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About 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.
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
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
Skills
- Python
- JavaScript/TypeScript
- APIs
- Web applications
- SQL
- Generative AI
Location
- Chicago
- San Francisco
Work Type
- Full-time
- Onsite
Experience Level
- 2-4 years
Salary/Compensations
- $80k–$110k base salary, depending on experience, plus variable compensation
Benefits
- Letter stock options
- Comprehensive medical, dental, and vision coverage
- 401(k) with company match
- Company-supported commuter benefits
- Company-supported connectivity benefits
- Company-supported wellness benefits
- Daily lunch in our Chicago and San Francisco offices
- Happy hours, dinners, events, and offsites
About the Company
- Letter AI is the world's first unified revenue acceleration platform powered natively by generative AI.
- Our platform empowers sales teams at customers like Lenovo and Redpanda 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.