Account Executive

Location: Remote (UK)

Type: Full-Time

About Toothfairy

At Toothfairy, we're building the category leader in dental healthcare access. The UK dental system is broken. Millions of employees struggle to access timely care, employers lose productivity every day to preventable dental issues, and most traditional benefits only step in after the problem has already become expensive. We've built something different. Toothfairy is a CQC-regulated digital dental clinic that gives employees on-demand access to qualified dentists, prescriptions, treatment guidance and preventative care through a single app. Already trusted by more than 2,000 organisations and over 1 million employees, we're now scaling our enterprise business across major employers, insurers and broker networks.

For the right salesperson, this is an opportunity to join early, help define a category, and sell a genuinely differentiated healthcare solution into a market that is only becoming more relevant.

About the Role

As an Account Executive, reporting directly to the Chief Revenue Officer, you'll own opportunities from first conversation through to close. You'll work with HR, Reward, Benefits and Wellbeing leaders across SME, Corporate and Mid-market organisations, helping them solve a workforce challenge that is becoming increasingly difficult to ignore. Success in this role isn't about navigating endless procurement cycles or managing huge account teams. It's about asking great questions, building a compelling business case, running an effective sales process and consistently creating momentum.

We're looking for someone who wants genuine ownership, a meaningful revenue target, and the opportunity to help shape a growing category rather than simply inherit an established playbook. You'll also be expected to embrace AI, data and modern sales technology to improve prospecting, preparation, prioritisation and deal execution, allowing you to focus more time on building relationships and winning business.

What You'll Be Doing

• Full Ownership of the Sales Cycle
  • Own opportunities from first conversation through to close, with full accountability for pipeline quality, velocity and conversion.
  • Deliver predictable revenue against an annual quota of £700k+ in ARR.
  • Run disciplined sales processes, identifying deal risk early and creating momentum throughout the buying journey.
  • Use AI, automation and data as a competitive advantage to improve prioritisation, preparation and execution.
• Prospecting & Relationship Building
  • Self-source pipeline through intelligent outbound activity, alongside inbound opportunities generated by our BDR and Demand teams.
  • Build relationships with HR, Reward, Benefits, Wellbeing and People leaders across SME, Corporate and Mid-market organisations.
  • Navigate buying processes where the user, sponsor and budget holder are often different stakeholders.
• Consultative Selling
  • Use SPICED to manage opportunities, qualify effectively and improve forecast accuracy.
  • Sell business outcomes, not product features, including absence reduction, productivity, prevention, employee experience and claims deflection.
  • Confidently challenge traditional thinking around dental benefits with a differentiated prevention-led narrative.
• Broker & Partner Engagement
  • Work closely with employee benefits brokers, consultants and strategic partners throughout the sales process.
  • Co-sell effectively while maintaining ownership of deal progression and commercial outcomes.
• Commercial Discipline
  • Maintain a clean, accurate and trustworthy pipeline in HubSpot.
  • Forecast with discipline and use data to prioritise activity and manage performance.
  • Work closely with RevOps to continuously improve process, reporting and GTM effectiveness.
• Market Insight & GTM Development
  • Feed buyer insight back into Product, Marketing and Leadership teams.
  • Help shape messaging, pricing, packaging and sales strategy as Toothfairy scales.
  • Contribute ideas that improve conversion, efficiency and win rates across the commercial organisation.

Mandatory Experience & Skills

• 5+ years' experience in B2B new business sales, ideally within SaaS, employee benefits, healthtech, HR technology, wellbeing, insurance, or related sectors.
• Demonstrable track record of consistently achieving or exceeding quota in a new business closing role.
• Experience carrying a significant new business target, typically £700k+ annually.
• Strong consultative selling skills, with the ability to build business cases, uncover needs, and manage opportunities from discovery through to close.
• Experience selling into varying organisation sizes, engaging stakeholders across HR, Reward, Benefits, People, Operations, or similar functions.
• Comfortable prospecting and generating opportunities alongside marketing and SDR support.
• Strong CRM discipline, including pipeline management, forecasting, reporting, and opportunity planning within HubSpot or a comparable CRM platform.
• Experience operating in high-growth/start-up environments where pace, ownership, and adaptability are expected.
• Commercially minded, highly organised, and comfortable working with data to prioritise activity and improve performance.
• Curious about emerging technologies and able to demonstrate practical use of AI, automation, or sales intelligence tools to improve effectiveness.

Why Join Toothfairy?

• Join at an Inflection Point
  • We've recently secured a $10m Series A investment and are entering the next phase of growth. The foundations are in place, demand is building, and we're now scaling our enterprise business across employers, insurers and broker networks.
• Shape the Future of the GTM Function
  • This isn't a role where you'll inherit a mature sales machine and simply follow a playbook. You'll help define how Toothfairy wins, scales and builds a category in the years ahead.
• Sell a Product That Solves a Real Problem
  • The UK's dental access crisis affects millions of employees and costs employers significant time, productivity and money every year. Buyers understand the problem. Our job is helping them solve it.
• Win with Modern Tools
  • We're investing heavily in sales intelligence, automation and AI to help our team work smarter. You'll have access to a modern GTM stack designed to improve prospecting, preparation, prioritisation and execution.
• Earn Meaningfully from Success
  • You'll receive a competitive salary, uncapped commission, meaningful equity participation and the opportunity to create outsized career progression as the business scales.
• Work with Ambitious People
  • We're building a high-performance culture with high trust, low ego and a strong bias for action. We care about outcomes, not politics.