Mid-Market Account Executive
3 days ago
Sevenoaks
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. 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. • 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., • 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., • 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., • 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., • 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., • 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., • 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., • Fluent in SPICED for complex deals., • Strong consultative seller with Challenger instincts., • Comfortable running senior, commercial conversations without hiding behind slides., • 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., • 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., • 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., • Mid‑Senior level, • Full‑time, • Sales and Business Development, • Health and Human Services #J-18808-Ljbffr
Chef & Cook
Waiters
Bar Staff
Retail
Kitchen Porter
Barista
Quick Service
Accounting & Finance
Art, Media, Design
Child Care
Cleaning
Construction & Trades
Customer Service
Driver & Delivery
Education
Engineering
Entertainment
Events & Promotion
Health & Social Care
Host & Hostess
Information Technology
Legal
Management
Manufacturing
Office & Admin
Sales & Marketing
Security
Sports & Wellness
Other