Hi! 👋 I'm Josh, Chief Product Officer at WeTravel 🇳🇱
I’m hiring my design partner to take the WeTravel product into its next stage of rapid growth. I want to give you the full context of the opportunity.
Multi-day travel businesses (think of a 7-day safari in the Serengeti or a 5-day scuba diving trip in the Galapagos) use WeTravel as their end-to-end operating system to manage sales processes, collect payments, and run their back offices. Our powerful payment stack and AI-enabled solutions help them grow sales, save money, and save time. As a result, travel businesses can focus on delivering incredible bucket-list experiences.
Our Situation
WeTravel 1.0
WeTravel started in 2015 and focused on solving the reservation and payment needs of multi-day travel businesses, an industry that collectively sells over $250B of travel annually. This included enabling a travel company to book more than 400 students on a graduation trip, each with personalized packages. It also included dramatically reducing friction and costs in international payment collection. This initial product-market fit powered nearly eight years of strong growth, a successful Series B raise, and resilience through COVID.
WeTravel 2.0
After solving reservations and payments, we learned that our clients still struggled with inefficient sales processes and back-office operations. Much of their work involved moving data across multiple systems and relying on spreadsheets that did not scale with their businesses.
Over the last two years, we expanded WeTravel beyond transactions into the workflows that surround them. We built an AI-assisted itinerary creator and a travel-specific CRM to improve sales processes. We added an automated liability waiver tool and passport information collection to simplify back-office operations.
Today, tens of thousands of travel businesses are beginning to use WeTravel as an end-to-end operating system, as depicted below.
WeTravel 3.0
Building on our successful 2.0 and our recent Series C funding, we are working towards the next stage of WeTravel with three major investments:
Continuing to build the end-to-end operating system for multi-day travel businesses so they can do most of their work in one system.
Adding AI features to assist travel businesses and increasingly do the work for them.
Becoming an industry network, not just a software system. Multi-day travel businesses work with many partners to curate, sell, and operate trips. We are now helping them find those partners, coordinate with them, and pay them within WeTravel.
These investments represent a shift in both scope and ambition. WeTravel is now rapidly evolving into a true operating system with multi-player workflows, AI assistance, and network effects. To make sure we achieve this product ambition, we want to elevate our product design practice. For example:
Our design team is already strong at creating features to solve individual pain points. Now we want to raise the bar on quality, velocity, and cohesiveness across the entire product so that WeTravel operates as a unified system.
Our UX is a mix of modern surfaces and 2015-era surfaces. This is a natural outcome of years of fast growth. We now need to evolve toward a cohesive, modern look and feel. That evolution needs to be thoughtful and efficient, rather than disruptive.
We taught ourselves how to design AI features. Now, we are ready to deepen our expertise in using AI to create user value across key workflows, while avoiding the common trap of treating AI as a solution in search of a problem.
Product Design Team
Many vertical SaaS and FinTech companies focus on feature coverage over usability. We have prioritized usability, especially simplicity, from the beginning and have invested steadily in our design function. Our design team is amazing, tight-knit, and hungry to learn and grow, particularly in building AI features and delivering business impact through design.
Our Lead Designer has served as a player-coach for years and now wants to focus fully on being a senior IC. This creates the right moment to bring in a dedicated leader and coach for the team. I want to build one of the best design studios in Amsterdam, a studio that others look up to and learn from.
Company Overall
WeTravel is a 300+ person company representing more than 50 countries. We combine global diversity with the agility and closeness of a much smaller team. More than 70 colleagues are based in our Amsterdam office in Rokin, including the entire Product Org and more than 60% of Engineering.
You will have fun innovating fast with brilliant, low-ego colleagues. Everyone is accessible. For example, both the CEO’s and my calendars are completely public. Our clients are also easy to reach, which helps us stay close to their needs and build with them.
Financially, WeTravel is highly secure and growing fast, with 50 to 100 percent year-over-year growth depending on the metric. This gives us a strong foundation to build from.
About The Role
The Head of Product Design is the chief designer and a strong design team manager. They are a builder and a teacher, not an OKR bureaucrat. We plan OKRs and roadmaps only as tools to sharpen our focus.
