Opportunities from Plain (ashby)

Plain is redefining customer support and customer success for the next generation of B2B companies. We’re building the fastest, most powerful platform to help companies move beyond reactive support and build meaningful customer relationships. Some of the world’s most forward-thinking companies - like Cursor, Vercel, and Granola - trust Plain to unify all customer interactions, enable faster team collaboration, and supercharge their workflows with AI. We have offices in SF and London. This role is hybrid with 3 days a week in our SF office. Because we work closely with our teammates in Europe, we start early, but you’ll find quiet afternoons for heads-down work. WHY THIS ROLE IS SPECIAL Our most strategic customers do not arrive through self-serve. They arrive with an existing support setup, a lot of context to migrate, and workflows that do not exist in Plain yet. Getting them live is genuine engineering work, and today that work lands on the core engineering team. It gets done, and it gets done well, but it moves the roadmap around more than we want it to. That is the gap this role closes. You own that work end to end, which means customers get an engineer whose entire job is their problem, and the core team gets a clearer run at the product. The other half of the job is deciding which of that work should stop being bespoke and become product, so the same thing never gets built twice. WHAT YOU'LL DO

• Work directly with customers to diagnose the problem, scope the fix, and ship it end to end.
• Own the system design for customer deployments, trading off correctness, scale, and speed as the situation demands.
• Explain the plan and the tradeoffs to whoever is in the room, engineer or not.
• Work with Sales, CX, Product, and core Engineering to get what you learn into the roadmap.
• Help define how the Forward Deployed function runs as it grows. THIS IS A GREAT FIT IF YOU…
• Have built and shipped full-stack products end to end. You are at home in modern frontend (React and TypeScript) and you write backend that holds up in production.
• Prototype quickly and learn from real usage. You would rather put something in front of a customer and change it than get the design right on paper first.
• Communicate exceptionally well. You can run a customer call, turn a vague ask into concrete scope, and write it up so nobody has to ask what was agreed.
• Have strong product sense. You can separate what a customer asked for from what they actually need, you know which one-off work should turn into product and which should stay one-off, and you have the taste to decide whether it is worth building at all.
• Own the outcome without much scaffolding. This is an IC role in an early-stage, ambiguous environment, and you do not wait for clean requirements before unblocking someone.
• Stay calm when things get tense. Delays, bugs, and de-scoping conversations come with the job, and you can say yes to the reasonable asks while pushing back on the rest. OUR TECH STACK We choose tools that empower both humans and AI:
• Frontend: React and TypeScript
• Backend: TypeScript and GraphQL
• Cloud: AWS, Cloudflare, and multiple LLM providers
• Tooling: GitHub Actions, Datadog, Terraform, and more The stack keeps evolving with whatever works best. THIS WON'T BE THE RIGHT ROLE IF YOU…
• Want a heads-down role with no customer contact.
• Have little patience for customer messiness.
• Over-engineer, and chase perfection at the cost of speed.
• Struggle to say no, or take every request at face value.
• Only thrive with detailed specs and stable requirements.