AI Conversation Designer
We usually respond within three days
💷 Salary: £45,000 DOE
💼 Contract Type: 12 month FTC
🏢 Work Life Balance: Remote first with very occasional travel to Northampton
✈️ 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.
Ready to help redefine insurance?
We’re an award-winning business that’s changed how customers experience insurance. By challenging traditional thinking and raising the bar on service, we’ve built a reputation for doing things differently.
Our people are at the heart of that success. We invest in talent, back bold ideas and create space for innovation to flourish because growth happens when great people are empowered to do their best work.
With a global ambition to innovate, dominate and disrupt niche insurance markets, we’re looking for forward-thinkers who thrive on change and want to shape the future of the industry.
🌟 The Role:
Purpose of the role
This role owns the full lifecycle of conversational AI assistants across our Group brand portfolio, spanning digital and voice channels. You will design, build, test, launch, monitor, report on and iterate hybrid generative assistants, then expand proven approaches across additional brands once value has been demonstrated.
About the team
The Conversational AI Product squad own the hybrid generative virtual assistants, combining structured automation with generative AI to change how conversational services are delivered to customers. This role sits at the centre of that work, with a mandate to prove value in live customer-facing environments before scaling approaches further across the organisation.
🌟 What will you do?
Design conversational flows and hybrid generative assistant experiences for digital and voice channels, aligned to brand tone of voice and customer need.
Build assistants using enterprise conversational AI and generative AI tooling, including intent design, dialogue management and integration with existing digital systems.
Test assistants for accuracy, safety and tone consistency before launch, covering scenario and edge case testing.
Launch assistants into live, customer-facing environments across relevant brands.
Monitor live performance against defined success metrics, identifying accuracy, containment and customer experience issues as they arise.
Report on performance using auditable, evidence-based metrics rather than self-reported or anecdotal measures.
Iterate assistant design and logic based on live performance data and customer feedback.
Expand proven use cases across additional brands and channels once value is demonstrated.
Apply consistent design standards across a multi-brand portfolio, adapting tone and content to individual brand requirements.
Operate within a regulated environment, ensuring outputs meet FCA requirements including Consumer Duty obligations for customer communications.
Collaborate with technology, operations, compliance and brand stakeholders to align conversational AI work with wider business priorities.
🌟 Essentials:
Working understanding of conversation design principles, including flow design, dialogue management and tone of voice application.
Experience or demonstrable working knowledge of large language models and generative AI tools in a conversational context.
Ability to define, monitor and report on assistant performance using data rather than anecdotal evidence.
Strong written communication skills, with the ability to adapt tone of voice across different brand identities.
Experience working with cross-functional stakeholders, including technology, operations and compliance teams.
A customer-centred approach to problem solving, with awareness of accessibility and inclusive design principles.
Ability to manage multiple concurrent projects and priorities.
Comfort operating within a regulated environment where customer-facing outputs are subject to compliance oversight.
🌟 Bonus skills you may pack in your suitcase:
Hands-on experience designing, building and launching conversational assistants in a live, production, customer-facing environment.
Experience with boost.ai or a comparable enterprise conversational AI platform.
Experience extending conversational AI into voice channels, in addition to digital.
Experience training or tuning large language models against brand-specific tone of voice and guardrails.
Experience in a regulated industry such as financial services or insurance, with an understanding of the compliance implications of automated customer communication.
A track record of measurable business outcomes from conversational AI deployment, such as containment rate, deflection rate or customer satisfaction improvement.
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.
- Remote status
- Fully Remote
- Yearly salary
- £45,000
Insurance Meets Adventure!🚀
At Staysure Group, we’re not your typical insurance crowd. Our mission? To innovate, dominate and disrupt niche insurance on a global scale. Since 2004, we’ve been selling award-winning insurance products and services, proudly owning a portfolio of market-leading brands.
Our portfolio:
🌟 Staysure and Avanti: Specialising in crafting premium cover for the 45+ crowd, complete with pre-existing medical conditions
🌟 Payingtoomuch: Serves as a go-to price comparison platform, dedicated to helping customers secure the most competitive deals
🌟 Petgevity: Our furry friends deserve the best care, that's why we offer comprehensive insurance for both dogs and cats, ensuring that even those with pre-existing medical conditions are well protected
🌟 ROCK: Our B2B2C partnership travel insurance specialist

Why Staysure?
We excel in a vibrant and fast-moving atmosphere. Our secret sauce? Genuine care for our customers and our people. 🤝❤️
🏆 Awards Galore: We’ve won awards like “Best Travel Insurance Provider” (Moneywise) and “Employee Engagement Champion” (Employee Experience Awards) and many more! These achievements reflect our unwavering focus on excellence.
🚀 High-Growth: Joining us means stepping into a high-growth environment and being part of a vibrant team that encourages innovation and personal growth at every turn.
🎯 OKR Magic: Here, you will be empowered to set ambitious goals and achieve remarkable success in your position. The culture we foster is one of inspiration and motivation, ensuring that you are always challenged to grow and develop your skills.
Benefits of working with us
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Perkbox from day 1! 🎁
Discounts, bonuses and awards!
Perkbox also includes a fantastic suite of tools for looking after your mental wellbeing. -
Take some time for yourself 🛫
26 days paid holidays plus bank holidays, +1 day leave for every years service up to 30 standard days. And the option to buy more (Pro rata for FTC).
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Health and fitness, private medical insurance💪🏥
Following the successful completion of any probation period, membership to the company PMI & gym scheme is offered with the option to add additional family members (excluding less than 12 month contracts).
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Discounted travel insurance 🌴
Discounted travel insurance policies with Staysure.
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Pension 🏦
5% matched pension, auto enrolment after 3 months.
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Up to 5% company bonus💷
Earn up to 5% annual bonus. Depending on company and personal performance.
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Work hard, play hard 💃
Fantastic team social events, including parties and on-site social Fridays.
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Milestone gifts 📌
Up to 2 milestone gifts per year.
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Fancy food or a coffee? ☕️
A subsidised on site canteen and Costa Coffee in Northampton.
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Cycle to work 🚴♀️
We'll support you with costs if you're someone who likes to cycle to work.
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Giving back 🫶
We are committed to supporting our community and offer 1 day of volunteering a year for every employee.
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Employee assistance programme 💜
Health Assured who provide mental wellbeing support can be accessed through Perkbox.
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Fancy a change of scenery? 🏞️
With the option to work from anywhere, colleagues can enjoy the benefit of travelling to new destinations, new regions in the UK or visiting family abroad without using their annual leave entitlement for up to 2 weeks per year. This is subject to passing probation.