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 100,000 homes and reached over £18m in annual sales.

We are backed by an all-star cast of investors, 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.

The product you see today is just the beginning. We closed our Series A round of funding and are getting ready to build a truly world class and global product.

Now the real work begins - and that is where you come in.


You will be the owner and director of our Operations, Host and Internationalisation team. In particular you will lead the product development in 6 key areas:

  1. Internationalisation: scaling our operations to on-board homes and transact in 20 new cities.

  2. Host experience: concepting and productising the host experience, everything from on-boarding, communications to dashboards and pricing.

  3. Home acquisition: make it easier to find and integrate amazing homes into the collection quickly - by building calendar and price synchronisation solutions that suit both big global partners and individual hosts

  4. Curators’ Community: creating a brand new platform to engage with our team of Home Critics, photographers, and stylists on the ground who find and test our homes

  5. Testing criteria: owning and building on the secret sauce of The Plum Guide - our internal testing algorithm and platform with 250 questions and 350 data points about every single home in our collection. You help decide who’s in or out!

  6. Finance and ops: building intelligence for yield management and working closely with finance to build our global payment systems.

What you’ll get up to

The kinds of things you will be doing include:

  1. Devising the platform’s operational vision and strategy: shaping what features, services and improvements we launch.

  2. Leading your team to concept world class builds including:

    1. Working with hosts and internal teams to really understand pain points and needs.

    2. Converting this understanding into concepts: user stories, visual mock-ups etc.

    3. Running sprints and prioritisation meetings with stakeholders.

    4. Testing and iterating the concept with hosts, staff and experts.

  3. Getting into the nitty gritty details of complex, analytical, and technical projects.

  4. Leading the engineering team to build and ship these products on time, on budget and to an extremely high standard.

  5. Running an always-on program of iteration, testing and improvement.

  6. Coordinating, managing and upskilling a world class squad of engineers.

Who we are looking for

This role does require a very diverse set of skills. As such, we will prioritise hiring people with the right raw talent and attitude, over particular skills. The important thing is that you:

  • Find the idea of building one of the world’s most iconic digital products insanely motivating, and have a super strong vision for what makes a great digital product.

  • Are obsessed with understanding details, and are highly attuned to noticing pain points, needs, niggles and frustrations.  You roll up your sleeves and get into the detail.

  • A “conceptor” at heart: you find it easy to convert your insights into simple, intuitive and emotionally resonant concepts, interfaces and user journeys.

  • Have proven experience in online product management including:

    • Prototyping, spec writing, wireframing and test design.

    • Overseeing and directing UX, analytics, design, research and technical talent.

    • Iterating and improving product development processes.

  • You believe no project is too complex and relish the delivery of them - and have examples of past products and features that you delivered from scratch.

  • You care about being agile and shipping for impact.  

  • You thrive in a fast-paced start-up environment and are comfortable dealing with ambiguity, risk management and changing requirements.

  • Effective written and verbal communication skills, with the ability to present to senior stakeholders.

  • Experience prioritising projects based on impact and business goals and managing stakeholders accordingly.

  • Experience leading technical teams to organise, prioritise and track tasks in a detailed manner. Experience of Scrum is a bonus.

  • Entrepreneurial, self-starter who recognizes where processes can be improved and initiates to improve them.

  • Experience in internationalisation and localisation is a bonus.

  • You are exceptionally organised, and scarily ambitious, with an unreasonably high standard for what is good enough.

  • Able to direct, inspire and drive collaboration between a diverse set of individuals: engineers, designers, researchers and project managers.


  • An opportunity to make a name for yourself as a world-class product visionary - shaping our strategy and directing the global expansion of our host network.

  • Incredible learning opportunities in building and scaling a digital business: Not only will you play a key role in the product development of a VC-backed business, but you will be exposed to all facets of scaling, from fundraising to marketing, engineering to finance.

  • An opportunity to have real impact: shaping our strategy, vision and owning the host and global expansion product direction.

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

  • Competitive salary and generous option scheme (our ambitions are huge and we hope it pays out for all).