At a Glance
- Tasks: Lead the growth of an innovative insurtech business and shape its future.
- Company: Join a dynamic startup backed by a leading insurance group.
- Benefits: Enjoy 31+ days of annual leave, enhanced parental pay, and wellbeing support.
- Other info: Flexible working options and a commitment to inclusivity.
- Why this job: Be at the forefront of transforming insurance for delivery drivers in the gig economy.
- Qualifications: 5-10+ years in strategy or commercial leadership with a hands-on approach.
The predicted salary is between 63000 - 77000 £ per year.
Location: Hybrid with office days in Liverpool (option to work some office days from London office)
Salary: Competitive
Job Type: Permanent, Full Time
About Street Cover
Street Cover was launched in September 2025 and provides 30 day and Annual car insurance for delivery drivers (such as Uber Eats and Deliveroo drivers). Backed by one of the UK's most successful insurance groups, Street Cover combines the agility of a startup with the scale, expertise and resources of an established market leader. We're already making an impact in motor insurance, but this is just the beginning. Street Cover has a bold ambition: to become the UK's leading provider of insurance solutions for delivery drivers and riders.
We're looking for an exceptional Head of Street Cover to lead the next stage of growth. This is a unique opportunity to take ownership of an insurtech business, define its strategy, shape its future product roadmap, and build something genuinely market-leading.
Why Join Us?
This is an opportunity to lead a business, shape its future, launch innovative products, enter new markets, build strategic partnerships, and create the market-leading insurance proposition for the gig economy. If you're excited by high-growth businesses, technology-led innovation, and solving customer problems in new ways, we'd love to hear from you.
What You'll Be Doing
As Head of Street Cover, you'll have full accountability for the business and play a pivotal role in driving its growth. You'll:
- Define and lead Street Cover's strategy, growth plans, brand and customer proposition
- Own the Street Cover P&L and deliver commercial performance
- Identify and execute opportunities to rapidly scale the business
- Translate strategic goals into actionable plans and measurable outcomes
- Lead day-to-day operations and ensure successful delivery
- Partner closely with our dedicated technology squad to develop innovative customer solutions
- Use data and insight to drive decision-making, prioritisation and growth
- Build strong relationships across the wider Group to maximise opportunities and accelerate delivery
- Act as the voice of the customer, ensuring we deeply understand the needs of delivery drivers and riders
Why This Role Is Exciting
Street Cover has significant growth opportunities including:
- New products including Motorcycle, Scooter and Van Insurance
- Flexible cover durations and app-based top-up solutions
- Telematics-led products that better align pricing to actual usage and risk
- Partnerships and integrations with leading delivery platforms such as Deliveroo, Uber Eats and Just Eat
- Expansion into Ireland and wider international markets
- Development of adjacent products including income protection, loss of earnings cover and vehicle finance solutions
What We're Looking For:
We're less interested in industry tenure and more interested in exceptional people who can build, lead and grow businesses. You'll likely have:
- 5-10+ years' experience in strategy, consulting, commercial leadership, venture building, insurtech, fintech or a high-growth environment
- A proven track record of managing multiple priorities and delivering results
- Strong strategic thinking combined with a hands-on execution mindset
- Exceptional analytical and problem-solving skills
- The ability to identify growth opportunities
- Experience working with product and technology teams
- Outstanding stakeholder management and influencing skills
- The energy, drive and ambition to build something special
Particularly Relevant Backgrounds:
- Strategy Consulting (McKinsey, Bain, BCG, Oliver Wyman, Strategy&, OC&C, Kearney or similar)
- Insurtech or Fintech
- Marketplace businesses
- Mobility or transport technology
- Digital scale-ups or Venture-backed businesses
Why Acorn Insurance?
With over 40 years of experience, Acorn Insurance is a specialist provider dedicated to helping individuals secure motor insurance across the UK. We proudly serve more than 50,000 customers. The Acorn Group has been recognised as a Great Place to Work for 2024/5.
Some of the 'your tomorrow' benefits you will receive include:
- Wellbeing: Enhanced Annual Leave entitlement starting at 31 days and potentially increasing to 35 days per year depending on grade & length of service (including bank holidays)
- Enhanced paternity pay and 16 weeks full maternity pay.
- Colleague Assistance programme offering wellbeing services such as: 6 Free Counselling sessions per year, Unlimited access to a telephone councillor 24/7, Access to a free 4-week programme of cognitive behavioural therapy (CBT) with a trained therapist mentor.
- Network of internal qualified mental health first aiders are available to provide support to colleagues.
- Financial: A core level of life assurance with the option to increase cover via salary sacrifice and add your spouse/partner.
- Ability to access your earnings before payday via Dayforce Wallet.
