Would You Rather Be

Head of Sales

Award-winning careers education app for schools seeking superstar salesperson to launch our sales team!

About Would You Rather Be

Would You Rather Be is an award-winning career discovery app for schools. We’ve spent the past two years building a game-changing AI-powered career assessment that is fun and accurate.  

We match people to careers based on their interests and then tell them exactly what they need to do to get into each career, along with the time and cost for them personally. We even show them their transferable skills for each career based on their work history.

We won an award through the CareerTech prize run by Nesta and the Department for Education. We’ve had 80,000 users and over 80% rate us 4 or 5 out of 5 stars.

Our mission is to help everyone find career happiness. It’s a social mission, and we want to start by helping all school pupils in the UK work out what career to pursue that would make them happy. We want to democratise access, so that every pupil in every school has equal access. We’ve recently signed up our first few schools and now we want to accelerate our efforts here…

About the Role

We’re building our sales team from scratch. And we’re looking for the best sales people to join us on our journey.

We’re open to all levels of seniority - whether you’ve got 2 years or 20 years sales experience. What matters is that you care about our mission. You’ll be instrumental in giving all school pupils from all backgrounds equal access to the best career guidance software available.

It’s a greenfield opportunity. As we’re just starting out, you’ll have all 4,000 UK schools to target. You can apply your own strategy as to how you go about this challenge. And you’ll be selling a product that is new, innovative and exciting. Plus there’ll be tremendous learning and growth opportunities for you as we scale into schools around the UK. And we’ll pay generous commissions if you’re successful!


  • Experience in B2B tech sales, managing the full funnel from lead generation to closing the sale and ad-hoc customer management - essential
  • Enjoy working independently - essential
  • Able to learn quickly and hit the ground running - essential
  • Personable, confident and driven to meet sales targets - essential
  • Experience selling into UK schools or colleges - strongly desirable
  • Experience selling EdTech - desirable


  • £40,000 - £50,000 salary depending on experience, plus up to 50% commission
  • Remote role - work anywhere in the UK, with ability to have occasional meetings/catch-ups in London
  • Co-working space allowance of £300 p/month if you don’t want to work from home
  • Want the latest mac? We’ll give you any tech you need to do your job well
  • Sales software systems of your choice - you get to choose the processes you think work best
  • Pension contribution of 5%