Find a job 
Featured Companies 
Featured Universities 
For Companies At a Glance
- Tasks: Lead AI strategy and enablement across the organisation, driving innovation and operational excellence.
- Company: Join an award-winning business transforming the insurance landscape with cutting-edge technology.
- Benefits: Enjoy a hybrid work-life balance, competitive salary, bonuses, and a supportive team culture.
- Why this job: Be part of a dynamic team reshaping the industry, fostering innovation and making a real impact.
- Qualifications: Proven experience in leading AI strategy, strong technical skills, and a deep understanding of AI governance.
- Other info: We value diversity and inclusion, welcoming all applicants regardless of background.
The predicted salary is between 84000 - 168000 £ per year.
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. We acknowledge, evaluate, and respond to all applications to appreciate your effort.
Are you ready to join an award-winning business that is reshaping the insurance landscape? Our organisation has transformed customer interactions with insurers, setting a benchmark for exceptional service. With our recent digital transformation, we seek passionate and motivated individuals to join us on our journey to success. We believe attracting and developing talented professionals is essential for our growth. By investing in our team, we foster an environment where innovation thrives and opportunities abound. Our aim is to innovate, dominate, and disrupt niche insurance globally, seeking innovators who embrace change. Together, we can drive change and make a significant industry impact.
The Role: This senior leadership role drives Group-wide AI enablement, data science, and activation. You will develop our AI strategy, shape investment priorities, and oversee systems, models, and capabilities that embed AI into our operations, discovery, and value delivery. You will lead our internal data science team, ensuring the right problems are addressed with suitable methods and impact. We believe competitive AI advantage starts with data—volume, access, structure, quality, and governance. Success lies in leveraging data for insight, experimentation, and automation at scale. This role ensures our AI systems are built on a strong data foundation, partnering with the Head of Data and Data Science teams to ensure AI readiness and strategic use case delivery. Working closely with the CDIO and cross-functional partners, you will translate ambitions into actionable strategies, ensuring alignment, technical readiness, and ethical compliance for AI scaling across the business. You will also lead AI investment alignment and deployment roadmaps.
What will you do?
- Strategic AI leadership: Define and refine the Group-wide AI strategy, prioritising initiatives. Lead the AI investment framework, establishing funding principles. Translate market trends into strategic advantages.
- Enterprise enablement and system design: Build scalable AI infrastructure: orchestration platforms, RAG, vector databases, AI agents, fallback systems, observability tools. Ensure platform capabilities are modular and reusable. Govern and optimise the AI lifecycle from experimentation to operationalisation.
- Cross-functional alignment: Partner with Product and Technology to embed AI into experiences and operations. Collaborate with Data teams for high-quality, accessible data products. Work with Legal, Risk, and Compliance to uphold AI safety and regulatory standards.
- Discovery and culture enablement: Develop tooling, sandboxes, and frameworks for AI experimentation. Sponsor AI literacy programmes and best practices. Promote a discovery-first mindset across teams.
Essentials:
- Proven experience leading AI or data strategy at enterprise scale.
- Strong technical fluency in LLM ecosystems, orchestration, and scalable AI infrastructure (LangChain, OpenAI, Anthropic, vector DBs).
- Deep understanding of AI governance, explainability, and ethics, especially in regulated sectors.
- Success in building operating models and cross-functional collaboration.
- Ability to bridge commercial insight, customer value, and technical feasibility.
Bonus skills:
- Experience in insurance, financial services, or regulated data environments.
- Exposure to operational and customer-facing AI applications.
- Familiarity with AI safety frameworks (ISO/IEC 42001, model carding, fallback strategies).
Diversity and inclusion: We value skills over checkboxes, welcoming individuals regardless of race, religion, sex, sexual orientation, gender identity, or disability. Staysure Group offers training, development, and great benefits.
Head of AI Systems & Enablement employer: Staysure Group
Contact Detail:
Staysure Group Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land Head of AI Systems & Enablement
✨Tip Number 1
Familiarise yourself with the latest trends in AI and data science, especially those relevant to the insurance industry. This knowledge will help you engage in meaningful conversations during interviews and demonstrate your passion for the field.
✨Tip Number 2
Network with professionals in the AI and insurance sectors. Attend industry events, webinars, or online forums to connect with potential colleagues and learn about the challenges they face, which can give you insights to discuss during your application process.
✨Tip Number 3
Showcase your leadership skills by sharing examples of how you've successfully led AI initiatives or cross-functional teams in the past. Be prepared to discuss your approach to building scalable AI infrastructure and fostering collaboration across departments.
✨Tip Number 4
Understand the ethical implications of AI in regulated environments. Be ready to discuss how you would ensure compliance and governance in your strategies, as this is crucial for the role and will set you apart from other candidates.
We think you need these skills to ace Head of AI Systems & Enablement
Some tips for your application 🫡
Tailor Your CV: Make sure your CV highlights relevant experience in AI leadership and data strategy. Use specific examples that demonstrate your technical fluency and ability to drive AI initiatives at an enterprise scale.
Craft a Compelling Cover Letter: In your cover letter, express your passion for AI and how it can reshape industries like insurance. Discuss your vision for AI enablement and how your background aligns with the company's goals.
Showcase Relevant Skills: Emphasise your understanding of AI governance, explainability, and ethics. Mention any experience you have with LLM ecosystems and scalable AI infrastructure, as these are crucial for the role.
Highlight Cross-Functional Collaboration: Provide examples of how you've successfully collaborated with different teams, such as Product, Technology, and Data. This will demonstrate your ability to align AI strategies across various functions within an organisation.
How to prepare for a job interview at Staysure Group
✨Understand the AI Landscape
Familiarise yourself with the latest trends in AI, especially those relevant to the insurance sector. Be prepared to discuss how these trends can be leveraged to create strategic advantages for the company.
✨Showcase Your Leadership Experience
Highlight your previous experience in leading AI or data strategy at an enterprise scale. Provide specific examples of how you've successfully managed cross-functional teams and driven AI initiatives.
✨Demonstrate Technical Fluency
Be ready to discuss your technical knowledge of LLM ecosystems and scalable AI infrastructure. Prepare to explain how you would approach building and optimising AI systems within the organisation.
✨Emphasise Ethical AI Practices
Given the importance of governance and ethics in AI, be prepared to talk about your understanding of AI safety frameworks and how you would ensure compliance with regulatory standards in your role.
