Customer Support Engineer

Outset.ai

$100K — $120K *
Technical Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 4-8+ years in technical support or a technical customer-facing role, preferably at a startup with complex products.
  • Experience in reviewing internal logs and utilizing SQL or similar tools for debugging.
  • Hands-on experience with support platforms (Pylon, Zendesk, etc.) including automation and reporting.
  • Ability to communicate technical issues clearly to non-technical customers and discuss details with engineers.
  • Genuine interest in AI tools, with a history of integrating them into workflows.
  • Strong prioritization skills and independent work ethic in high-pressure situations.
  • Proactive ownership attitude, willing to take initiative beyond defined responsibilities.

Responsibilities

  • Own and manage the support queue for technical product and account inquiries with speed and accuracy.
  • Conduct advanced troubleshooting to identify product bugs, configuration issues, or workflow gaps.
  • Draft clear and actionable bug reports for engineering and track their resolution and customer communication.
  • Build in-depth knowledge of the product to enhance internal and external understanding.
  • Manage Pylon’s support platform, including ticket routing and automation rules.
  • Design support performance dashboards and reports to inform leadership decision-making.
  • Create and maintain a comprehensive knowledge base and internal runbooks for team use.
  • Develop and implement AI-assisted support features to enhance efficiency and customer engagement.

Benefits

  • Opportunity to build and define an AI-native support function from the ground up.
  • Collaborative work environment partnering with product and engineering teams.
  • Role in a fast-paced startup setting, with potential for significant impact.
  • Professional development opportunities through involvement in shaping the support process.
  • Ability to work from a central location with a dynamic team, fostering easier collaboration.
Full Job Description
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 to find structure in ambiguity without waiting for a defined process.
  • Ownership: you take responsibility beyond your lane and want the range that comes with a small, fast-moving team.
  • Based in the San Francisco Bay Area, able to work onsite from our SF office, with hours that overlap meaningfully with East Coast colleagues.

Nice to have
  • Experience being an early or founding support hire and developing process at scale.
  • Experience supporting enterprise customers.
  • Familiarity with user research, research ops, or participant recruitment workflows.
  • Interest in testing and tinkering with newly-launched and in-development features.

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