- Refer a friend scheme
- Access to a flexible benefits platform
- Ability to give back. You can opt into donating money to charity to climate positive organisations directly from your salary.
Reward, Recognition and Culture:
- Long Service Awards
- A reward and recognition hub
- Consistent and engaging company events
- Budgets for department leaders to use for social and engagement events.
All roles are subject to DBS and Financial checks, any offer made will be conditional until checks are completed to a satisfactory standard. Due to the length of training and complexity of the role, we can only accept applications from candidates who have at least one year remaining on their (Graduate/ Post study work) visa. Unfortunately, we are unable to provide visa sponsorships.
At Acorn, we are committed to creating an inclusive and supportive work environment. Whether it's modifying equipment, adjusting working hours, or providing additional support, we aim to ensure all employees can perform at their best. If you require any reasonable adjustments, please let us know during the application or interview process, and we will work with you to ensure your needs are met.
Please click on the APPLY button to send your CV and Cover Letter for this role.
Insurance Divisional Manager - Head of Street Cover in Slough employer: Acorn Insurance
At Acorn, we pride ourselves on being an exceptional employer, offering a vibrant work culture in the heart of Liverpool that prioritises employee well-being and growth. With generous benefits such as up to 35 days' holiday, flexible working options, and comprehensive mental health support, we empower our team to thrive both personally and professionally. Join us to make a meaningful impact in the insurance industry while enjoying a supportive environment that champions career progression and inclusivity.
StudySmarter Expert Advice🤫
We think this is how you could land Insurance Divisional Manager - Head of Street Cover in Slough
✨Dive Into Industry Networking Events
Get your foot in the door by attending insurance industry events and conferences. Not only will you learn about the latest trends, but you'll also meet potential employers and industry peers. Check out local chapters of professional bodies like the Chartered Insurance Institute for valuable meetups.
✨Use LinkedIn to Your Advantage
Don’t underestimate the power of LinkedIn in the insurance world. Engage with industry content, join relevant groups, and connect with professionals at companies you admire (like Acorn Insurance). A thoughtful message explaining your interest can really make a difference!
✨Look Out for Graduate Schemes
Many firms in insurance have structured graduate programmes. Keep an eye on application windows and utilise your university's career services for insider tips. These schemes are designed to develop talent and often lead to permanent roles after your initial training.
✨Leverage Your Current Connections
Got friends or family in the industry? Now’s the time to reach out! Personal referrals can give you a head start, so let them know you're on the lookout for full-time opportunities at places like Acorn Insurance. Don’t shy away from asking for a coffee chat; you never know what doors it might open!
We think you need these skills to ace Insurance Divisional Manager - Head of Street Cover in Slough
Some tips for your application 🫡
Highlight Your Analytical Skills:In insurance, we love a candidate who can crunch numbers and analyse data effectively. When crafting your CV, make sure to showcase any relevant coursework or experiences that highlight your analytical abilities, especially if you’ve tackled risk assessment or financial modelling.
Showcase Industry Knowledge:Don’t be shy about your knowledge of the insurance sector! We want to see that you've done your homework on current trends, regulations, and challenges in the industry. Mention any relevant projects or studies you’ve completed that demonstrate your understanding of the field in your cover letter.
Craft a Compelling Cover Letter:Your cover letter should tell us why you’re passionate about insurance. Share any personal experiences or what drew you into this profession. We’re looking for enthusiasm and a clear motivation for why you want to be part of our team at Acorn Insurance.
Tailor Your CV for the Role:Don't just send a generic CV! Focus on tailoring it specifically for the insurance role at Acorn Insurance. Highlight relevant skills such as risk management, customer service experience, or any certifications you've earned in the industry to make your application stand out.
How to prepare for a job interview at Acorn Insurance
✨Know Your Numbers: Insurance Fundamentals
Brush up on your understanding of key insurance concepts, like underwriting principles and risk assessment. Expect the interviewer at Acorn Insurance to throw some technical questions your way, so be ready to demonstrate your grasp of these essentials.
✨Showcase Your Analytical Side
In the insurance world, it's all about data. Prepare to discuss any analytical tools or methodologies you've used in past experiences. If you have a portfolio of projects where you've tackled complex data, bring that along to impress the team!
✨Prepare for Behavioural Questions
As a full-timer at Acorn Insurance, they'll want to know how you handle real-life scenarios, not just theory. Think about challenges you've faced in teamwork or customer service, and how those experiences can relate to a career in insurance.
✨Know the Company Culture Inside Out
Understanding Acorn Insurance's values and workplace culture is essential. Don’t just memorise their mission statement; think about how your personal values align with theirs. This will show your genuine interest in being part of their team long-term.
