Customer Support Engineer

Outset invented a better way to do research: AI-powered user interviews. Global brands like Hubspot, Microsoft, Uber and Nestle use Outset to achieve deeper, qualitative insights about their users at unprecedented speed and scale. The research industry is massive (>$140B and growing) and ripe for disruption. Incumbents are outdated, slow, and burdened by high-cost services. That's our opportunity. Outset is backed by top Silicon Valley investors and raised a $30M Series B in December 2025—less than six months after our Series A—led by Radical Ventures with participation from M12 (Microsoft’s venture arm), 8VC, Y Combinator, and Adverb Ventures. The raise follows a breakout year, with our business growing 8x as enterprise customers across industries adopt our category, AI‑moderated research, as the new standard for understanding people. We’re a tight-knit team serving some of the world’s largest enterprises. We’re continuing to build our Customer Support team as we scale at Outset! You'll sit between our customers and our product. Day to day, that means owning a live queue of inbound product and account issues, digging into and resolving questions, and collaborating closely with engineering, product, and design. The other half of the job is building: designing the systems, automations, reporting, and training content that will help our team scale our support for customers. You'll partner closely with our NYC-based Product Support Associate, and work alongside Customer Operations, Product, and Engineering. This is a role for someone who is technically capable, AI-native, and excited to dig in with high ownership to define what an AI-native support function actually looks like. Responsibilities - Own the support queue end to end — inbound technical product and account inquiries, resolved with speed, accuracy, and care. - Do advanced troubleshooting: reproduce issues, review logs, and isolate whether something is a product bug, a configuration problem, or a workflow gap. - Write reproducible bug reports Engineering can act on immediately, and follow them through to resolution and customer communication. - Build the deepest product expertise on the CX team, and raise the bar on how well the product is understood internally and externally. - Own and operationalize Pylon, our support platform: ticket routing, automation rules, segmentation, SLAs, macros, and escalation paths. - Design support reporting and dashboards — volume, response and resolution times, deflection, issue categories, per-account health — and turn the data into recommendations leadership can act on. - Build and maintain our knowledge base and internal runbooks. - Prototype and ship AI-assisted support: automated triage and tagging, drafted responses, self-serve deflection, and internal agents that make the team faster. - Turn support signal into product signal — spot trends across tickets and bring evidence-backed insight into product planning. - Partner with Customer Operations on shared workflows, operating model, and documentation. QUALIFICATIONS - 4–8+ years in technical support, support engineering, solutions, or another technical customer-facing role — ideally at a startup with a complex or technical product. - Technical depth: you've reviewed internal logs and used SQL or similar data tooling to debug a customer issue and scope how far it spreads. - Support tooling: hands-on experience configuring a support platform (Pylon, Zendesk, Intercom, Front, or similar) — automations, routing, segmentation — and building reporting on top of it. - Communication: you can explain a technical problem clearly to a non-technical enterprise customer, and go deep on the details with an engineer. - AI curiosity: genuine interest in AI-native tooling, backed by a track record of experimenting with it in your own workflow. - Prioritization and independence: strong prioritization instincts under a heavy queue of inquiries and escalations, steady when things get urgent, and able…