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.

The product you see today is but a mere prototype. We have just closed our Series A round of funding and are getting ready to build a truly world class (global) product. Now the real work begins.

That is where you come in.

The Role

You will be the owner and producer of our digital product (a kind of chief product officer). In particular you will lead the product development in 3 key areas:

  1. The Customer Experience: developing new features and services to improve the customer experience (NPS).
  2. Site conversion: aiming to double our site conversion in the next 12 months.
  3. The Science Behind The Perfect Stay: This is the formula and tools we use to test homes and select the top 1%.

To give you a sense of what success looks like, you will have hit the ball out of the work after 12 months if:

  1. Our NPS score has risen to the top 0.1%ile of the travel sector.
  2. Our conversion has doubled.
  3. Our product feels highly differentiated (we’ll share more when we meet!)

What you’ll get up to

The kinds of things you will be doing include:

  1. Devising the product vision and strategy: shaping what features, services and improvements we launch.
  2. Leading your Product Squad to concept world class builds including:
    1. Working with customers to really understand pain points and needs.
    2. Converting this understanding into concepts: user stories, visual mock-ups etc.
    3. Testing and iterating the concept with customers, staff and experts.
    4. Converting the concepts into technical specs and user journeys.
    5. Working with your designer to convert the concept into wonderfully simple and beautifully attractive user interfaces.
  3. Leading the engineering team to build and ship these products on time, on budget and to an extremely high standard.
  4. Running an always on program of iteration, testing and improvement.
  5. Building, managing and upskilling a world class Product Squad consisting of a researcher, UX designer, visual designer, back end engineers and front-end developers.

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 succeeding in building one of the world’s most iconic digital products, insanely motivating.
  • Have a super strong vision for what makes a great digital product.
  • Are obsessed with understanding the customer and highly attuned to noticing pain points, needs, niggles and frustrations.
  • A “conceptor” at heart: you find it easy to convert your insights into simple, intuitive and emotionally resonant concepts, interfaces and user journey.
  • Have proven experience in online product management including:
  1. Prototyping, spec writing, wireframing and test design.
  2. Overseeing and directing UX, design, research and technical talent. 
  3. Running sophisticated A/B testing.
  4. Designing product development processes
  5. Launching multiple successful products, ideally across multiple platforms (iOS, Android, and Web)Have a beautiful eye: an impeccable taste in design, aesthetics and usability.
  • You believe in brand and design being critical to building a world class product.
  • Have an intense (almost) maniacal attention to detail.  
  • Commercial, with good business sensibility.
  • Scarily ambitious and with an unreasonably high standard for what is good enough.
  • Super action oriented: you care about getting shit done and shipping amazing products.
  • Able to direct, inspire and drive collaboration between a diverse set of individuals: engineers, designers, researchers and project managers.


  • An unparalleled opportunity to make a name for yourself as a world class product visionary.
  • Incredible learning opportunities in building and scaling a digital business: Not only will you lead the product development of a VC backed business, but will be exposed to all facets of scaling: fund raising, marketing, engineering, finance and ops.
  • If you make your objectives happen, you will inevitably be one of the most sought out talents in the London start-up, hospitality and technology scene.
  • Genuine influence and control: shaping our strategy, vision and owning the customer 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).