apply systems thinking to sequencing, prioritisation, and stakeholder alignment
- Model the level of clarity and discipline expected across the program
REQUIRED EXPERIENCE
Non-negotiable
- Senior experience leading digital transformation in complex enterprise environments
- Strong UX/UI capability with a conversion and performance mindset
- Hands-on experience with CRO methodologies (A/B testing, funnel analysis, etc.)
- Ability to operate strategically without becoming embedded in delivery detail
- Experience working closely with executive stakeholders
- Proven ability to manage multiple complex initiatives concurrently
- Experience in multi-vendor or hybrid delivery environments
Highly regarded
- Experience with AEM or similar enterprise CMS platforms
- Strong understanding of analytics platforms such as GA4 or Adobe Analytics
- Background in agency or embedded partner roles
- Experience owning or leading a CRO program
- Familiarity with modern product and delivery models
WHAT SUCCESS LOOKS LIKE
In the first 90 days, you will have built strong relationships with key stakeholders, developed a clear view of current experience performance, and identified a small number of high-impact optimisation opportunities with a strong commercial case.
At six months, you will be operating as a trusted advisor. Experience decisions will be grounded in data, and performance metrics will be embedded into how success is measured. You will be influencing roadmap priorities and helping shape executive-level decisions.
Ongoing success means measurable improvements in both customer outcomes and commercial performance, with experience investment clearly linked to ROI.
WHY THIS ROLE
- Work on a genuinely complex, high-impact transformation program
- Operate at a senior level with access to executive stakeholders
- Be embedded within a client environment while supported by Jaywing’s broader capability
- Influence direction, not just delivery
- Hybrid working model: a mix of onsite collaboration and flexibility
- Join a team that values clarity of thinking, not just activity
If this is the opportunity that you’ve been looking for, click APPLY NOW and attach your CV and a cover note letting us know why you’re the best applicant for this role.
