Support Engineer

Letter AI•Chicago, IL

5d•Hybrid

About The Position

Letter AI is the world's first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Adobe, Lenovo, and Figma to ramp up faster with AI-powered training and coaching, instantly find and personalize collateral for customers, and engage their buyers with the industry's first AI Sales Room. We recently raised a $40M Series B led by Battery Ventures, with participation from existing investors including Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and Formus. The round comes just four months after announcing our Series A, indicating a shift we're seeing in real time: revenue teams aren't asking for more content or tools. They're asking for better outcomes, and Letter AI is bringing those outcomes to life! We 10Xed our revenue last year and are looking for the best of the best to join us on the adventure 📈. The Role We are looking for a Support Engineer to join our team and be the technical front line for our customers. You will own customer-reported issues end to end — diagnosing problems, working directly with our engineering team to resolve them, and helping shape a product that gets better with every ticket. This is a hands-on, high-impact role at an early-stage company, where the support function itself is still being built and you'll have real influence over how it works.

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