Head of Compliance

We insure small businesses and enable big dreams – not just for our customers, but for our people and communities too. With over 1,000,000 active insurance policies, we protect builders, bakers, landlords and more than 1,200 other trades. We’re a technology company as well as one that sells insurance. That means we build, we fail, we learn and we improve. Through our global social impact strategy, called 'The Big Dreams Project’, we're working to help 10,000 small businesses start or grow by 2030.

What Is the Opportunity?

Compliance isn’t about ticking boxes or standing in the way of progress. At Simply Business, it’s about enabling high-speed commercial growth, pioneering digital insurance journeys, and serving as a trusted partner to fuel responsible innovation while keeping our enterprise robust and reliable as we scale. As our Head of Compliance, you’ll be a strategic, forward-thinking leader overseeing our entire UK compliance architecture. Reporting directly to the General Counsel, you’ll define and embed proactive regulatory frameworks that support ambitious digital tech, algorithmic pricing, and customer-first products—proving that strong governance and rapid business growth can go hand in hand.

As one of our Head of Compliance, you’ll:

• Lead, develop, and inspire a high-performing team across Compliance Business Partnering, Monitoring, and Governance.
• Own and execute our multi-year UK compliance strategy, ensuring regulatory expectations and Consumer Duty are embedded into our company DNA.
• Act as our primary contact for regulatory authorities, holding key Senior Management Functions (SMF16 and SMF17).
• Architect and continuously optimise proactive, risk-based compliance frameworks, oversight policies, and operational controls.
• Partner closely with executive peers across Tech, Product, Finance, and Commercial to build compliant-by-design, frictionless operations.
• Deliver high-impact, actionable insights and Management Information (MI) directly to the Board and Executive Leadership.

We’re looking for someone who is:

• An experienced regulatory leader with a proven record of modernising compliance functions within regulated UK financial services.
• Deeply knowledgeable about FCA frameworks (Consumer Duty, ICOBS, PROD 4), backed by a relevant senior qualification (e.g., ICA, CISI, LLM).
• Experienced in digital distribution, e-commerce, and algorithmic or AI pricing governance.
• An exceptional, plain-English communicator who can translate complex regulatory mandates into clear, commercial guidance.
• Highly collaborative, with the strategic gravitas to build strong, trusted relationships across executives, boards, and regulators.
• Agile, resilient, and energised by solving complex challenges in a fast-paced environment.

We encourage people of all different backgrounds and identities to apply. We are committed to maintaining an inclusive, supportive place for you to be you and do your very best work.

What are the benefits of working at Simply Business:

• We offer a great work-life balance where workloads are manageable and everyone has the flexibility to work hybrid.
• On top of the 25 days annual leave (plus bank holidays), we offer the option to buy five more days of holiday with your flexible benefits.
• Our flexible parental leave allows you to approach an important time how you want - with six months full pay to the primary caregiver and four weeks full pay if you're the secondary caregiver.
• Our life event leave is an extra days leave every two years for those big moments in your life like moving house or your birthday.
• Long-serving employees get a two week paid sabbatical after five years of service, then four weeks off after ten years of service.
• Private medical insurance through BUPA, that covers any pre-existing condition is a core benefit. Plus a health cash plan that covers your everyday medical expenses.
• We offer a competitive salary based on your experience and the current market. Plus the potential to earn an annual bonus based on performance.
• Access to tools to support your personal development on our dedicated learning platform, as well as support for your mental health with access to counselling.
• We match what you put into your pension up to five per cent. And pass on a tax-free sum that's four times your basic salary with our life assurance policy, with the option to increase it to ten times through our flexible benefit scheme.
• Our salary sacrifice car scheme gives you the option to buy a brand new, fully insured, and maintained car for a convenient fixed monthly amount taken from your gross salary (after 6 months service).
• Our flexible benefits scheme gives you an allocated amount to use each year on benefits like critical illness cover, dental insurance, travel insurance, or a gym membership.

Ready to join us and drive our success as a high-performing team? Apply today.