Below are the high-level responsibilities in prioritized order. I consider every interview a learning process for myself as well, and I welcome feedback on this list if we get to meet.
Build
Design the whole product experience as the design partner to the CPO. With your design leadership, the WeTravel product should clearly improve in functionality, cohesiveness, and adoption at least every 6 months.
Guide designers to craft features that feel simple, obvious, and cohesive across the product. The Head of Product Design is accountable for raising the bar on design details, down to the microcopy, through the team’s work.
Strengthen our design system and our processes, within the design team and with stakeholders, so we continuously improve both quality and velocity.
Manage
Coach every designer to improve their craft and other aspects of being a great WeTravel designer, including business understanding. Each designer should feel proud of how they have grown in at least one dimension every 6 months.
Maintain and add to our vibrant, tight-knit design studio culture. Champion that ambitious craftsmanship culture across the Product & Engineering Org and across the Amsterdam office. This includes being present in the Amsterdam office 3 to 4 days a week as one of the cultural leaders.
Hire the best design talent in Amsterdam at an appropriate pace while maintaining a consistent and disciplined level-band approach.
Keep Things Connected to Customers and the Business
Deepen our understanding of our customers and their customers. Guide designers and others to blend the voice of customers, data, and first-principles thinking to drive clear decisions.
Contribute to defining the multi-quarter roadmap by working backward from the customer value we want to deliver and the stories we want Sales and Marketing to tell.
Keep every effort tied to business outcomes. These outcomes do not have to be quantitative.
An Ideal Candidate
Is an exceptional product designer and design leader with a strong track record of driving business outcomes through both craft and leadership.
Has led a significant, product-wide UX evolution to accelerate growth.
Has built several business AI features, from leading the design hands-on to guiding adoption and iteration based on real feedback.
Has built relevant B2B SaaS and FinTech products such as CRM systems, task management tools, Canva-like creator tools, business wallets, or traveler checkout flows.
Has enough years of experience to credibly lead this scope with earned wisdom. This is difficult with fewer than 12 years in design or fewer than 4 years as a manager. Management experience does not need to be contiguous. If you have been a multi-layer manager for many years, this role may not be the right fit.
Would strengthen our global, collaborative, low-ego and ambitious culture.
Interview Process
Our process aims to be high-signal and respectful of your time. Two of the interviews will be realistic working sessions. We do not include a take-home assignment. Every interview will include time for your questions.
First round
Second round
Manager interview (45 minutes): Behavioral discussion to deepen our understanding of your design and management approaches.
Team interview with Lead Designer and Lead PM (45 minutes): Two working sessions. First, you will walk us through a live demo of a product where you owned the end-to-end design, helping us understand your choices and your guidance to others. Second, our team will share a draft Figma design for you to review and give feedback.
Final round
Product vision jam with Lead Designer and CPO (90 minutes): A collaborative working session using real research and a storyboard to explore product vision and key UX elements together.
CEO and/or founder conversation (30 minutes): A two-way discussion about mission, business ambition, design leadership, and culture.
Benefits
Competitive salary.
Generous "Time to Recharge" policy - enjoy unlimited paid time off to rest, recharge, and show up as your best self.
Work remotely for a maximum of 4 weeks per calendar year.
2-week cross-functional onboarding program.
Annual team off-site (often somewhere sunny 🌊).
Cycle-to-work scheme (Swapfiets subscription) or commuting reimbursement.
Tuesday team lunches and after-work social events.
Beautiful office in central Amsterdam - rooftop garden and right by Rokin metro.
Extensive paid family leave.
Three paid volunteer days per year - take time to give back to causes you care about, on us.
Cutting-edge equipment and tools to set you up for success.
Join an international, travel-loving team with a passion for adventure and innovation.
A Final Note
Thank you for taking the time to digest this full context. Our clients are entrepreneurs and artisans who pour their passion into creating bucket-list experiences, including some who have honed their craft over multiple generations. Their passion motivates us to build the best possible tools for them and to scale an ambitious business of our own. If you want to share this obsession with our design team and with me, we would be excited to get to know you.
Equal Opportunities
WeTravel is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome applicants from all backgrounds, experiences, and perspectives. If you're excited about this opportunity and believe you're a good fit, we encourage you to apply and join us in transforming the travel industry!
