Job Summary
We are seeking a new Head of Sales to join our team here at Square Health!
About Square Health
Square Health is a leading digital healthcare provider, delivering innovative clinical services and technology platforms to insurers, employers, and consumers. Our ecosystem spans mobile and web applications, enterprise portals, APIs, and integrated clinical services enabling scalable, personalised healthcare journeys.
We work with major corporate clients and partners to deliver modern, accessible healthcare solutions, combining clinical expertise with advanced technology. At Square Health, you’ll be part of a collaborative, ambitious team focused on improving health outcomes through digital transformation.
Job Purpose: The Head of Sales – Workplace Health will be responsible for leading the workplace health sales function to grow our PMO and Integrated Occupational Health products (https://www.squarehealth.com/workplace-health), providing strategic direction, commercial leadership and day-to-day management for a team of Workplace Health Sales Consultants. The role will drive new business growth through multiple channels (UK Intermediaries, Employee Benefit Consultants (EBCs), Direct Corporate sales), pipeline quality, conversion performance and revenue delivery across target employer markets through a consultative, professional and insight-led sales approach. Working closely with the Workplace Health Director, marketing, clinical, operational and senior stakeholders, the role will shape sales strategy, support lead generation, oversee tender and proposal activity, coach the sales consultants/executives, manage key prospects and ensure opportunities are converted into well-scoped, commercially robust contracts with a smooth handover to operational teams. The role will also be accountable for sales forecasting, CRM discipline, performance management, market insight and the continuous improvement of sales processes, ensuring the team consistently represents the organisation with professionalism, integrity and strong sector knowledge.
Main Accountabilities:
1. Sales strategy and leadership. Develop and lead the workplace health sales strategy, translating business objectives into clear sales priorities, target markets, activity plans and measurable performance expectations for the sales team.
2. Team management and coaching. Lead, manage and develop Workplace Health Sales Consultants/Executives, providing coaching, performance management, deal support and regular feedback to improve capability, confidence, conversion and consistency.
3. Pipeline performance and forecasting. Oversee the sales pipeline, ensuring accurate CRM use, disciplined opportunity management, robust forecasting and timely reporting of activity, conversion, revenue, margin and risks to target delivery.
4. Lead generation and prospecting oversight. Work with marketing and internal stakeholders to shape lead generation campaigns, events, referrals, market outreach and direct prospecting activity, ensuring the team builds and maintains a high-quality pipeline across target employer sectors.
5. Key prospect and client engagement including Intermediaries, EBCs and Corporates. Support and, where appropriate, directly lead engagement with Intermediaries, EBCs and Corporate strategic prospects, senior buyers, procurement teams and intermediary partners, ensuring client needs, business drivers and workforce health challenges are understood and addressed.
6. Solution positioning and commercial governance. Guide the team in positioning workplace health and occupational health solutions clearly and persuasively, ensuring proposals, pricing, service scope and commercial recommendations are aligned to client needs, margin expectations and internal governance.
7. Tender, bid and presentation leadership. Lead the sales contribution to formal tenders, bids and procurement processes, coordinating internal input and ensuring submissions and presentations are accurate, compelling, commercially robust and professionally delivered.
8. Contracting and handover. Oversee commercial negotiation, contracting, internal approvals and service handover activity, ensuring signed agreements are clear, compliant, deliverable and transitioned effectively to operational teams.
9. Cross-sell and up-sell leadership. Identify, prioritise and guide appropriate cross-sell and up-sell opportunities across workplace health and wider service propositions, ensuring recommendations remain relevant, ethical and commercially sound.
10. Market insight and competitor awareness. Maintain strong awareness of the workplace health, employee wellbeing and occupational health market, including buyer needs, competitor activity, regulatory context, intermediary trends and opportunities for proposition development.
11. Internal collaboration and continuous improvement. Work collaboratively with marketing, clinical, operational, finance and senior stakeholders to improve sales processes, strengthen proposition quality, support onboarding and ensure feedback from prospects and clients informs service development.
Other Duties:
- Comply with any reasonable ad-hoc work requests from the Director and/or Senior Management.
- Undertake any training deemed appropriate by the Director and/or Senior Management, including maintaining up-to-date knowledge of relevant UK workplace health legislation, regulatory expectations and market developments.
- Comply with and promote all Company Policies.
- Comply with the Company’s Information Security Policy and risk and all other Company Policies applicable to the role.
Skills & Attributes Required:
- Proven senior sales leadership experience within employee health, occupational health, wellbeing, healthcare, insurance, employee benefits or a related B2B service environment.
- Good working experience and relationships with the major UK Intermediaries would be an advantage.
- Demonstrable experience leading, coaching and performance-managing sales consultants or business development teams to deliver revenue, margin, pipeline and conversion objectives.
- Strong understanding of employee health needs, occupational health services and the challenges employers face in supporting workforce wellbeing, absence management, health risk and organisational resilience.
- Good understanding of UK workplace health legislation, employer duties and relevant regulatory considerations, with a commitment to keeping this knowledge current through ongoing learning and market engagement.
- Strong commercial acumen, including experience of pricing, margin management, contract negotiation, sales forecasting and governance of complex proposals.
- Excellent consultative selling capability, with the confidence to engage senior buyers, procurement teams, intermediaries and internal stakeholders.
- Experience leading formal tenders, bids and procurement processes, including coordinating multi-disciplinary input and delivering compelling client-facing presentations.
- Confident using CRM, sales reporting, marketing insight and performance dashboards to manage activity, monitor conversion and inform strategic business development decisions.
- Comfortable using AI tools such as ChatGPT, Copilot or similar to enhance productivity, communication, insight generation and sales team performance.
- Strong written and verbal communication skills, including the ability to produce clear proposals, executive-level communications, sales reporting and internal briefing materials.
- Ability to work collaboratively with marketing, clinical, operational, finance and senior stakeholders to support lead generation, client conversion, onboarding and service development.
- High attention to detail and a professional approach to handling client information, commercial documentation, contractual requirements and confidential business information.
Behaviours Required:
- Demonstrates honesty, integrity and professionalism in all prospect, client, intermediary and internal interactions.
- Provides visible, positive and accountable leadership for the sales team, setting clear expectations and supporting people to perform at their best.
- Commercially driven while remaining client-focused, consultative and values-led.
- Strategic and data-driven, using insight, pipeline information and market intelligence to guide priorities and decision-making.
- Collaborative and influential, able to bring colleagues together around shared commercial goals and client outcomes.
- Growth-minded, resilient and proactive in creating opportunities, overcoming barriers and improving sales performance.
- Comfortable with ambiguity, changing priorities and a fast-moving commercial environment.
- Values diversity and difference and will consider the most effective way to promote equality of opportunity and good working relationships in employment and service delivery.
Benefits:
- Highly Competitive Salary
- Flexible work arrangements - A mix of remote working & visits to our office based in Windsor when required
- 25 Days Holiday
- Company pension scheme
- 24/7 Online GP
- Private Prescription Service
- Best Doctors – second opinion
- Mental Health Support – this is in addition to the support line already on offer
- Wellbeing Services – access to nutrition planning, fitness and online health check
If this exciting opportunity is of interest to you and you would like to find out more, then please apply today!
Ability to commute/relocate:
- Windsor SL4 1AT: reliably commute or plan to relocate before starting work (required)
Experience:
- Senior Sales Leadership: 5 years (required)
Work Location: Hybrid remote in Windsor SL4 1AT
