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.

We launched 2 years ago in London. Since then, we have grown 20% month on month, vetted over 80,000 homes and reached over £11m in annualised sales! We are backed by an all-star cast investor group including Local Globe (TransferWise, OneFineStay, Citymapper), Octopus Ventures (Secret Escapes, Eve, Tails), BGF Ventures (Trouva, Roli, Gousto), 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 have just closed our Series A round of funding and are going on a fast-paced expansion drive.

The Role

At Plum, we aim to be famous for two things:

  • Our “science behind the perfect stay”: our rigorous methodology for testing and vetting the top 1% of homes in every city.   
  • Our Match Making Service: our team of travel consultants (a.k.a Match Makers) who, powered by data, help match guests with their dream home and neighbourhood.

Designing, building and leading this Match Making team will be your role.

To date, our Match Making team consists of 6 people. They spend their day on the phone, email, LiveChat and WhatsApp, working with guests to find them their dream home.

While our Match Making offer is already loved  by our customers, we are at the foothills of developing it. We haven’t yet properly defined the proposition, or put in place a proper CRM system, processes, training, KPIs and hiring principles. 

This will be your role. Specifically, you will have hit the ball out of the park in your first 12 months, if:

  1. As a team, you hit your revenue target (you will own the business revenue number).
  2. You increase our sales per Match Maker threefold.
  3. Create such a wonderful Match Making experience that guests:
    1. Give us an 80+ NPS score, after booking (i.e. they enjoy the interaction with us).
    2. Give us an 80+ NPS Score after their stay (i.e. the matchmaking really works).
  4. You have turned our match making service into a scalable, repeatable engine.

What you’ll be up to

This is a highly entrepreneurial role that will quickly evolve and morph. However, to bring it to life, here is what you can expect to be doing:

  • Designing and innovating the Match Making proposition: defining what it is exactly, how we package it, how we communicate it, the processes and systems for delivering it and the kinds of people we hire.
  • Leading and managing the Match Making team daily, ensuring they hit their sales and customer satisfaction targets (NPS).  
  • Implementing a CRM system and processes to turn our Match Makers into an effective, scalable and as far as possible, automated, sales machine.
  • Continuously optimising our process to:
    • Improve our conversion from enquiries to profitable sales.
    • Improve our match making abilities (i.e. The NPS score guests give us)
  • Hiring and managing the team: from the 6 members today, to about 16 with-in 12 months.
  • Upskilling your team in everything from sales techniques to management practices.
  • Devising our customer service processes, systems and policies: occasionally problems arise meaning our Match Makers have to step in and resolve any customer issues and concerns.
  • Turning our current 12 hours/7 days a week operation, into a 24/7 operation.
  • Being part of the leadership team and inputting into the overall direction of the company.

Who we are looking for

This role really does require a very diverse set of skills. The important thing is that you:

  • Find the idea of designing one of the world’s most famous sales and customer service teams insanely motivating.   
  • Are an amazing sales person: truly target driven, highly persuasive and well trained in sales techniques.
  • Have a proven track record implementing a (scalable) sales process, CRM systems and KPIs, resulting in exponential revenue growth. 
  • Proven experience hiring and managing successful sales teams.
  • A clear communicator and experienced manager; able to set expectations quickly and deal with underperformance promptly.
  • Scarily ambitious and with an unreasonably high standard for what is good enough.
  • Highly analytical: able to deconstruct problems logically & solve them using data, insight & gut. 
  • A motivating, inspiring and energetic individual: able to attract talent and inspire them to deliver the best work of their lives.
  • Passionate about city travel with plenty of first-hand experience staying in luxury accommodation.
  • Experience in the following areas a big plus:
    • Working with our target market: 40-60-year-old affluent urban creatives.
    • Dealing with customer complaints and conflict resolution.
    • Travel sector experience.


  • An unparalleled opportunity to make a name for yourself as a world class sales leader and customer experience designer.  
  • If you make your objectives happen, you will inevitably be one of the most sought out talents in the global start-up, hospitality and technology scene.
  • Genuine influence and control: you will join the leadership team and work as an equal with the founding team in setting the strategy and vision for Plum. 
  • Incredible learning opportunities in building and scaling a consumer brand: Not only will you lead the Sales function of a VC backed business, but will be exposed to all facets of scaling a digital business: fund raising, marketing, engineering, finance and ops.
  • Be the 20th team member, of what we aim to be, one of Europe’s most famous start-ups.
  • Competitive salary, bonus and generous options scheme: our ambitions are huge and we hope it pays out for all.