Staff Software Engineer (Backend Booking Platform & APIs)

• A day pass is sold by capacity. A cabana is reserved as a unit. A massage needs a time slot and available resources. Each has different rules for inventory, pricing, and cancellation. Those rules must remain correct wherever a booking begins
• We are hiring a Staff Engineer to lead the evolution of our booking platform and external API. You will help distribution partners and authorized AI agents book the same inventory as ResortPass guests
• You will build on a production Rails OpenSearch and Postgres system while shaping important decisions about its future. What you build will determine how quickly we can launch hotel and spa partners and new experiences. You will see your architectural choices through to real bookings and help other engineers build on them
• Reporting to the Head of Engineering, you will lead architecture and the technical roadmap for the booking domain and external API. This is a hands-on individual contributor role: you will write core production code and guide implementation with other backend engineers
• Our Distinguished Engineer will be your partner on architectural decisions that affect the wider platform. You will work directly with the Head of Engineering and engineering leads on priorities, sequencing, and capacity
• With Product, Partnerships, and hotel operations, you will assess partner requirements and plan launches. Your judgment will help determine what belongs in the shared platform, where a simpler integration is sufficient, and what to defer
• Problems you will help solve
• A partner times out after requesting the last available cabana. How can it determine whether the booking succeeded, retry safely, and give the guest a clear answer?
• A massage needs a time slot, provider, or room, while a day pass uses capacity. Which concepts should they share, and where should their booking rules differ?
• Evolve clear models and boundaries for products, pricing, availability, holds, and reservations. Represent category differences explicitly and use real requirements to guide what becomes shared
• Build and launch a versioned external API for pricing, availability, holds, booking, changes, and cancellations. Establish access controls, documentation, and a practical path from partner testing to production
• Make booking operations reliable through retries, timeouts, and partial failures. Design idempotency, concurrency controls, webhooks, and reconciliation to prevent duplicate bookings and inventory errors
• Establish reusable patterns for supply, property management, and point-of-sale integrations. Make data ownership and failure handling clear so engineers can add connectors and diagnose problems consistently
• Lead incremental migrations in our existing system. Set reliability and latency targets, test important failure scenarios, and ensure the team can observe, operate, and safely roll back changes
• Help engineers take ownership of larger problems through focused design reviews, pairing, and mentoring. Explain tradeoffs, resolve decisions across team boundaries, and follow the work through production
• What success looks like in 6–12 months
• The first priority is to prove a dependable production booking path. We will then use what we learn to add partners and categories, with Product and Partnerships sharing responsibility for commercial launches
• An initial distribution partner can use the API for the booking lifecycle, from pricing and availability through confirmation, changes, and cancellation
• Additional partners reuse those contracts and integration patterns, reducing the bespoke engineering needed for each launch
• Booking correctness, reliability, latency, and recovery meet agreed targets under real usage, with automated coverage of important failure scenarios
• At least one new experience category uses the shared booking capabilities, and other backend engineers can independently extend the platform and launch connectors

Benefits

• ResortPass Credit: We practice what we preach – employees get annual ResortPass credits to enjoy daycations!
• Company Equity: We believe in the work we do and take pride in having a real stake in our shared success.
• Unlimited PTO: We offer a flexible PTO policy, so that you can take time off when you need it and come back rested and recharged.
• Holistic Benefits: We offer benefits to support your whole self—including health insurance, commuter perks, paid parental leave, and more.- You understand relational modeling, concurrency, consistency, and asynchronous workflows, including what happens when systems fail or disagree
• You have designed transactional systems and APIs or integration platforms that other teams or companies depend on
• You remain a strong hands-on engineer. You make pragmatic tradeoffs and help teammates deliver without becoming the approval point for every decision
• Ruby on Rails experience is useful, but not required. Experience with marketplaces, reservations, inventory, payments, or public APIs will help. We encourage you to apply even if you do not match every line
• You communicate clearly, listen carefully, and build trust with engineers and business partners. You can challenge an assumption and change your mind when the evidence changes
• You have safely evolved an existing production system and can explain when to extend it, simplify it, or replace part of it
• We care more about demonstrated impact than a previous Staff title. You may have 9+ years of experience or a track record of equivalent depth and scope
• You have led substantial technical work across multiple engineers or teams, from an ambiguous business problem through launch and operation