Mid-Market Account Executive
3 days ago
Otford
Job Title: Mid-Market Account Executive 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 “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 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.