Enterprise Account Executive

Location: Otford

Job Title:

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 "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 work forces.

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 work forces, 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.

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.

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 Insurane / cash plans" thinking with a differentiated, prevention‑led narrative.

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.

Hub Spot & Commercial Discipline

• Maintain a clean, honest, and well‑managed pipeline in Hub Spot.
• Use data, not vibes, to forecast, prioritise, and course‑correct.
• Collaborate closely with Rev Ops 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.

What You’ll Bring Experience

• 5+ 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 Hub Spot user across pipeline management, reporting, workflows, and forecasting.
• Experience working with SDRs / BDRs to generate and progress pipeline.

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…