Insurance Divisional Manager – Head of Street Cover

Job Title: Head of Street Cover

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.