Mid-Market Account Executive in Otford

Location: Remote (UK)

Type: Full-Time

Salary: Up to £140k OTE Uncapped (£70k 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 a Mid-Market Account Executive, reporting directly to the Chief Revenue Officer, you’ll own the Mid-Market pipeline 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 Sales Cycle: Own deals from first conversation through to close, with full accountability for pipeline quality, velocity, and conversion. Run complex, multi-threaded sales cycles, typically £75k–£150k+ ARR. Deliver predictable revenue against a £800k+ 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 Insurance / 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.
• 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.

What You’ll Bring

• Experience: 5+ years in Mid-Market 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 £75k+ ARR deals and carrying £800k+ 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.
• Sales Craft: Fluent in SPICED for complex 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.

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.