Support Engineer

Letter AIChicago, IL
$80,000 - $110,000

About The Position

Letter AI is seeking a Support Engineer to join their team. This role will serve as the technical front line for customers, owning customer-reported issues from diagnosis to resolution. The Support Engineer will work closely with the engineering team and have a significant impact on shaping the product and the support function itself. This is a hands-on, high-impact role at an early-stage company.

Requirements

  • 2-4 years of experience in a technical support, support engineering, or software engineering role, ideally at a B2B SaaS company
  • Strong troubleshooting and debugging skills, with comfort reading code (Python, JavaScript/TypeScript) even if you're not writing production features day to day
  • Familiarity with APIs, web applications, and basic database/SQL concepts
  • Excellent written and verbal communication skills, with the ability to explain technical concepts clearly to both customers and engineers
  • Highly organized, with strong ownership of customer issues from first report through resolution
  • Past experience or strong interest in generative AI
  • Highly collaborative mindset with strong problem-solving skills

Responsibilities

  • Serve as the primary technical point of contact for customer-reported issues, troubleshooting problems across our web app, integrations, and APIs
  • Reproduce, diagnose, and triage bugs, distinguishing between user error, configuration issues, and genuine product defects
  • Partner closely with engineering to escalate, track, and resolve technical issues, providing clear reproduction steps and context
  • Monitor support channels and ensure timely, high-quality responses that meet our SLAs
  • Build and maintain internal documentation, FAQs, and troubleshooting guides to reduce repeat issues
  • Identify patterns across customer issues and proactively flag product improvements to engineering and product teams
  • Support customer onboarding and technical enablement as needed
  • Use logs, dashboards, and SQL to investigate the data and system behavior behind reported issues

Benefits

  • $80k–$110k base salary, depending on experience, plus variable compensation
  • Letter stock options
  • Comprehensive medical, dental, and vision coverage
  • 401(k) with company match
  • Company-supported commuter, connectivity, and wellness benefits
  • Daily lunch in our Chicago and San Francisco offices
  • Happy hours, dinners, events, and offsites
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