Hi! 👋 I'm Josh, Chief Product Officer at WeTravel 🇳🇱

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.

To increase the value we generate for these travel businesses and how we monetize it, I’m hiring an operational leader in Amsterdam to incubate and scale new initiatives around “instantly bookable" Supplier Booking Marketplaces and Demand-as-a-Service.

About this role & structure

Tech scaleups exist to create value for their users and increase the enterprise value of itself. New initiatives are important in that process, but come with chicken-and-egg challenges. You don’t know whether it will work or how it should work until you’ve tried it. Until those are known, it’s difficult to dedicate product & engineering efforts.

That’s where this hands-on operational leadership role comes in.

• For the first ~2 quarters, you will report to me (CPO) to rapidly iterate on the market understanding and Ops-led MVPs with minimal engineering support, while ensuring the MVPs we test reveal the path to scalable productization. This phase will be a combination of scrappy, seed-stage startup Ops work combined with long-term strategic thinking.

• Once 1-2 initiatives have a clear path to scalability as well as dedicated product management and engineering staffing, you will have an opportunity to lead the commercial outcomes of those initiatives at scale.

• At that point, we will examine the ideal long-term reporting structure for you, including options to report to our VP of CX Davis. We will collaboratively design the long-term structure rather than prescribing it to you.

• For example, Custom Website is a new initiative at a more advanced stage—and the commercial and operational leader reports directly to Davis. But for this early stage, we’ve seen benefits of being closer to the Product and Engineering organizations.

Responsibilities in your first ~2 quarters

You will incubate both Supplier Marketplace Bookings and Demand-as-a-Service over the next ~2 quarters.

At this 0-to-1 stage, having two new initiative areas to own will allow you to maximize the business upside from your weekly time. The upside and likely velocity are unknown. One pre-scale project is unlikely to consume a senior operator’s full-time capacity. There are external factors like how one project can be blocked by a vendor for a few days at a time.

Supplier Marketplace Bookings

Success in 1-2 quarters:

• Launch marketplaces for top 4-5 categories (probably hotels, activities, transfers, cruises, and flights) with reliable and profitable vendor relationships.

• Scaled monthly WeTravel gross profit across all marketplaces to $20,000/month with minimal engineering support. The exact target should be proposed by you and aligned on together.

• Drove alignment on how WeTravel should prioritize this initiative long-term, what revenue to expect at scale, and how to get there across Product and Ops investments in 2027.

• Created a momentum and systematic way to understand/track progress.

How you might get started in your first 2-3 weeks:

• Take over and expand/deepen vendor research and negotiations from our Head of Business Operations. Must check the supply breadth and depth, whitelabel flexibility, booking experience, reporting functionality, SSO feasibility, general API quality, and vendor stability.

• Partner with our Product Marketing Manager to increase traffic to the marketplace vendors gradually—and eventually take over this responsibility. The gradual approach is due to the unknowns about the quality of experience the vendor will provide our clients and their travelers.

• Deepen our understanding of how WeTravel clients discover and transact with suppliers to help us hone in on what marketplaces to offer to whom. This can include interviews, surveys, pilots, competitive benchmarking, and more.

• [Stretch goal] Use AI tools to prototype booking marketplace vendor integrations to prove out feasibility, run user research, and drive various decisions.

Demand-as-a-Service

Success in 1-2 quarters:

• Ran pilots for two or all of the below for multiple months to have sufficient insights to drive investment decisions going into 2027:

  • Paid ads

  • Social contents (likely AI assisted)

  • Blogs (likely AI assisted)

• Scaled monthly WeTravel gross profit across Demand-as-a-Service to $50,000/month with minimal engineering support. The exact target is TBD but the bar is higher because Demand is expected to be more “servicey”, leading to a higher OpEx burden than Supplier Marketplace.

• Helped land at least 30 new clients due to their interest in Demand-as-a-Service. These clients would have to have at least $300,000/year GTV potential. This metric may end up being more important than gross profit at the early stage. Also, our 2026 north star remains GTV while revenue (or gross profit) will become increasingly important in 2027 onwards.

• Drove alignment on how WeTravel should prioritize this initiative long-term, what revenue to expect at scale, and how to get there across Product and Ops investments in 2027.

• Created a momentum and systematic way to understand/track progress.

How you might get started in your first 2-3 weeks:

• Take over the AI blog writer prototype from our AI Acceleration PM. Get it to the point of being pitch-able to clients, without $ fee commitments. Launch a (probably unpaid) pilot to get feedback and start to examine willingness to pay. It could also be more efficient to run usability test motion rather than a pilot. We may also have achieved this by your start date.

• Scope out paid ads pilot including target organizer profile (and list), written pitch, and how exactly the service would work behind the scenes during the pilot phase. Start socializing internally for feedback.

• Benchmark competitors and industry examples for all three Demand-as-a-Service offerings, identify vendors and start taking demos (e.g. social content likely requires a specialized AI tooling vendor), and start strategic yet action-oriented discussion groups.

What we are looking for

• Passion to start and scale new B2B customer value propositions and revenue from it. Disciplined enough to kill a program or a particular approach to a program that doesn’t work, even if it’s become a baby. Optimizes for the enterprise value, not their own OKR. Thrives in ambiguity and can build something out of nothing.

• 7+ years experience in operations and product incubation roles in tech companies. Ideally in scaleups and ideally in B2B domains (even if the company is B2C).

• Founder-like balance of strategic instincts combined with “get it done” hands-on mindset. Lack of patience for bureaucracy and slowness, while respecting org-wide consistency, are pluses.

• Battle-tested commercial experience including vendor evaluation and negotiations, upsell motions, and proving out the commercial viability of new initiatives.

• Comfort with analytics across product, operational, and financial domains. Knowing what questions to investigate and how to communicate the “so what” is mandatory.

• Unafraid to fill in where engineering resources are not yet available, such as AI-driven prototyping and API evaluations.

• A background in demand generation, tech-enabled as-a-service businesses, travel supply, and marketplaces is a strong plus.

• Travel industry experience is a plus but not required.

Interview process

All of WeTravel interview processes aim to be high-signal and respectful of your time. For the Product Org, at least two interviews will be realistic working sessions. We do not include a take-home assignment. Every interview will include time for your questions.

First round

• Recruiter screen (30 minutes): Introduction, background, and motivation.

Second round

• Manager interview (45 minutes): Behavioral discussion and a live jam on one of the two initiatives.

• Head of CX interview (45 minutes): Behavioral discussion and a live jam on one the other initiative.

Final round

• Product Org calibration with a Lead Product Manager (45 minutes): Assessment on (i) how the candidate would fit into the Product Org and (ii) types of projects and support that would set the candidate up for success.

• CEO conversation (30 minutes): A two-way discussion about mission, ambition, and culture.

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!