💷 Salary: £100,000 - £110,000
💼 Contract Type: 12 month FTC
🏢 Work Life Balance: Hybrid, 1 day 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 shape the future of travel insurance and customer experience at scale?
Staysure Group is looking for a commercially driven, customer-obsessed Head of Product to lead product strategy, prioritisation, and transformation across our growing ecosystem of brands and business lines.
You’ll own the enterprise product roadmap, leading a team of Product Managers to deliver measurable growth, better customer experiences, and AI-enabled innovation across digital and operational journeys.
Define and deliver product strategy aligned to growth and transformation goals
Own and prioritise the enterprise-wide product roadmap
Drive improvements across acquisition, quote & buy, servicing, claims, pricing, and retention
Lead major strategic transformation initiatives (“Big Bets”)
Use data, experimentation, and AI-driven insight to maximise customer and commercial value
Build and develop a high-performing product team
Partner with senior stakeholders across Commercial, Marketing, Pricing, Insurance, Design, Data, and Technology
Proven experience leading product teams in complex digital, ecommerce, insurance, fintech, or consumer businesses
Strong commercial mindset with a passion for customer experience
Expertise in roadmap prioritisation, experimentation, and data-led decision making
Confident stakeholder manager with the ability to influence at senior level
Experience driving transformation and leading cross-functional delivery teams
Exposure to AI-enabled products, automation, or modern product operating models is a plus
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.

At the home of travel insurance, we strive to be
the best at what we do.
Over 700 people work across our brands and our head office is in Northampton and have another office in the heart of London. We inspire, motivate and empower our employees to be the very best through a clear vision and live by the Staysure Group values.
We constantly strive to nurture our people and improve our products and services to make what we have to offer the best-in-class. We are proud that our efforts continue to be recognised year after year with a number of industry awards, such as the British Travel Awards and The Personal Finance Awards.