Job Title: Enterprise Account Executive
Location: Remote (UK)
Type: Full-Time
Salary: Up to £160k 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 \"two weeks on Tuesday at 11am\". 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 cross 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.
