Head of Street Cover (Insurtech)

Location: Hybrid with office days in Liverpool; some office days may be worked from the London office.

Company

Acorn Insurance is a UK motor insurance provider with more than 40 years of experience and over 50,000 customers, backed by an established insurance group.

What you will do

• Define and lead Street Cover’s strategy, growth plans, brand, and customer proposition.
• Own the business P&L and deliver commercial performance.
• Identify and execute opportunities to rapidly scale the delivery-driver insurance business.
• Lead day-to-day operations and coordinate delivery across multiple workstreams.
• Partner with the technology squad to develop innovative customer solutions and shape the product roadmap.
• Build relationships across the wider Group, delivery platforms, and other strategic partners.

Requirements

• 5–10+ years of experience in strategy, consulting, commercial leadership, venture building, insurtech, fintech, or a high-growth environment.
• Proven ability to manage multiple priorities and deliver measurable results.
• Strong strategic thinking combined with a hands-on execution mindset.
• Exceptional analytical, problem-solving, commercial, stakeholder-management, and influencing skills.
• Experience working with product and technology teams.
• At least one year remaining on a Graduate or Post-study work visa is required; visa sponsorship is not available.

Nice to have

• Background in strategy consulting, insurtech, fintech, marketplace businesses, mobility or transport technology, digital scale-ups, or venture-backed businesses.

Culture & Benefits

• Autonomy, pace, and the opportunity to build a market-leading insurance proposition for the gig economy.
• Enhanced annual leave of 31–35 days, including bank holidays.
• Enhanced paternity pay and 16 weeks of full maternity pay.
• Wellbeing support, including counselling, cognitive behavioural therapy, and mental health first aiders.
• Life assurance, flexible benefits, salary access before payday, and colleague referral rewards.
• Inclusive workplace with reasonable-adjustment support, company events, and recognition programmes.

Hiring process

• Offers are conditional on satisfactory DBS and financial checks.