At a Glance
- Tasks: Lead the strategy and growth of an innovative insurtech business for delivery drivers.
- Company: Join a fast-growing startup backed by a leading insurance group.
- Benefits: Enjoy up to 35 days holiday, mental health support, and flexible working options.
- Other info: Be part of a supportive culture focused on career progression and inclusivity.
- Why this job: Shape the future of insurance and make a real impact in the gig economy.
- Qualifications: 5-10+ years in strategy or commercial leadership with a hands-on approach.
The predicted salary is between 75600 - 92400 £ per year.
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). Street Cover has a bold ambition: to become the UK's leading provider of insurance solutions for delivery drivers and riders. 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.
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. 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:
- 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 across multiple workstreams
- 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 ahead. This role offers the chance to shape and deliver these opportunities from the ground up. 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
- Commercial instinct and an 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
Why Join Us:
This is not a traditional insurance leadership role. It's 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 looking for autonomy, pace, impact and the chance to build something unique, we'd love to hear from you.
Benefits:
- A maximum of 35 days’ holiday (depending on role and tenure) including bank holidays, with additional buy/sell options
- 24/7 mental health support & free counselling available
- Grow with us: Through career fairs, leadership programs, and learning on the go!
- Flexible benefits, including early access to salary via our internal platform
- Hybrid working options to support work-life balance and individual needs
- Recognition awards, social events & more
Our Commitment to our Colleagues:
- Mindful Employer – championing mental health and wellbeing
- Disability Confident Level 1 & 2 – creating accessible, inclusive opportunities
- Menopause Friendly accredited – supporting every stage of life
- Armed Forces Covenant signatory – honouring those who serve
- Armed Forces Defence employer recognition scheme – Supporting those who serve
- Great Places to Work 2024/25 – fostering an engaging and positive workplace culture
- Best Place to Work for Development – proud to be investing in people’s future
- Best Place to Work for Women – breaking down barriers to women's career progression
If you’re looking for a company with a strong culture, real career progression, and a people-first approach — all rooted in the heart of Liverpool — Grow with Acorn.
A Few Things to Know Before You Apply:
We’re really excited that you’re considering joining Acorn! To help everything go smoothly, here are a couple of things to keep in mind: If your application is successful, we will commence relevant employment checks prior to you commencing employment with us. These will include a standard criminal record check and an insolvency register check.
Visa Requirements:
Because our training is quite comprehensive, we can only consider applicants who have at least one year remaining on their Graduate or Post-Study Work visa. At the moment, we’re not able to offer visa sponsorship.
We’re Here to Support You:
We’re committed to creating an inclusive, supportive workplace where everyone can flourish. If you need any adjustments at all, just let us know. Whether it’s flexible hours, adapted equipment, or a bit of extra support, we’ll work with you to make sure you can do your best work.
Head of Street Cover in Liverpool employer: Acorn Group
Acorn Group is an excellent employer, offering a dynamic work environment in the heart of Liverpool City Centre. With a strong focus on employee growth and development, we provide hybrid working options, competitive salaries, and the chance to make a real impact through data-driven insights. Join us to be part of a collaborative culture that values innovation and engagement at all levels.
StudySmarter Expert Advice🤫
We think this is how you could land Head of Street Cover in Liverpool
✨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 Group). 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 Group. 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 Head of Street Cover in Liverpool
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 Group.
Tailor Your CV for the Role:Don't just send a generic CV! Focus on tailoring it specifically for the insurance role at Acorn Group. 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 Group
✨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 Group 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 Group, 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 Group'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.
