Head of Insurance Proposition
We usually respond within three days
💷 Salary: Up to £88,500 DOE
💼 Contract Type: Permanent, full time
🏢 Work Life Balance: Hybrid, at least once per month at our Northampton office
✈️ 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:
We’re looking for an experienced Head of Insurance Proposition to lead the strategy, development and performance of our insurance product portfolio.
This is a high-impact role where you’ll own the product vision and roadmap, ensuring our propositions meet customer needs, remain competitive and support our wider commercial ambitions. You’ll work closely with senior stakeholders, partners, underwriters and teams across the business to bring new products and propositions to market and continuously improve what we offer.
🌟What you’ll be doing
Own and deliver the insurance proposition strategy, vision and roadmap.
Lead and prioritise the product backlog, turning business objectives and customer insight into actionable outcomes.
Identify opportunities to improve, grow and monetise our products and services.
Use market, competitor and customer insight to shape our proposition and identify new opportunities.
Partner with senior stakeholders, underwriters and third-party distributors to deliver new products and enhancements.
Lead product launches, including requirements, testing, change management and implementation.
Ensure products deliver fair value and strong customer outcomes, with appropriate governance and conduct risk considerations.
Build strong relationships across Product, Development, Operations, Design, Partnerships and Commercial teams.
Help develop the capability and talent within the insurance proposition team.
🌟What we’re looking for
You’ll be an experienced Product or Proposition leader who can combine strategic thinking with hands-on delivery. You’ll be confident managing multiple priorities, influencing senior stakeholders and turning complex requirements into clear, commercially focused outcomes.
You’ll bring:
Proven experience leading multiple products, propositions or teams.
Strong product management and product development experience.
Excellent stakeholder management and influencing skills.
Strong commercial, analytical and problem-solving ability.
Experience managing dependencies, risks, priorities and delivery.
Excellent communication and organisational skills.
A collaborative leadership style and a passion for developing people.
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.
- Locations
- Northampton
- Remote status
- Hybrid
- Yearly salary
- £80,000 - £88,500
- Employment type
- Full-time
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.