CPTO (Chief Product & Technology Officer)

Unit: Digital & Technology City: European Remote, Italy

WeRoad Chief Product & Technology Officer

WeRoad is a fast-growing scale up that is disrupting the travel industry in Italy, Spain, the UK, and now also in Germany and France.


WeRoad is a community of travellers, united by their love for travel, adventure, and discovering faraway lands and cultures. We bring together small groups of like-minded millennials and send them on life-changing experiences to 100+ destinations all over the globe.

Founded in 2017, we're a dynamic, ambitious team of nearly 100 people experiencing exponential growth in Italy and Spain, and expanding in the UK and now also Germany and France. We're on a mission to design and deliver experiences worth living and sharing, rewriting the rules of the travel industry every step of the way.


We are looking for a CPTO to lead WeRoad through its next growth cycle. This newly created position will be part of the Exec team, directly reporting to the CEO. You are required to be highly strategic and influence and shape the strategic direction WeRoad is taking, and ensure that we rewrite the rules of travel industry through taking a technology first approach and thus enabling the scalability of our product and business. As well as setting the future tech strategy, as CPTO you are equally responsible for driving the development of our 5 tech platforms, managing the growth of our tech team from 20 to 70 in the coming years and ensuring strong alignment between technology, product and other business functions. 

You will be expected to show expert knowledge and be well-informed about current technology trends as well as show business acumen and reflect leadership competencies of a corporate rather than a functional leader. 

Responsibilities of the role span digital product vision and strategy, digital product design and development, management of the digital product roadmap, overseeing the development process associated with all our proprietary platforms.

The role report directly to the CEO and be part of Exec team with (currently) three direct reports; 

What you’ll do:

Business Responsibilities  

  • Identify product requirements based both on internal stakeholder and customerì needs (including build, buy and partner decisions) and develop products accordingly; 
  • Align the technology and digital product functions with company strategy, values and business goals and evelop technical aspects of the company’s digital product strategy accordingly; 
  • Set OKRs and technology budgets to assess and measure performance, ensuring profitability of technology;
  • Define, shape and build a long-term, future proof our digital platforms strategy, that builds onto and aligns with the wider corporate goals;
  • Define and oversee the product roadmap, all system design and changes in system architecture;
  • Ensure alignment between business functions through enabling effective communication and transparency across Technology, Tour Operator, Marketing, Finance and other departments;
  • Track, analyse and monitor technology performance metrics;
  • Consolidate technology platforms as needed and create plans for each of them;
  • Drive the evolution of our five core platforms ensuring functionality and efficiency of our systems, while at the same encouraging innovation and the discovery and implementation of new technologies and solutions that will lead to a competitive advantage
  • Website & CMS 
  • Tour Operator management software
  • Travel Coordinators management platforms
  • Booking, Reservation and Payment platform
  • Finance ERP platform
  • Mobile applications
  • Communicate technology and product strategy to the market, customers, partners and investors;
  • Constantly improving end user experience to drive conversions by taking design decision based on data;  
  • Work with Marketing team at strategic level for all the matter about CRO, data marketing automation and martech 

Leadership & Development 

  • Providing strong leadership to a current team of 20, divided into three core areas (1) Engineering , (2) Digital Product and (3) Tech Ops and invest in training and development of skills and capabilities of existing and future team;
  • Shaping and defining the future structure and direction, growing a product and engineering team from 20 to 70 over the next few years;
  • Manage both internal and external communication processes; ensure high levels of influence and collaboration across the organisation, as well as communicating the technology strategy to partners or investors; 

Values & Growth 

  • This role is for the ambitious and entrepreneurial - you are both strategic but equally hands-on and don’t take “no” for an answer;
  • You want to be part of shaping and building a story, and rewrite the rules of travel across Europe and the world;
  • You are passionate about travel and adventure;
  • You can handle high levels of complexity at ease, work under pressure and still provide a clear focus of direction;
  • You are open for feedback, consult, listen and take a continuous improvement approach, making adjustments to your work if necessary to ensure collective success.

Your previous experience/ requirements: 

  • You have worked in an international scale ups
  • You have 10+ years of work experience in the tech field, some of which as a VP, Head of Product, CTO or similar leadership role 
  • You are familiar with our core technology platforms to ensure top-nodge development;
  • You have experience setting and developing strategies;
  • You are a leader, who can bring and develop a team through a period of fast growth and change;
  • You can understand budgets, and business planning;
  • Knowledge of technological trends to build strategy;
  • Ability to conduct customer needs research and technological analyses;
  • You have excellent communication skills;
  • You are Fluent in English;
  • You have a degree in computer science, engineering or other related field; an MBA or other business focused degree is a definite plus

What we can offer:

  • A free WeRoad trip every year to the destination of your choice. You didn't think we'd leave you hanging, did you? Become one of our Travel Coordinators and you could go even more often.
  • A great workspace. WeRoads HQ is based in Milan, where this role is ideally based at, additionally we have 4, soon 6 further hubs all over Europe (Madrid, Barcelona, UK and soon to come Berlin & Paris).
  • Best-in-class benefits. We have a smart working policy, unlimited holiday, and give a bonus to newlyweds and new parents.
  • Fun! We schedule regular team-building events throughout the year and have plenty of opportunities to meet our Travel Coordinators and WeRoaders from all over the world.
  • Stock options & a competitive salary 

Technology we use

These are programming languages we currently have in production:

  • Typescript & Nest.js (new core platform projects)
  • PHP8 & Laravel
  • Node.js (small or legacy projects)
  • Nuxt.js and Vue.js with Server Side Rendering (for all our frontends and back office platforms)
  • React.js
  • Tailwind.css & Buefy
  • Python (for our Business Intelligence pipelines)
  • Elixir & Go (experimental tooling)
  • We use PostgreSQL on all new projects, Redis for caching, and we have other projects running on MySQL and MongoDb
  • We are working on a service oriented architecture where integration & communication between our services is handled with RabbitMQ and our infrastructure runs on Docker containers in Kubernetes on Google Cloud Platform.
  • Everything is configured through Terraform & Helm and automated through Gitlab CI, where we host all our code.
  • We are OpenSource lovers <3

Ready to apply? Here’s what’s next!

  • send us your CV and a short cover letter explaining your fit and motivation to apply for this role
  • introductory call/ culture screen with our Head of People & Culture
  • two technical interviews, one with the CEO of WeRoad and one with the Head of Product
  • final panel interview with the CEO of OneDay and further stakeholders 
  • reference check

Just to let you know, we will try and make as many of these interactions in person!

We can't wait to meet you!

The People & Culture team

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