Please note we are working remotely until July. Details to follow on flexible working for the foreseeable.

The Company

Plum Guide is on a mission to build the definitive collection of the world’s best holiday homes. We are taking a systematic approach to vetting every single home on the planet and accepting only the top 3%. Like a Michelin Guide, but for homes. We do it by putting every home in a destination through a systematic vetting process, which includes identifying candidate homes through proprietary AI, interviewing hosts and sending our Home Critics to visit and test nominated homes in person.

We launched 5 years ago. Since then we have grown incredibly quickly; expanded to 254 locations in 15 countries; tested over 150,000 homes; and developed a customer experience that’s returning the highest NPS scores in the industry.

We are backed by some of the world’s top entrepreneurs and VCs. These include the founders and backers of TransferWise, Citymapper, Zoopla, Secret Escapes, BuzzFeed, Appear Here, Graze, LoveFilm, and many more. Our focus for the next 12 months is on hyperscale and hypergrowth: taking Plum truly global. This is where you come in.

The Role

Our portfolio of homes comprises individual homeowners, small and medium local businesses, and large property management companies with hundreds, sometimes thousands, of Plum homes. The Head of Enterprise Sales will be responsible for the commercial success of those large property management companies on Plum. They will build our sales, business development, and account management functions tailored for larger organisations. 

A member of our leadership team, they’ll work cross functionally with marketing, guest sales, customer service, finance, and legal. They will also work closely with the product, tech, and integrations teams to develop the digital experience for large partners.

We’re looking for a proven leader in the space to build one of the most important functions at Plum and have a direct impact on our growth. 


  • Pitch to and sign new deals with large partners - at least two a quarter
  • Codify the sales process for large accounts - including lead generation and qualification, pitching and negotiating, and successful onboarding
  • Build the sales CRM and systems required to increase the output of the sales team quarter over quarter 
  • Account manage existing large partners 
  • Develop and implement a scalable account management / business development framework to:
    • Drive quarter over quarter growth in sales for our large accounts
    • Improve partner satisfaction working with Plum
  • Hire, train, and grow a team as Plum and the number of strategic partnerships grows
  • Evolve our commercial model and offering to drive commercial success for both Plum and partners
  • Improve the conversion of large partners on Plum 
  • Improve the NPS of large partners 
  • Refine the process to curate, filter, and upgrade homes from large partners to grow their supply pool that qualifies for Plum
  • Develop new revenue streams with large partners


  • Fluent in English, other European languages a bonus 
  • 5+ years of experience in key account management, sales, and business development 
  • Experience building sales and account management processes from scratch 
  • An exceptional salesperson, able to demonstrate consistent achievement of targets, and revenue impact on previous organisations 
  • Highly commercial, relentlessly focused on driving growth for the business with a good understanding of the levers to do so 
  • A good decision-maker with strong judgement - uses analytical skills (quantitative and qualitative) to inform commercial and operational decisions 
  • High emotional intelligence and a positive attitude, and a great listener
  • An excellent communicator and leader, with experience building and motivating teams and working cross functionally 
  • Independent self starter who takes initiative and thrives in a fast-faced, dynamic environment
  • Experience using Salesforce is a plus but not essential


  • Join what we hope will be one of the most famous travel brands in the next 5 years - at the ground level
  • Work with the co-founders and senior team on a regular basis
  • Build your own function from scratch with autonomy 
  • See the direct impact of your work on the business
  • Competitive salary, benefits, and stock options

Plum Guide is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status’.

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