Serve as the technical front line for customers by troubleshooting web applications, integrations, APIs, and data issues. Reproduce and diagnose bugs, distinguish configuration problems from product defects, and partner with engineering to resolve issues. Monitor support channels, meet SLAs, maintain documentation, support onboarding, and identify recurring issues and product improvements. Investigate system behavior using logs, dashboards, and SQL while helping build the company’s support function.
About Letter AI
The Role
How We Operate
What's In It For You?
Letter AI is the world’s first revenue enablement platform powered natively by AI. We’re reimagining the end-to-end revenue journey by turning real customer conversations and account data into actionable insights, personalized coaching, meeting prep, and next steps.
Revenue teams aren’t asking for more content or tools. They’re asking for better outcomes. Letter does just that, empowering them to learn faster, sell smarter, and win more.
We recently raised a $40M Series B and are already helping leading companies like Adobe, Lenovo, and Figma transform how their teams work. We 10xed our revenue last year and are looking for the best of the best in Chicago to help us build on that momentum.
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.
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 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
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
- 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 you’ll have meaningful ownership and impact, working closely with top-notch teammates to help build and scale Letter
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