Head of Compliance

Travelers Canada; Greater London; Hybrid; GBP 120,000 - 160,000; Full time

Benefits offered by this job

25 days annual leave

Bank holidays included

Private medical insurance (BUPA)

Life assurance up to 4x salary

Pension employer match up to 5%

Sabbatical after 5 years

Job summary

Simply Business is seeking a Head of Compliance to lead our UK regulatory strategy and governance. You will oversee a multi-disciplinary team, embed proactive frameworks, and serve as the principal liaison to regulators to support rapid digital growth.

Candidate thrives in a fast-paced, tech-enabled environment and translates complex rules into practical guidance for executives. This role offers hybrid working arrangements and a competitive package.

Qualifications

• 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).
• Experienced in digital distribution, e-commerce, and algorithmic or AI pricing governance.
• Exceptional, plain-English communicator who translates regulatory mandates into clear guidance.
• Highly collaborative with the strategic gravitas to build trusted relationships across executives, boards and regulators.
• Agile, resilient, and energized by solving complex challenges in a fast-paced environment.

Responsibilities

• Lead and inspire a high-performing team across Compliance Business Partnering, Monitoring, and Governance.
• Own and execute multi-year UK compliance strategy with embedded Consumer Duty.
• Act as primary contact for regulatory authorities (SMF16/SMF17).
• Architect and optimise proactive, risk-based compliance frameworks, policies and controls.
• Partner with Tech, Product, Finance, and Commercial to enable compliant-by-design operations.
• Deliver MI and insights directly to the Board and Executive Leadership.

Skills

Regulatory leadership

Regulatory frameworks

Consumer Duty

Digital distribution

AI pricing governance

Stakeholder management

Education

ICA/CISI/LLM

Job description

Who Are We?

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. Why not check out our advert on YouTube: Simply Business TV advert 2024: 'Simply the Best'.

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
• and our 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

Employment Practices

Simply Business is committed to providing equality and opportunities for all employees and candidates considering a career with us. We offer a workplace where colleagues are treated with respect and dignity. We don’t (and won’t) discriminate either directly or indirectly on the grounds of race, colour, religion, belief, political opinion, disability, nationality, ethnic origin, sex, sexual orientation or relationship status at any stage of the hiring process or during the course of your employment.

To explore career opportunities and learn more about Simply Business, check out our US career page or our UK career page. At Simply Business, we insure small businesses and enable big dreams. Not just for our customers, but for our people, our communities and our environment. We believe a world-class company culture is crucial to achieving our business goals as we make insurance more accessible to small business owners. We’re building a better way to buy small business insurance, and we’re using technology to get the job done. That includes developing cutting‑edge data gathering and analysis capabilities; living and breathing testing and experimentation; and harnessing the many benefits of AI and other emerging technologies. We’re a values‑led business. Our people all have a part to play in building a culture that lives these values: learning, empowerment, authenticity, pioneering, and simplicity.