Salary: £70,000, 10% bonus and a car allowance Location: Northampton/Hybrid Role Type: Permanent ✈️ 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. Interview Process: TBC At Staysure Group, we are on an ambitious growth journey to enhance our customer experiences, empower our colleagues, and drive sustainable success across multiple brands. To achieve these objectives, we have aligned over 50 transformation initiatives under five strategic pillars: Growth – Core, Challenger, Comparison & Partnership brands Product, platform, and customer journey transformation Customer and employee operations transformation Security, compliance, and regulatory transformation Business optimisation The Transformation Function ensures the effective design, delivery, and management of the Group Transformation Portfolio. We collaborate with a cross-functional community that spans Technology, Product, Finance, and other critical areas to deliver innovative and impactful outcomes. About the Role The Head of Core Brands Delivery for Staysure and Avanti will be responsible for translating commercial priorities into a structured portfolio of initiatives that drive customer acquisition, engagement, retention, and renewal. Reporting to the Group Head of Transformation Delivery, this individual will work closely with key trading stakeholders across the Staysure Group to shape and execute a delivery roadmap that turns commercial hypotheses into tangible business outcomes. This role requires deep expertise in the travel insurance and insurance markets combined with strong commercial acumen and a delivery-focused mindset. The ideal candidate will bridge the gap between commercial strategy and execution, ensuring initiatives are successfully taken from idea through discovery, design, and delivery. Key Responsibilities Commercial Delivery & Strategic Execution Lead the development and execution of a delivery roadmap aligned with the commercial objectives of Staysure and Avanti. Translate commercial priorities into structured initiatives that drive measurable business value. Ensure alignment between trading, marketing, product, and technology teams to maximise impact on customer acquisition, engagement, retention, and renewal. Build and maintain a robust portfolio of initiatives, ensuring clarity on objectives, scope, timelines, and expected outcomes. Stakeholder Collaboration & Influence Work closely with key trading stakeholders to identify opportunities for growth and customer experience enhancement. Act as the bridge between commercial, product, technology, and transformation teams, ensuring a clear understanding of business goals and how they translate into execution. Provide senior leadership with regular insights, reporting, and recommendations on portfolio performance and commercial impact. Delivery & Execution Excellence Drive initiatives from idea through discovery, design, and delivery, ensuring they are effectively executed and deliver on expected outcomes. Implement structured governance and prioritisation frameworks to manage competing priorities and ensure resources are allocated effectively. Proactively identify risks, dependencies, and challenges, ensuring timely resolution and course correction where necessary. Ensure initiatives are measurable, with clear KPIs and tracking mechanisms in place to assess success and ROI. Industry Expertise & Market Insight Leverage deep knowledge of the travel insurance and broader insurance markets to shape commercially viable initiatives. Stay ahead of market trends, competitor activity, and regulatory changes, ensuring strategic initiatives remain relevant and competitive. Provide thought leadership on customer trends, digital innovation, and operational efficiencies in the insurance space. Skills and Experience Essential Extensive experience in the travel insurance and/or broader insurance market, with a strong understanding of customer behavior, product dynamics, and competitive landscape. Proven ability to translate commercial strategies into structured initiatives and execution roadmaps. Strong commercial acumen, with a track record of delivering initiatives that drive customer acquisition, engagement, retention, and renewal. Experience in managing cross-functional delivery portfolios, working across commercial, product, marketing, and technology teams. Exceptional stakeholder management and influencing skills, with the ability to engage at all levels of the business. Data-driven mindset, with the ability to define success metrics, track performance, and iterate based on insights. Strong problem-solving and decision-making abilities, with a focus on execution excellence. Desirable Experience working within a multi-brand organisation or group structure. Familiarity with agile methodologies and product-led delivery approaches. Knowledge of customer experience (CX) and digital transformation principles. We’re assembling a diverse team, where skills, not checkboxes, reign supreme, regardless of race, religion, sex, sexual orientation, gender identity or disability. Our compass points to inclusion. Staysure Group welcomes all new starters with open arms, providing training, development opportunities, and great benefits.