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Software Engineer

Portland, OR

Fairly is a fast growing tech-enabled vacation rental management company: we help homeowners earn more from their homes with less hassle, pairing local caretakers with software we build in-house.

We are a small, senior engineering team that works AI-native. We're adding a software engineer to the team, with an emphasis on AI automations: building workflows that use AI to do real work, making them reliable in production, and keeping a person in the loop where judgment matters.

This is a first or early-career role for someone who already builds with AI agents every day and wants to learn how production software gets built and run. You will work alongside senior engineers, in Portland, with real ownership early.

What you'll do

  • Build and ship AI workflows that take a process a person does by hand, do most of it, and route the exceptions to a person.
  • Turn prototypes (Claude skills, n8n flows) into services with proper credentials, logging, monitoring and tests, deployed on AWS.
  • Wear multiple hats across the full software development lifecycle: scope the problem with the people who have it, design, build, test, deploy, monitor and iterate, with support from senior engineers.
  • Design review steps: when the model acts alone, when it drafts for approval, when it escalates.
  • Work with more than one model and compare them on real cases.
  • Sit with the people who own the process, find out what they actually do, and automate that.

What you'll bring

  • A degree in computer science or a related field, or equivalent projects.
  • Daily use of Claude Code or a similar coding agent, and projects you can show, including how you directed the agent.
  • Solid fundamentals in TypeScript or Python, git, SQL and HTTP APIs.
  • Working knowledge of AWS or another cloud, enough to deploy and run what you build (Lambda, containers, queues, or similar), or the drive to learn it fast.
  • Willingness to wear multiple hats: product analyst, developer, tester and operator in the same week.
  • Sound judgment on when to trust model output and when to check it.
  • Clear written and spoken communication. You explain what you built, what it does, and where it can fail.
  • Curiosity about how a business runs.

Nice to have

  • Experience with LLM APIs, tool calling, MCP, or an agent framework.
  • Internship or project experience in React, Node or GraphQL.
  • Familiarity with n8n, Zapier or similar workflow tools.

How we work

  • Small team, high trust, high ownership, with direct access to the CTO.
  • AI-native: we expect you to use coding agents heavily and to improve how we use them.
  • You own your work across the whole lifecycle, from the first conversation with the process owner to monitoring it in production.
  • In person in Portland, with the hybrid arrangement TBD.

How to apply

Skip the resume and cover letter. Email careers@fairly.com with the subject line "Software Engineer: Your Name" and one paragraph answering this:

Tell us about something you built that nobody asked you to build. What did it do, how did you build it (including how you worked with AI tools), and what's one thing it got wrong that you had to fix? Add a link if you can.

We're reading for specifics. If your answer could describe any project, it will not stand out. If it's interesting, we'll ask for a resume and set up a short conversation.

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