Support Engineer (SF) at Plain

WHO ARE PLAIN? 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 — including Cursor, Ashby, Vercel, and Granola — 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. We tend to start our work days earlier to overlap with our EU colleagues (7:30-8am), but we promise to provide the coffee/tea ☕ and morning tunes 🎵. THE ROLE This is not a "ticket taker" role. As one of our Support Engineers, you'll be a clear owner of support during SF hours and a key member of a growing support function. You'll combine technical depth, strong judgment, and proactive communication to ensure customers, and the rest of the company, always feel support is under control. You'll be joining a small, lean, and mighty CX team distributed across SF and the EU. You'll work directly with Product and Engineering, act as "customer zero" for the product we're building, and help shape how support operates at Plain as we scale. Many of our customers are technical, so you'll regularly move between APIs, webhooks, SDKs, logs, and architecture discussions and then translate that complexity into clear, confident guidance for customers. You'll have real ownership and immediate influence in how support and the product itself evolves. If you've ever wanted to build the support experience you wish you'd had at previous companies, this is that opportunity. WHAT YOU'LL DO - Be the primary owner of the support queue during SF hours, ensuring customers get timely, thoughtful responses, even when the answer isn't immediately clear. - Be "customer zero" for the product: Represent the voice of real support teams. What works, what doesn't, and what's missing? - Drive issues end-to-end: investigate, debug, coordinate with engineering, and follow through until resolution. - Own clean, visible handover between EU and US timezones so nothing drops on the floor. - Proactively flag risk early (backlogs building, customer frustration, L2 pressure, product bugs). - Help define and evolve how we do support: ownership models, handover norms, escalation standards, documentation, and tooling. - Improve our Help Center and self-serve experience to reduce repeat questions and scale quality. - Partner closely with Product, Customer Success, and Engineering as a sounding board when scoping and designing features. THIS IS A GREAT FIT IF YOU… - Have experience as a Support Engineer in an early-stage or scaling B2B SaaS company. - Are technically strong: you can read logs, write SQL, understand APIs, webhooks, and how systems work under the hood. - Take initiative by default — you don't wait to be told what to own. You ask questions, you're curious, and you're constantly looking for opportunities to optimize your own work. - Communicate clearly and proactively, especially when things are messy or high-pressure. - Have strong opinions about support products and practices, and enjoy improving them. - Are commercially minded and understand customer context (Tier, lifecycle stage, sentiment, impact). - Thrive in ambiguity and love to solve problems - the power of Plain is the ability to extend it. You think creatively and love finding different ways to solve a customer's use case. THIS WON'T BE THE RIGHT ROLE IF YOU… - Prefer to spend most of your day coding rather than working directly with customers. - Need well-defined processes before you can operate confidently. - Are uncomfortable making judgment calls and owning outcomes. - Are looking for a people-management role right now. - Expect the pace, perks, or structure of a large, established company. - Aren’t interested in working in person or up for early mornings - this role is based in SF, and we work together in the office at least 3 days a week. We tend to start earlier in the day (7:30/8am or so).