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'.
Job CategoryRisk ControlPosition TypeTarget Openings1What 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 know it's tough, but please try to avoid the confidence gap. You don't have to match all the bullet points above to be considered for this role.)
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.
Build the future of digital tech governance with us
We are a technology-driven company redefining the insurance landscape. Here, compliance isn't a modern bottleneck—it’s an active partner in innovation. If you are excited by algorithmic pricing models, scalable e-commerce journeys, and building a compliant-by-design future alongside brilliant tech, product, and data talent, we want to hear from you.
Ready to make an impact? Apply today to lead our compliance team into the next era.
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
Ready to join us and drive our success as a high-performing team? Apply today.
Employment PracticesSimply 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.
Skills Required
- Proven experience modernising compliance functions within regulated UK financial services
- Strong knowledge of FCA frameworks, including Consumer Duty, ICOBS, and PROD 4
- Relevant senior compliance or legal qualification, such as ICA, CISI, or LLM
- Experience with digital distribution and e-commerce
- Experience overseeing algorithmic or AI pricing governance
- Ability to communicate complex regulatory requirements in clear commercial language
- Ability to build trusted relationships with executives, boards, regulators, and cross-functional teams
What the Team is Saying
Simply Business Compensation & Benefits Highlights
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Leave & Time Off Breadth — Policies include a large PTO allotment with sick days, company and floating holidays, paid volunteer time, and formal sabbaticals after long service. Feedback suggests this combination is a standout element of the package.
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Retirement Support — Offerings include a 401(k) through Fidelity with employer match, plus performance bonus eligibility and protections like disability and life insurance. These features are consistently positioned as strengthening employees’ long-term financial security.
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Parental & Family Support — Materials describe a generous parental leave program with fully paid primary-caregiver leave, flexible shared parental options, and adoption assistance. Company-sponsored family events and childcare-related perks further reinforce family support.
Simply Business Insights
What We Do
Simply Business is the leading digital insurance marketplace dedicated to the success of small businesses. Our mission is to take the hassle out of buying insurance by offering simplicity, choice, and value to business owners. We connect our customers with top-rated insurers and policy recommendations tailored to their specific business needs and budget. We have nearly 20 years of experience supporting small businesses, with over 1 million customers worldwide. Founded in the U.K. in 2005, Simply Business revolutionized how small businesses find insurance, making it accessible and affordable. We then saw a similar need in the United States. So in 2017, we launched Simply Business in the U.S.. Today, our team sits across offices in Boston in the U.S., as well as in London and Northampton in the U.K., showcasing our innovation at scale and dedication to serving the backbone of our economies. Simply Business is more than our name. It’s how we approach small business insurance.
Why Work With Us
Here at Simply Business we have five core values that we uphold in everything that we do: Learning, Empowerment, Authenticity, Pioneering, and Simplicity. Utilizing these values and embedding them into our culture makes SB a unique and great place to work, a place where every person is valued, a place where we get things done and have fun doing so.
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Simply Business Teams
Simply Business Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
We offer our SBers more choice and greater flexibility to work in a way that’s best for their particular job, their teams, and their lives. We ask our employees to come to our hubs 8X a month.
