Street Cover - Head of Street Cover in Liverpool

Posted Tuesday, 1 September 2026 at 01:00

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.

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.

Job Title: Head of Street Cover

Location: Liverpool City Centre on a Hybrid basis

Full time role, 37.5 hours per week Monday-Friday

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.

• 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.

Why Acorn Insurance?

At Acorn Insurance, we’re proud of our Liverpool roots — and even prouder of how far we’ve come. As part of the Acorn Group, we bring over 40 years of specialist insurance expertise to the table. From humble beginnings, we’ve grown into a national leader, now employing 1,700+ people across the UK and reached a milestone £750 million in total value of insurance policies written in 2024.

We’re growing fast, with new opportunities emerging every week. That growth is largely due to the values we share:

• We run through walls for our customers and each other
• We challenge the status quo
• We succeed when we help those around us succeed
• We decide quickly when the smart thing to do is use our judgement
• 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

Our Commitment to our colleague’s:

These aren’t just words — they’re the principles we live by. And we’re proud to back them up with real action, earning recognition and accreditation from leading organisations that share our commitment to people and growth:

• 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.