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.
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