Hi! 👋 I’m Ismayil, Engineering Manager for Team Payments at WeTravel.
We are the merchant of record for payment acceptance on our platform. When a trip does not happen, the chargeback lands on us, not the trip organizer. A trip can be booked today and depart 18 months from now, so our exposure on it stays open that entire time. That is a different shape of risk from most payments work, and I am hiring an engineer to own it. You would join a team of 10+ engineers and work every day with our Product, Payment Operations, and KYC/Verification team.
About WeTravel:Think of the most incredible adventures imaginable: trekking to Machu Picchu, cycling through Tuscany, or going on a safari in Kenya. For years, the small businesses and local experts who run these trips have been stuck using messy spreadsheets, countless emails, and complicated payment methods.
WeTravel is changing that. We build the tools that empower any entrepreneur to launch and grow their own travel business. Our platform makes it simple for organizers to create beautiful trip proposals, securely process payments, and manage their customers, so they can focus on what they do best: creating amazing experiences.
This is one of the last great frontiers of travel to come online, and as the category leader, we are at the forefront of this change. Last year alone, our platform was trusted by 8,000 organizers to lead over a million travelers on adventures in 150+ countries. Now, we’re on an exciting journey to grow from powering $2B to $10B in travel experiences per year.
We believe that every trip, when done right, can be a force for good - and we’re building the engine to make more of that possible.
What's the role:Every organizer collecting payments on WeTravel passes through a series of decisions: whether they can sell their trips and products here, how much of their payout we hold back and how quickly we release it, and what happens when a good account starts going bad. Today these decisions are still largely manual and they will not scale to $10B. Your job is to make them sharper and faster, and to take the manual work out of them. You will own the systems behind them.
Some major problems worth solving:
Assessing an organizer at signup and then through the life of the account, so how much we hold payout and how quickly we release it reflects how strong the business actually is.
Reserves that track what an organizer actually owes their suppliers on a given trip, so a hold reflects real forward obligations rather than a flat percentage.
Exposure, disputes, balances, payout history, and verification state in one place, so a decision takes minutes rather than hours.
What you’ll do day-to-day:
Lead projects end-to-end: discovery with Product, Payment Operations and our KYC/Verification team, solution design, build, rollout, and the monitoring that proves it works.
Shape how we decide, not only how it gets built. What we assess, what we measure, and which manual steps automation should take over are all yours to influence.
Weigh protection against user experience. Anything you build has a cost to a legitimate organizer, and finding that balance is part of the work.
Own the reliability of what you ship, and help raise the engineering bar across the team.
We’re focused on the impact. We don’t subscribe to any one framework or execution ideology, and we adapt based on what’s impactful.
We’re using the latest hardware and constantly on the look out for better tools & ways to work.
We have AI-first development experience and work with the latest models and agentic dev tools.
Stack: We’re developing React/TypeScript, Ruby on Rails and Kotlin Microservices. Our services run on Kubernetes. We also use and love MongoDB, MySQL, Postgres, Cockroach DB, Snowflake and we’re working with the major LLM providers.
Basic qualifications:
7+ years of product engineering expertise, with 4+ years dedicated to risk, fraud, or underwriting systems that move real money.
Deep expertise in the systems that decide about money, such as exposure and credit models, decision and rules engines, holds, reserves and payout limits, transaction monitoring, and the ledger those balances sit on.
Strong backend mastery in Ruby on Rails, Kotlin, Python, Go, Java, or Node.js with the agility to ramp up on Ruby quickly.
Direct production on-call experience, including authoring post-mortems and leading incident response.
Excellent written and verbal communication skills, including cross-functional collaboration experience, and the ability to thrive in a distributed, multicultural environment.
Pragmatic adoption of AI tools to optimize your engineering workflow, including the ability to mentor and train others on AI concepts.
Preferred qualifications:
Experience at a merchant of record, payment facilitator, marketplace, or lender, where the platform carried the loss rather than passing it on.
Experience automating an underwriting or periodic review program that previously ran on manual review.
Your risk expertise is limited to tuning rules in a vendor dashboard like Stripe Radar or Persona. We need someone who builds the engine underneath and owns what it does to real balances.
You are hesitant to take full ownership of mission-critical money movement or participate in the on-call rotation when systems fail.
You need complete data and settled requirements before you will commit to a decision. Risk work means making the call on partial information and sharpening it as more arrives.
You are looking for a siloed IC position without the need for cross-functional collaboration or product-level discovery.
You require a rigid, pre-defined roadmap; we prefer to sharpen our strategy and direction as we scale the team.
On most risk teams you move a rate by a fraction of a percent. Here a single decision you design is worth six figures.
Make a real impact: you’ll help build the operating system for the multi-day group travel industry, empowering thousands of organizers and millions of travelers worldwide.
Solve meaningful technical challenges at scale, from designing robust systems to improving real-time user experiences in a complex domain.
Be part of building the best engineering team: you’ll help shape culture, mentor others, and contribute to high standards of excellence and collaboration.
Enjoy flexibility and balance, with competitive compensation, generous PTO, and remote-friendly work culture.
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.
Monday/Thursday team lunches and after-work social events.
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.
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!
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory



