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 do so by putting every home through The Plum Test: a gruelling hospitality exam, which uses a mix of algorithms and physical visits by hospitality experts – our Home Critics.

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. The objectives now are to take Plum global – we launched Paris in March and are ready for more...

The Role

Reporting into the Head of New Markets, you’ll be based in London and lead a team responsible for creating a collection of the best homes & hosts in one of our new launch cities: Rome, Milan, New York & Los Angeles. Your team’s responsibility will be to lead our acquisition journey from testing the home, to the full listing going live on our website.

We only accept the top 1% of homes, and the listings must show this. We’re looking for someone driven, hard working, and motivated by a challenge. If you have insanely good organisational skills, a great eye for visual & written beauty, and are great with people, read on.

What you’ll be up to

It will be fast-paced and change rapidly, but here’s what we expect you’ll spend your time doing.

  • Remotely manage our local city network of photographers & home critics

  • Manage your listing assistant in London

  • Stay one step ahead of the test & photoshoot diary, rescheduling as required

  • Oversee the production of the listings (photos, descriptions, area recommendations) and be the final check for quality control

  • Be the guardian of quality for the new city collection: ultimately deciding what passes and fails the Plum Guide test

  • Obsess over hitting the daily, weekly, and monthly targets for new homes

  • Consistently deliver the acquisition journey on time & budget

  • Communicate our expectations and standards to every host who joins the collection - inspire them to deliver exceptional hospitality and make them proud to join us.

Who we are looking for

This is a long list of the things we’re looking for – you by no means need to check every box. We’re biased towards great attitudes, work ethic, and smarts – everything else can be taught.

  • An incredible people’s person: amazing at persuading and inspiring.  You are super likable, enjoy getting to know people and are great at building relationships.

  • A taste maker: Obsessive about design, style, photography and copy. You have a great eye and a sophisticated taste in design, interiors, food and cultural experiences. 

  • A sharp eye for detail: you notice the small things. A sub-standard photo or badly written copy, would never get past your inspection.

  • Fantastic at giving feedback to get the most out of your creative team in a way they find energising.

  • You are incredibly well organised and love a full diary.

  • You have unreasonably high standards for what is good enough.

  • Super entrepreneurial: You care about getting shit done. And when obstacles inevitably get in the way, you know how to hustle.  

  • A confident self-learner: confident at teaching yourself to do things you have never done before on a daily basis.

  • Excellent spoken & written English for all cities

  • Excellent spoken & written Italian if applying for Rome / Milan role


  • An unparalleled opportunity to become a start-up expert: You will learn how a start-up opens a city, pulls together plans, hires creatives, executes, and builds digital products.

  • Genuine influence to build The Plum Guide collection of homes in the city you work on

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

  • Be part of a passionate, friendly and transparent culture.

  • Work from a buzzing office on Hoxton Square in the heart of London’s start-up world

  • Competitive salary according to experience