Head of AI Systems & Enablement

💷 Salary: £120,000 DOE + Bonus and Car Allowance

🏢 Work Life Balance: Hybrid

✈️ Candidate Journey: Our goal is to reply to applications within 3 working days. Additionally, we make sure to acknowledge, evaluate, and respond to all applications as a way of showing our appreciation for your time and effort in applying to us.

Are you ready to join an award-winning business that is reshaping the insurance landscape? Our organisation has transformed the way customers interact with insurers, establishing a benchmark for exceptional service. With our recent digital transformation, we are eager to find passionate and motivated individuals to join us on our journey to success.

We firmly believe that attracting and developing talented professionals is essential for our ongoing growth and success. By investing in our team, we create an environment where innovation thrives and opportunities abound.

Our aim is to innovate, dominate and disrupt niche insurance on a global scale, which means we are seeking innovators and individuals who embrace change with ease. Together, we can drive change and make a significant impact in the industry.

🌟 The Role:

This is a senior leadership role responsible for driving Group-wide AI enablement, data science, and activation. You will lead the development of our AI strategy, shape investment priorities, and oversee the systems, models, and capabilities that embed AI into how we operate, discover, and deliver value. This includes leadership of our internal data science function, ensuring the right problems are being solved, with the right methods, and at the right level of impact.

We believe that competitive advantage in AI starts with data. Not just volume, but access, structure, quality, and governance. The organisations that win will be those who best use their data to power insight, experimentation and automation at scale. This role is accountable for ensuring that our AI systems are built on a strong data foundation, partnering with the Head of Data (Product & Infrastructure) to ensure AI readiness by design, and with Data Science to drive strategic use case delivery.

Working closely with the CDIO and cross-functional partners, you will translate ambition into action, ensuring we are strategically aligned, technically equipped and ethically prepared to scale AI across the business. You will also be the primary lead for aligning AI investment with strategic priorities, owning the roadmap for where and how AI is deployed across the Group.

🌟 What will you do?

Strategic AI leadership:

• Define and continuously refine the Group-wide AI strategy, prioritising where to play and how to win.

• Lead the strategic AI investment framework: establish principles and criteria for which

AI initiatives we fund and scale.

• Translate market trends and technology shifts into proactive advantage, not reactive catch-up.

Enterprise enablement and system design:

• Build and oversee scalable AI infrastructure: orchestration platforms, retrieval augmented generation (RAG), vector databases, AI agents, fallback systems, and observability tooling.

• Ensure platform capabilities are modular and reusable across business units and brands.

• Govern and optimise the full AI lifecycle: from experimentation through to operationalisation.

Cross functional alignment:

•Partner with Product and Technology to embed AI into experiences, not just processes, enabling co-pilot systems, intelligent customer journeys and adaptive operations.

• Collaborate with Data teams to ensure AI is built on well-governed, accessible, and high-quality data products.

• Work with Legal, Risk, and Compliance to uphold AI safety, explainability, and regulatory alignment (e.g. FCA and GFSC readiness).

Discovery and culture enablement:

• Develop internal tooling, sandboxes, and frameworks to accelerate AI experimentation at the edge (squads, brands, functions).

• Sponsor AI literacy programmes and best-practice sharing to build a fluent and confident organisation.

• Champion a “discovery-first” mindset across squads and leaders balancing safety with velocity.

🌟 Essentials:

• Proven experience leading AI or data strategy at enterprise scale.

• Strong technical fluency across LLM ecosystems, orchestration tooling, and scalable AI infrastructure (LangChain, OpenAI, Anthropic, vector DBs, etc)

• Deep understanding of AI governance, explainability, and ethical compliance, especially in regulated sectors

• Demonstrated success building operating models and cross-functional collaboration in a matrix org

• Clear ability to bridge commercial insight, customer value, and technical feasibility

🌟 Bonus skills you may pack in your suitcase:

• Experience in insurance, financial services, or regulated data environments

• Exposure to operational and customer-facing AI applications (e.g. GenAI, automation, intelligent agents)

• Familiarity with AI safety frameworks (e.g. ISO/IEC 42001, model carding, fallback strategy design

We’re assembling a diverse team, where skills, not checkboxes, reign supreme, regardless of race, religion, sex, sexual orientation, gender identity or disability. 

Staysure Group welcomes all new starters with open arms, providing training, development opportunities, and great benefits.