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.
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.
- 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.
- 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.
Seniority level
- Mid‑Senior level
Employment type
- Full‑time
Job function
- Sales and Business Development
Industries
- Health and Human Services
#J-18808-Ljbffr…