---
title: 'Support Engineer at Letter AI'
canonical: 'https://feeny.ai/job/support-engineer-letter-ai-chicago-3bqqsd0j103c'
type: 'job'
last_seen: '2026-09-18'
---

# Support Engineer at Letter AI

- **Company:** Letter AI
- **Location:** Chicago, IL
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-09-17
- **Last confirmed live:** 2026-09-18
- **Apply:** https://jobs.gem.com/letter-ai/am9icG9zdDoi3GNxYVgAQE2cAP8KxsSh

## Job description

## About Letter AI

Letter AI (https://www.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.

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

What’s 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 you’ll have meaningful ownership and impact, working closely with top-notch teammates to help build and scale Letter

## About Letter AI

## Company Overview
- **One-liner**: Letter AI provides a generative AI-powered revenue enablement platform that unifies content creation, training, coaching, and buyer engagement to help sales teams execute faster and more effectively.
- **Entity Type**: Private (Series B, $40M raised in February 2026)
- **Headquarters**: Chicago, Illinois, United States (with an office in San Francisco)
- **Founded**: 2023
- **Founders**: Ali Akhtar (CEO) and Armen Forget (Co-Founder & CTO)

## Core Business
- **Primary industries**: Business/Productivity Software, Artificial Intelligence & Machine Learning, Sales Technology
- **Target customers**: B2B – enterprise and high-growth organizations (sales, revenue, and enablement teams)
- **Mission or purpose statement**: Not publicly stated, but the platform’s goal is to “supercharge enablement” by automating the creation of collateral, training, and coaching, allowing reps to spend more time selling.

## Products & Services
- **Letter AI Platform (core)**: A unified, AI-native revenue enablement platform that generates sales content, personalizes it by vertical/customer, provides a real-time AI co-pilot, and scales coaching with AI role-play simulations (including screen sharing for demo practice).
- **Letter Compass (new, August 2026)**: A module that brings conversational intelligence natively into the platform, adding deal intelligence (risk signals), AI-generated documents from calls, structured coaching, and an AI agent that drafts follow-ups and surfaces content automatically.

## Market Standing
- **Valuation/Market Cap**: Not disclosed (private company)
- **Key Metric**: Total funding of **$53.9M** across 4 rounds (Pre-Seed $500K led by Y Combinator, Seed $2.7M led by Formus Capital, Series A $10.6M led by Stage 2 Capital, Series B $40M led by Battery Ventures)
- **Notable Investors/Partners**: Battery Ventures (lead Series B), Y Combinator, Stage 2 Capital, Lightbank, Mangusta Capital, SaaS Ventures
- **Growth Signals**: Headcount grew **278.6% YoY** to 39 employees; rapid product releases (Letter Compass launched August 2026); strong LinkedIn follower growth (+146% yearly); presence across US, UK, India, Brazil; customer logos and case studies indicate production deployments with recognizable brands.

## Competitive Advantages
- **AI-native architecture**: The platform is built from the ground up with generative AI, not bolted on, enabling rapid personalization and automation of content, coaching, and analytics.
- **Unified revenue enablement**: Combines content management, training, coaching, and buyer engagement in one system – reducing the need for multiple disconnected tools.
- **Enterprise security posture**: SOC 2 and GDPR compliant, making it suitable for regulated environments.
- **Speed of innovation**: Frequent product updates (e.g., Letter Compass, AI role-play) demonstrate a fast shipping cadence typical of well-funded startups.

## Strategic Focus
- **Deepening the deal cycle platform**: Integrating conversational intelligence, deal risk signals, and automated follow-ups to cover the entire selling motion.
- **Scaling go-to-market**: Growing the sales and customer success teams (active job postings for Account Executives, CSMs, SDRs) to capture market share in the revenue enablement category.
- **Expanding enterprise adoption**: With Series B funding ($40M) from Battery Ventures, the company is investing in product development and customer acquisition for larger organizations.

## Why Work Here
- **Culture**: High-impact, fast-paced environment typical of an early-stage scaling startup. Employees report high autonomy, close access to leadership, and a “founding” mentality. The trade-off is a demanding pace with evolving processes and potential for change fatigue.
- **Work policy**: Hybrid – Chicago office requires three in-office days per week; San Francisco office also available. Remote options exist for some roles.
- **Notable perks**: Not explicitly listed, but the combination of strong funding ($53.9M), rapid growth, and “founding” roles suggests significant ownership and career acceleration opportunities. The company emphasizes individual autonomy and direct impact on product and revenue.
- **Engineering culture**: Small technical team (10 people, 19% of workforce) with high ownership; likely strong focus on AI/ML and full-stack development. Recent job postings include Full Stack Engineer.

## Sources
1. [LinkedIn](https://linkedin.com/company/letter-ai)
2. [PitchBook](https://pitchbook.com/profiles/company/528122-17)
3. [Built In – Company Profile](https://builtin.com/company/letter-ai)
4. [Built In – Workplace Perception](https://builtin.com/company/letter-ai/faq/workplace-perception)
5. [Gem Careers](https://jobs.gem.com/letter-ai)

## Other roles at Letter AI

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- [Marketing Coordinator](https://feeny.ai/job/marketing-coordinator-letter-ai-chicago-jkk82t3grjzn) — Chicago, IL
- [Sales Engineer](https://feeny.ai/job/sales-engineer-letter-ai-chicago-7w8hkw3z1rp1) — Chicago, IL
- [Sales Development Representative](https://feeny.ai/job/sales-development-representative-letter-ai-chicago-as0tgn9pzrag) — Chicago, IL
- [Enterprise Account Executive](https://feeny.ai/job/enterprise-account-executive-letter-ai-chicago-rpmeqj8feyfm) — Chicago, IL
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