At a Glance
- Tasks: Drive sales in the dental tech space, owning the entire sales cycle from start to finish.
- Company: Toothfairy is revolutionising dental care for modern workplaces with a digital clinic approach.
- Benefits: Uncapped commission, equity options, and a remote-first work environment.
- Other info: Join a high-trust team where your ideas shape the future of dental care.
- Why this job: Make a real impact by solving dental access issues for employees across the UK.
- Qualifications: 5+ years in B2B SaaS sales, ideally in HR tech or benefits.
The predicted salary is between 42000 - 84000 € per year.
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. You will use AI and data as a competitive advantage throughout the sales cycle, not to replace human selling, but to sharpen insight, prioritisation, and decision-making in complex deals.
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. Use AI-assisted analysis to identify deal risk, stakeholder gaps, next-best actions, and prospect engagement across your pipeline.
- 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. Use AI to tailor commercial narratives to different stakeholder concerns within the same account.
- 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. Contribute insight on how AI can be applied across the sales motion to improve win rates, not just volume.
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. Hands-on experience using AI tools to enhance deal strategy, account insight, forecasting, or stakeholder management in complex sales cycles.
- 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. AI-native but sceptical: you use AI where it creates leverage, not because it's fashionable.
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.
- A Sales Role Built for the AI Era: You'll be expected to use modern AI tools to sell better, not harder, as we scale a category-defining GTM motion.
Mid-Market Account Executive in London employer: Toothfairy TM
At Toothfairy, we pride ourselves on being an exceptional employer that champions innovation and employee autonomy in a remote-first environment. Our culture fosters high trust and collaboration, allowing you to take ownership of your role while contributing to a meaningful mission that transforms dental care for the modern workforce. With uncapped commission potential and opportunities for professional growth, joining our team means being part of a dynamic company that values your contributions and empowers you to make a real impact.
StudySmarter Expert Advice🤫
We think this is how you could land Mid-Market Account Executive in London
✨Tip Number 1
Network like a pro! Get out there and connect with people in the industry. Attend events, join online forums, and don’t be shy about reaching out on LinkedIn. The more connections you make, the better your chances of landing that Mid-Market Account Executive role.
✨Tip Number 2
Prepare for those interviews! Research Toothfairy inside out—know their mission, values, and how they’re shaking up dental care. Be ready to discuss how your experience aligns with their goals and how you can contribute to their success.
✨Tip Number 3
Showcase your sales skills! During interviews, share specific examples of how you've closed complex deals or navigated multi-stakeholder environments. Use the SPICED framework to demonstrate your consultative selling approach and how you tackle challenges.
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets noticed. Plus, it shows you’re genuinely interested in being part of the Toothfairy team. Let’s get you that dream job!
We think you need these skills to ace Mid-Market Account Executive in London
Some tips for your application 🫡
Be Authentic:When you're writing your application, let your personality shine through! We want to see the real you, so don’t be afraid to show your passion for the role and what makes you tick.
Tailor Your Application:Make sure to customise your CV and cover letter for the Mid-Market Account Executive position. Highlight your relevant experience in B2B sales and how it aligns with our mission at Toothfairy. We love seeing how you can contribute!
Showcase Your Achievements:Don’t just list your responsibilities; share your successes! Use numbers and specific examples to demonstrate how you've closed deals or built relationships in previous roles. We’re all about results here!
Apply Through Our Website:We encourage you to apply directly through our website. It’s the best way for us to receive your application and ensures you’re considered for the role. Plus, it shows you’re keen on joining our team!
How to prepare for a job interview at Toothfairy TM
✨Know Your Stuff
Before the interview, dive deep into Toothfairy’s mission and services. Understand how they’re revolutionising dental care and be ready to discuss how your experience aligns with their goals. This shows genuine interest and helps you connect your skills to their needs.
✨Master the SPICED Framework
Since the role involves complex sales cycles, brush up on the SPICED framework. Be prepared to explain how you’ve used it in past roles to manage deal complexity and forecast accuracy. This will demonstrate your consultative selling skills and strategic thinking.
✨Showcase Your AI Savvy
Toothfairy values the use of AI in sales, so come armed with examples of how you've leveraged AI tools in your previous roles. Discuss specific instances where AI helped you enhance deal strategy or stakeholder management, showing that you can adapt to modern sales techniques.
✨Build Relationships on the Spot
During the interview, think about how you can build rapport with the interviewers. Ask insightful questions about their experiences and challenges in the industry. This not only showcases your relationship-building skills but also positions you as someone who values collaboration and communication.
