Plain is redefining customer support for the next generation of B2B companies. We're building the fastest, most powerful platform to help companies move beyond reactive support and build real customer relationships.
Some of the world's most forward-thinking companies โ including Cursor, Ashby, Vercel, and Granola โ use Plain to unify customer interactions, collaborate faster, and supercharge their workflows with AI.
We're a small, tight-knit team with offices in San Francisco and London, and teammates across Europe. This role is
based in our San Francisco office
, with an expectation of 3+ days a week in person.
The role
As our first Customer Success Engineer, you'll own the technical layer of how customers experience Plain post-sale across the board. That means two things in practice: building the resources that help customers go deep without needing a dedicated CSM, and being the person our CSMs pull in when a customer conversation hits a technical ceiling.
Right now, a lot of what makes customers successful lives in people's heads - in onboarding calls, in Slack threads, and one-off explanations. Your job is to take that knowledge and make it available to every customer, before they have to ask.
You'll be in Plain every single day as you're helping customers, which is a uniquely exciting opportunity to be the end user of the tool. You'll feel every rough edge firsthand, be the first to test new features, and the feedback you generate will immediately feed into the product roadmap.
This role also has real room to grow. Depending on what you're drawn to, it can evolve toward deeper technical ownership (more engineering collaboration and complex implementation work) or towards more account management and customer relationships. We're a small team and we build roles around people who perform.
What You'll Do
- Build the technical foundation customers need to self-serve โ You'll own Plain's documentation, vibe code light PRs, build integration guides, API walkthroughs, and example GitHub repos. When a customer is mid-trial and stuck on their webhook setup at 9pm, your work should be the thing that unblocks them.
- Enable customers to solve problems before they need to ask โ You'll pay close attention to what comes up repeatedly in support and onboarding and be responsible for closing those gaps with whatever works: a doc, a short video walkthrough, a better in-app tooltip, a code example. The medium matters less than the judgment about what's actually causing friction.
This is a great fit if youโฆ
- Have worked in a technical post-sales role at a B2B SaaS company with a developer-facing product.
- Are technical enough to read API docs fluently, write basic TypeScript or GraphQL, maintain a GitHub repo, and ship light PRs. You are comfortable using AI coding tools to move fast and solve problems independently.
- Write clearly and without jargon - you can explain the same concept to a developer and a non-technical buyer and have both land.
- Are a systems thinker - when you see the same problem twice, you fix the underlying cause, not just the instance in front of you.
This won't be the right role if youโฆ
- Are looking for a pure engineering role - you'll be in customer conversations regularly and producing a lot of written content.
- Prefer a clearly defined book of accounts with structured check-ins and renewal targets.
- Need well-defined processes and clear briefs before you can produce work.
- Want a management position right now โ this is an individual contributor role.
- Aren't excited by the idea of working in person โ we work together in our SF office at least 3 days a week.
Compensation Range: $170K - $190K
