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

Based in London you’ll lead a two-continent team responsible for curating & maintaining the collection of homes & hosts that launch Plum in Rome & Milan. It’s fast paced, and requires a rare mix of creative, commercial & people skills...

  • Be the guardian of quality for our Rome & Milan collections: ultimately deciding what passes and fails the Plum Guide test.

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

  • Be comfortable balancing the speed of a start-up, with the quality of the Plum proposition

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

  • Obsess over hitting the monthly booking & guest happiness targets that prove the success of your collection.

  • Recruit & train the Community of Home Critics & Photographers in each city to deliver world class work.

  • Deliver feedback to hosts after guest stays to help improve their service & deliver the Plum promise. Also decide which homes to re-test or remove from the collection.

  • Be the main point of contact for our management companies and serviced apartment companies (who have many homes in their portfolio). Ensure our relationships with those accounts are strong commercially and that they maintain high quality standards.

  • Cultivate your community of hosts, making Plum their favourite platform. Do so through creative communication, connecting hosts & benefits programmes.

  • Continuously innovate our process: use guest and host feedback to generate new and better ways of doing things. Implement these new ways and roll them out globally.

Relevant qualities

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

  • 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.

  • World-class at giving feedback to get the most out of your creative team & hosts in a way they find energising.

  • You are incredibly well organised to stay on top of the action across 3 time zones

  • 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.  

  • For a creative, people’s person you are weirdly obsessed about the business numbers

  • Excellent written & spoken English & Italian

  • 3+ years of experience is beneficial but not a must-have.


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

  • If you make your objectives happen, you will inevitably be one of the most sought out talents in the start-up, creative and hospitality industry.

  • Genuine influence to perfect The Plum Guide in Italy

  • Be one of the earliest team members of what we believe will become a very famous brand

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

  • Competitive salary and options scheme: our ambitions are huge and we hope it pays out for all.