Head of Sales - Growth & Retention

At Simplyhealth, we’re more than just a company; we’re a certified B Corp with a 150-year heritage of improving access to healthcare across the UK. Today, we support around 2.5 million members through affordable health and dental plans, helping people access the care they need when they need it most.

We’re looking for a Head of Sales (Growth & Retention) to take on one of the most commercially significant roles in our Health Plan business. This is a senior, high‑impact role, accountable for protecting and growing a £126m book of business, strengthening retention, and unlocking meaningful expansion across our largest and most complex B2B clients.

Reporting to the Sales & Marketing Director, you will lead the growth and retention strategy for Simplyhealth’s Health Plan line of business, with full accountability for commercial performance across direct, broker and digital channels.

This role sits at the heart of the business and carries executive ownership of several marquee employer clients, including some of the UK’s best‑known brands. You will be responsible for retaining and growing relationships of real scale, navigating complex stakeholder environments, and delivering value in the face of ongoing economic and market headwinds.

You’ll lead a team of around eight experienced sales and account management professionals, setting clear direction, building strong commercial discipline and ensuring a relentless focus on customer value, retention and sustainable growth. Success in this role comes from deep client understanding, confident senior‑level engagement, and the ability to convert insight into action.

Working within a product‑led, matrix organisation, you’ll collaborate closely with Product, Tech, Marketing, Pricing, Operations and Sales & Marketing Operations to ensure commercial strategies are aligned with product evolution, digital experience and long‑term customer outcomes.

This is a role for a commercially astute leader who enjoys ownership, complexity and accountability - and who wants to make a genuine impact on access to healthcare in the UK.

This role will suit a seasoned commercial leader who thrives in high‑value B2B environments. You’ll need to bring:

• Senior‑level experience in sales growth, sales retention, account management or client leadership roles.
• A proven track record of managing and growing large, complex employer or broker‑led accounts.
• Background in healthcare, private medical insurance (PMI), cash plans, insurance or employee benefits, with strong understanding of broker and client dynamics.
• Confidence operating in challenging macro‑economic conditions, balancing retention with expansion.
• Strong commercial instincts, underpinned by data, insight and disciplined forecasting.
• Experience leading, motivating and developing high‑performing teams.
• The presence and credibility to operate at executive level with clients and internal stakeholders.

Above all, you’ll care deeply about customer outcomes, while fully embracing the commercial responsibility that comes with leading one of Simplyhealth’s most important growth engines.

In Return, We Offer

• Competitive base salary (to be discussed at screening call).
• Significant commission opportunity (c.40% commission, balanced across growth and retention).
• Car allowance.
• 36 days’ holiday (including bank holidays), with buy/sell options.
• Flexible pension scheme.
• Annual company‑funded benefits allowance.
• Simplyhealth core product (Health Cash Plan or Dental Plan).
• Life assurance.
• A senior leadership role with real influence, scale and purpose.

We’re committed to a fair, inclusive and transparent recruitment process. The journey will include:

• An initial screening call with our Head of People Operations
• A first‑stage interview with the Sales & Marketing Director and Head of HR Partnering
• Psychometric and verbal numerical test
• A final presentation to the Sales & Marketing Director and other key executive and business leadership stakeholders

All offers are subject to standard pre‑employment checks.

If you’re an experienced, commercially driven leader who enjoys owning growth, building trusted client relationships and delivering results at scale - we’d love to hear from you!