The Plum Guide
Job title: Technical Product Manager – Operations
The Plum Guide is building a marketplace of the world’s best vacation homes. For real!
We are taking a systematic and obsessive approach to testing every single home on the
planet, accepting only the top 1%. We do so by putting every home through The Plum Test:
an exhaustive hospitality exam, which uses a mix of algorithms and physical visits by
We launched three years ago in London. Since then, we have grown at 15-20% month on
month, expanded to six cities, vetted over 100,000 homes and are tracking over £25M 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. At
the start of 2019, we raised a £14M Series B round from world-class VCs Talis Capital,
Hearst Ventures and Latitude.
We’re trading in 12 cities worldwide and in 6 months’ time we want that number to be 26.
Expanding internationally at this speed requires that our Marketplace (home supply) and
Finance teams are able to operate exceptionally well. Making sure everything we touch when
it comes to money is bulletproof and scalable, and that the logistics of recruiting and
managing hosts across the globe are silky, are both business priorities for the next 12
months. And that’s where you come in.
This is a diverse role, with a wide range of responsibilities — and absolutely crucial for us to
keep growing at hyper speed. You’ll have your own squad of engineers and access to UX and
design resource to make your objectives happen. Day-to-day, you’ll report directly into the
Product Director, with dotted lines into the CFO and Head of Marketplace.
We see this role falling loosely into three buckets:
1. Our financial backend
Understanding and modelling all of our financial requirements, and prioritising the
right projects to make sure our backend systems can deal with them.
Example project: Owning the algorithm for dynamic pricing
Example project: Modelling and vetting new merchant payments providers and
additionally trading in new currencies
Example project: How do we ensure all workflows and booking scenarios are
accounted for in our custom financial ledger system?
2. Our API and supply-side integrations
Our API and integrations with our partners are multipliers on our global expansion
speed, ensuring property managers’ pricing and calendar data is synced
Example project: owning and prioritising the roadmap for the Plum API
Example project: supporting our partners as they onboard with the Plum API
Example project: owning and prioritising third party integrations into the Plum
3. Our internal tools
You’ll need to work closely (alongside our product design team) with our customer
care, finance, supply and demand-side sales teams, to make sure they all have the
tools they need to operate unfairly well.
Example project: Re-imagine our CMS (pretty much our OS) from scratch
Who we are looking for
You don’t need to have prior experience in hospitality or travel. The important thing is that
● A systems-thinker
● Technically comfortable
● Mathematically natural
● Scarily ambitious and with an unreasonably high standard 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.
● Super organised – able to project manage complex processes with multiple
● Target driven and intensely commercial.
● A self-starting learner, confident teaching yourself to do things you have never done
● Someone who’s a team player and a positive, motivating person to be around.
● A role where financially or technically complex projects were the key deliverables,
rather than just a component (required)
● Experience in a global high-growth business (desired)
● A comparable role in fintech, or other heavily compliant industry (desired)
● Salesforce experience would be gold dust (desired)
● An unparalleled opportunity to become an expert in start-up scaling: not only will you
lead the operational expansion in a VC backed business, but will be coached by some
of the best.
● Genuine influence and control: you will work daily with the founders and
management team to shape the company strategy and direction.
● Be an early team member of what we believe will be one of the most famous startups
of the next 10 years.
● Be part of a passionate, friendly and transparent culture: you will be part of
discussions on tech, fundraising, product, brand and global expansion.
● Competitive salary and generous options scheme: our ambitions are huge and we
hope it pays out for all.