Enterprise Account Executive

Location: Remote (UK)

Type: Full-Time

Salary: Up to £180k OTE Uncapped (£80k base x 2 uncapped)

Who We Are

At Toothfairy, we’re rebuilding dental care for the modern workforce. We’re a CQC-regulated digital dental clinic that gives employees instant access to real dentists, prescriptions, triage, and preventative care, all through a single app. No waiting lists. No expensive emergencies that could have been avoided. Employers, insurers, and brokers use Toothfairy to solve a problem that traditional benefits don’t touch: dental access. We reduce dental-related absence, prevent issues escalating into claims, and remove a surprisingly large source of distraction and downtime across workforces. We already support 1,000+ organisations and over 1 million employees, and we’re now scaling a serious enterprise B2B engine targeting large employers, complex workforces, and major broker networks.

This is not a “nice-to-have wellbeing perk”. It’s a clinically regulated service solving a broken UK system, with real operational and financial impact.

About the Role

As an Enterprise Account Executive, reporting directly to the Chief Revenue Officer, you’ll own high-value enterprise opportunities end-to-end. You’ll sell into HR, Reward, Benefits, Wellbeing leaders at large UK employers. These are multi-stakeholder, consultative sales, often involving brokers, insurers, and complex internal decision-making. This role is for someone who wants real ownership, a big commercial number, and the chance to help define how a category is sold, not just follow a playbook. You will use AI and data as a competitive advantage throughout the sales cycle, not to replace human selling, but to sharpen insight, prioritisation, and decision-making in complex deals.

What You’ll Be Doing

• Full Ownership of the Enterprise Sales Cycle
• Own deals from first conversation through to close, with full accountability for pipeline quality, velocity, and conversion.
• Run complex, multi-threaded enterprise sales cycles, typically £100k–£250k+ ARR.
• Deliver predictable revenue against a £1m+ annual quota.
• Use AI-assisted analysis to identify deal risk, stakeholder gaps, next-best actions, and prospect engagement across your pipeline.

• Prospecting and Relationship Building
• Self-source pipeline through intelligent outbound, alongside inbound leads generated by our BDR and Demand teams.
• Build senior relationships across HR, Reward, Benefits, Wellbeing, and Exec stakeholders.
• Navigate organisations where the buyer, budget holder, and sponsor are not the same person.

• Consultative & Strategic Selling
• Use SPICED to manage deal complexity, risk, and forecast accuracy.
• Sell outcomes, not features: absence reduction, productivity, prevention, claims deflection, and employee experience.
• Confidently challenge “we already have Insurance / cash plans” thinking with a differentiated, prevention-led narrative.
• Use AI to tailor commercial narratives to different stakeholder concerns within the same account.

• Broker & Partner Engagement
• Work closely with employee benefits brokers and consultants as part of the sales motion.
• Co-sell, enable, and navigate broker-led deals without losing deal control.

• HubSpot & Commercial Discipline
• Maintain a clean, honest, and well-managed pipeline in HubSpot.
• Use data, not vibes, to forecast, prioritise, and course-correct.
• Collaborate closely with RevOps to improve processes, reporting, and GTM efficiency.

• Market Feedback & GTM Evolution
• Feed real-world buyer insight back into Product, Marketing, and Leadership.
• Help shape Toothfairy’s enterprise messaging, pricing, packaging, and sales narrative as we scale.
• Contribute insight on how AI can be applied across the sales motion to improve win rates, not just volume.

What You’ll Bring

• Experience
• 5-7 years in enterprise B2B SaaS or services sales, ideally in HR tech, benefits, wellbeing, or adjacent spaces.
• Startup experience (Seed–Series B) where ambiguity, pace, and ownership are the norm.
• Proven and defensible track record closing £200k+ ARR enterprise deals and carrying £1m+ quotas.
• Strong experience selling to HR / People / Reward buyers and working alongside brokers.
• Expert-level HubSpot user across pipeline management, reporting, workflows, and forecasting.
• Experience working with SDRs/BDRs to generate and progress pipeline.
• Hands-on experience using AI tools to enhance deal strategy, account insight, forecasting, or stakeholder management in complex sales cycles.

• Sales Craft
• Fluent in SPICED for complex enterprise deals.
• Strong consultative seller with Challenger instincts.
• Comfortable running senior, commercial conversations without hiding behind slides.

• Skills
• Clear, confident communicator who can simplify complex ideas.
• Strong numerical and commercial judgement. You understand ROI, cost drivers, and business cases.
• Excellent relationship-builder at C-suite and senior leadership level.

• Mindset
• Highly autonomous. You do not need hand-holding and you actively dislike micromanagement.
• Creative and commercially curious. You test, iterate, and improve rather than run vanilla plays.
• Resilient and coachable. You give and receive feedback without ego.
• Motivated by building something meaningful, not just hitting a number.
• AI-native but sceptical: you use AI where it creates leverage, not because it’s fashionable.

Why Join Toothfairy?

• A Real Problem, Properly Solved: Dental access in the UK is broken. Toothfairy fixes it. Employers care. Employees care. Selling it feels good.
• Enterprise GTM at the Right Moment: The engine is built, demand is real, and now it’s about scale. You’ll shape how we win big deals.
• High Impact, High Trust Environment: Smart people, low politics, no passengers.
• Serious Earning Potential: Uncapped commission, meaningful equity, and a product that actually converts when sold well.
• Remote-First, Outcome-Driven: Flexibility without chaos. Autonomy without ambiguity.
• A Sales Role Built for the AI Era: You’ll be expected to use modern AI tools to sell better, not harder, as we scale a category-defining GTM motion.