The Plum Guide is building a marketplace of the world’s best holiday homes. For real!

We are taking a systematic and obsessive approach to testing every single home on the planet, and accepting only the top 1%.

We launched 18 months ago in London. Since, we have vetted over 80,000 homes and on track to reach over £10m in annualised sales. We are backed by an all-star cast investor group including Local Globe (TransferWise, OneFineStay, Citymapper), Alex Chesterman (Founder of Zoopla), William Reeve (Founder of Love Film), Alex Saint and Troy Collins (Founders of Secret Escapes), Errol Damlin (Founder of Wonga) Jason Goodman (Founder of Albion) and many more.

We recently closed our Series A round of funding and are now taking Plum global. We launched Paris in March and now have Rome, Milan, New York & Los Angeles in our sights...

The Role

To launch a new city we need a collection of amazing homes and this role is part of a London based team hunting down the best hosts with the most beautiful homes in Rome, Milan, New York & LA. Once found, your job is to make these hosts insanely excited by the opportunity to join Plum.

There’s a light & a dark side to this role.

On one hand, it’s an unparalleled opportunity to become a start-up expert. You will learn how a start-up plans to open a city, executes, and builds digital products. You will strengthen your sales skills in ways that will serve you for life and learn how marketing is done properly. You will also be managing a team of 2 Italian Business Development Associates.

On the other hand, we have ridiculously high standards and we’ve not launched 4 cities simultaneously before - things will get intense, your team is inexperienced and not everything will go to plan. You’ll need to be driven, motivated by a challenge and possess an infectious positivity to enjoy this ride.

What you’ll be up to

This is our wish-list. If you were everything on it, we’d worry that you weren’t real!

  • You’re a great people person and engage in conversation easily
  • You’re good at reading people and flexing your style to suit
  • You love goals, numbers, and get a thrill from beating targets
  • You know how to inspire a team & help them hit their targets
  • You’re ridiculously well organised
  • You’re hugely determined and willing to stick at a task until you succeed
  • You’re not scared of speaking your mind, taking and giving feedback
  • You’re super action-oriented and entrepreneurial
  • You believe that the ability to sell is a core life skill whoever you are
  • You have 1-3 years email & telephone sales experience
  • You have excellent spoken & written English & Italian


  • Become a start-up expert

  • Make your mark by building something tangible in a matter of months

  • Learn & strengthen skills that will serve you for life

  • Be a member of what we believe will be one of the most famous start-ups of the next 10 years

  • Work from a buzzing office on Hoxton Square