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Founding Backend Engineer

About this role

Outbound's backend is the source of truth for generated trips, readiness, eligibility, persistence, subscriptions, recovery, and the product state the mobile app has to trust. This role owns the systems that make flexible planning feel reliable.

The hard part is not just calling models or tools. It is turning reasoning, retrieval, state, and side effects into durable contracts so travelers see a clear product instead of a pile of fragile generated text.

Key deliverables & responsibilities

1. Trip generation and state architecture

  • Build and harden APIs and services for chat, trip generation, itinerary persistence, trip status, retries, and recovery.
  • Preserve canonical planning state, generated fields, partial states, degraded signals, and user-visible readiness across the full backend path.
  • Design typed contracts so model output becomes usable product state rather than loose text passed downstream.

2. Infrastructure and reliability

  • Own production backend reliability, logging, alerting, error handling, and cost-aware model/tool usage.
  • Improve auth, session, entitlement, async job, notification, and storage boundaries where the product needs them.
  • Build supportable observability that helps the team debug real issues without exposing planner machinery to travelers.

3. Product engineering partnership

  • Work closely with mobile to trace backend truth through API models, domain entities, state, and UI projection.
  • Write contract tests, smoke tests, and focused regression checks around generation, refresh, retry, and payment/subscription-sensitive paths.
  • Make pragmatic founding-engineer tradeoffs: small enough to ship, strong enough that the product promise survives real use.

What success looks like

  • Trip generation, retry, refresh, and recovery flows are observable, reliable, and honest when data is partial.
  • The mobile app receives stable contracts and no longer loses important generated fields or invents local truth.
  • The backend can support early real users without requiring constant manual inspection to understand what happened.

What we are looking for

  • 5+ years building production backend or product infrastructure, ideally in a small team where ownership is broad.
  • Strong API design, data modeling, async workflow, persistence, reliability, and observability judgment.
  • Comfort with TypeScript/Node, serverless or cloud infrastructure, and the tradeoffs of shipping production systems early.
  • You can reason about AI product systems as stateful software, not just prompts and responses.
  • You are careful about source-of-truth boundaries and know how subtle contract drift becomes user-facing product damage.
  • You communicate clearly with product and mobile collaborators and can separate evidence from inference when debugging.

Bonus if you

  • Experience with AWS Lambda, API Gateway, DynamoDB, S3, CDK, queues, or event-driven architectures.
  • Experience with OpenAI or LLM-backed product systems, structured outputs, retrieval, tool use, or evaluation.
  • Experience with travel, maps, recommendations, subscriptions, payments, or consumer mobile products.

Apply for this role

Send a short note and include work that shows how you think: a portfolio, shipped product, teardown, writing sample, GitHub, resume, or anything concrete.