2-4 years of experience in technical support, support engineering, or software engineering, ideally in B2B SaaS
Strong troubleshooting and debugging skills, comfortable reading code (Python, JavaScript/TypeScript)
Familiarity with APIs, web applications, and basic database/SQL concepts
Excellent communication skills, able to explain technical concepts to diverse audiences
Highly organized approach to owning customer issues from report to resolution
Interest or experience in generative AI
Collaborative mindset with strong problem-solving skills
Responsibilities
Serve as the primary technical contact for customer-reported issues
Reproduce, diagnose, and triage bugs, identifying user error versus product defects
Work closely with engineering to escalate and resolve technical issues
Monitor support channels for timely, high-quality responses
Create and maintain internal documentation and troubleshooting guides
Identify patterns in customer issues to suggest product improvements
Support customer onboarding and technical enablement when needed
Utilize logs, dashboards, and SQL for issue investigation
Benefits
Comprehensive medical, dental, and vision coverage
401(k) with company match
Company-supported commuter, connectivity, and wellness benefits
Daily lunch provided in offices
Team events such as happy hours and dinners
Ownership through stock options
Opportunity for meaningful impact in a fast-growing startup
Full Job Description
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 you9ll have real influence over how it works.
Your key responsibilities will include:
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
Qualifications for the role include:
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 you9re 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
How We Operate
At Letter AI, we want you to be unapologetically you while operating with our core principles in mind:
Customer-obsessed: Make your customers unreasonably happy and everything else will fall into place
Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization
Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues
Driven yet humble: Push for excellence and deliver fast, but keep your humility
What9s in it for you?
Compensation: $80k-$110k base salary, depending on experience, expertise, and expected impact, plus variable compensation
Ownership: Every full-time teammate receives Letter stock options, so you can share in the value you help create
Benefits that have you covered: Comprehensive medical, dental, and vision coverage, plus a 401(k) with company match
Benefits for the everyday: Company-supported commuter, connectivity, and wellness benefits, plus daily lunch in our Chicago and San Francisco offices
Team events: Happy hours, dinners, events, and offsites with a team that genuinely enjoys spending time together
Build with us: Join a fast-growing startup where you9ll have meaningful ownership and impact, working closely with top-notch teammates to help build and scale Letter
