Why this role mattersA 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.
This role is located at our Flatiron HQ four days per week.
Annual base salary: 220,000-240,000, plus equity, based on experienceYour ownership and teamReporting 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?
What you will do- 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 monthsThe 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.
Who you areWe 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.
- You have designed transactional systems and APIs or integration platforms that other teams or companies depend on.
- You understand relational modeling, concurrency, consistency, and asynchronous workflows, including what happens when systems fail or disagree.
- You have safely evolved an existing production system and can explain when to extend it, simplify it, or replace part of it.
- You remain a strong hands-on engineer. You make pragmatic tradeoffs and help teammates deliver without becoming the approval point for every decision.
- 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.
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.
How we shipWe move quickly by building quality from the start. A change is done when it is tested, deployed, observable, and safe to roll back. We use AI tools aggressively, but engineers remain accountable for architecture, correctness, and production outcomes.
Explore Engineering at ResortPass, including why we work and what we are building next.
Tech stack- Backend: Ruby on Rails, Node.js
- Data: Postgres, MongoDB
- Search: OpenSearch
- APIs and integrations: REST, OpenAPI, webhooks
- Infrastructure and observability: AWS, Datadog
- Testing: RSpec, Playwright
Benefits- Health, dental, and vision coverage, with ResortPass contributing to monthly premiums
- Stock options
- 401(k) plan
- Unlimited paid time off
- Paid parental leave
- Annual ResortPass credit for pools, beaches, spas, and other experiences
