Hastings Direct
Head of Challenger Pricing
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Head of Challenger Pricing (Telematics)
Hybrid, with a minimum of one day per week at one of our main sites in Bexhill, Leicester, or London
We’re a fast-growing digital insurer serving more than four million customers, with ambitious plans for the UK market and significant investment across our insurance and telematics businesses, underpinned by market-leading pricing and data capability.
Joining a small, focused innovation team, you’ll challenge how we price risk by exploring new methodologies, segmentation approaches, and data sources that can outperform our existing strategy.
With best-in-class data, tools, and implementation capability, you’ll have the freedom to test bold ideas and the support to scale successful innovations across the business.
Role overview
Challenge and outperform our existing motor pricing strategy by developing new pricing methodologies, sharper risk segmentation, and innovative uses of data—including telematics and behavioral insight—to improve risk selection and commercial performance.
Success will be measured by your ability to turn pricing innovation into measurable value. You’ll identify, test, and prove challenger approaches that improve pricing sophistication, create new risk signals, and unlock the potential of telematics and alternative data alongside our established rating capabilities.
Working through our established pricing organization, you’ll partner with Pricing, Data, and Analytics teams to move successful concepts from experimentation into live pricing. Your challenge is simple: outperform our current approach from the inside and strengthen how Hastings prices risk at scale.
Challenger Pricing Strategy
- Develop and maintain a portfolio of challenger methodologies with intent to avoid overlap with our existing incumbent approach
- Continuously identify opportunities to outperform existing pricing approaches
Experimentation & Test and Learn
- Design and execute controlled pricing experiments working with the existing team to execute them into a live environment
- Explore new approaches to risk selection and customer segmentation
Alternative Data & New Risk Signals
- Explore the use of telematics, behavioral, and non-traditional data sources – don’t constrain yourself to what we use today or even what we have
- Identify new signals that improve pricing precision and customer selection
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Skills and experience we’re looking for
- Strong experience in insurance pricing, predictive modelling, or advanced analytics, ideally within motor or telematics
- Hands-on technical capability using Python, R, SQL, or similar analytical tools to work with large and complex datasets
- A track record of challenging established thinking and developing innovative, data-led approaches
- Strong problem-solving skills, with the ability to form clear hypotheses, design robust tests, and translate findings into action
- Comfort working with ambiguity, building from first principles, and taking ideas from concept through to implementation
- Strong commercial judgement and a clear understanding of how pricing decisions influence risk selection, customer value, and portfolio performance
The journey with us
Our straightforward interview process is designed to help us get to know each other and give you a clear picture of the role:
- Initial conversation with our recruiter
- Introductory discussion with the hiring leader
- Case study interview with the hiring leader
- Final conversation with a senior leader
As a Disability Confident employer, we’re committed to ensuring our recruitment processes are fully inclusive – what this means to you is if you’re applying for a job with us, you’ll have fair access to support and adjustments throughout your recruitment journey. We also welcome applications through the Disability Confident Scheme (DCS). For more information on the DCS, please visit our inclusive business page on our careers website.
Benefits
In addition to a competitive salary and a £6k car allowance, you will also receive…
- Flexible working – we champion a flexible hybrid working approach – please speak to your recruiter to discuss in more detail
- Competitive bonus scheme - all colleagues are eligible for our annual 4Cs performance bonus
- Physical wellbeing – as a Band 5 colleague, Hastings pays for you to receive private medical insurance (also known as PMI). This gives you flexibility and convenience to see a specialist or consultant and allows you to decide when and where you will be seen
- Financial wellbeing – as well as providing you with 4x your salary with our life assurance cover, income protection at no extra cost, and matched pension contributions up to 10%, we are proud to provide you with an award-winning package which includes – discounts, cashback, free independent mortgage advice, and free access to financial wellbeing support
- Mental wellbeing programme – we have the thrive mental health app, our colleague assistance programme available 24/7, our own in-house mental health first aiders, support groups, and a dedicated team to make sure we are covering your needs
- There's more! – 27 days annual leave + bank holidays, with the option to buy or sell one of your weeks, access to our healthcare cash back plans, dental plans, discounted health assessments, Cycle to work and tech schemes, discounted and free onsite facilities, social events throughout the year, and much more …
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Join us
Join us and you’ll find a different way of doing things. We call it the 4Cs. We focus on getting it right for our colleagues, customers, company, and community. As one of our colleagues, you’ll be helping to drive our growth, so in return, we’ll give you all the support, training, and development you need.
Our 4Cs principles are simple: we believe by creating the right culture for our colleagues and giving them the right tools to do their job, we’ll deliver good outcomes for every customer, helping us to grow the company profitably and sustainably and allowing us to invest in the communities we serve.
Hastings Group
Hastings Group is an equal opportunities employer which means we treat people fairly. We welcome applications from all suitably skilled persons regardless of their gender, age, race, disability, ethnic background, religion/belief, sexual orientation, gender reassignment, or marital/family status. Please also note that we have a thorough referencing process, which includes credit and criminal record checks.
At Hastings Direct, we’re committed to creating an inclusive environment where everyone has the opportunity to succeed. If you require any reasonable adjustments during the recruitment process, we encourage you to be open with us. Our recruitment team is here to provide the support you need to ensure a fair and accessible experience for all.
Job posting end date
17/09/2026
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