Job Description

Street Cover (www.streetcover.co.uk) 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.
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.
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 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, 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
This role offers the chance to shape and deliver these opportunities from the ground up.
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
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
Particularly Relevant Backgrounds
Strategy Consulting (McKinsey, Bain, BCG, Oliver Wyman, Strategy&, OC&C, Kearney or similar)
Insurtech
Fintech
Marketplace businesses
Mobility or transport technology
Digital scale-ups
Venture-backed businesses

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.
Location:

• Hybrid with office days in Liverpool
• Option to work some office days from London office
About 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, ensuring they find policies that meet their needs and provide the peace of mind that comes with high-quality cover.
At Acorn Insurance, we offer comprehensive training and continuous in-house coaching. You'll receive in-depth, FCA-regulated industry knowledge and all the tools necessary to grow your career with us.
We celebrate diversity and are committed to fostering a culture where everyone feels respected and valued. As a Disability Confident employer, we ensure our workplace is accessible and inclusive, encouraging our people to bring their best selves to work every day.
The Acorn Group has been recognised as a Great Place to Work for 2024/5.

Why Acorn Insurance?
Acorn Insurance want to give you more than a job, we want to give you a purpose and a career. So, what can we offer you as an employer? 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 offers a suite of 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 with a £250 bonus for every colleague recommended on passing their probation period.
• Access to a flexible benefits platform including an annual flex pot allowance to spend on over 15 benefits of your choice.
• 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 Award paid on 5,10- and 15-years’ service
• A reward and recognition hub to celebrate and reward colleagues and peers.
• Consistent and engaging company events including company awards, competitions and charity fundraisers.
• Budgets for department leaders to use for social and engagement events.

Visit our website to view more of our excellent work benefits!
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.