---
title: 'Customer Success Manager at Letter AI'
canonical: 'https://feeny.ai/job/customer-success-manager-letter-ai-chicago-vs1s7ym0a1fm'
type: 'job'
last_seen: '2026-09-11'
---

# Customer Success Manager at Letter AI

- **Company:** Letter AI
- **Location:** Chicago, IL
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2024-07-04
- **Last confirmed live:** 2026-09-11
- **Apply:** https://jobs.gem.com/letter-ai/am9icG9zdDp3J1ybNGA-bPOHzF7vQyEF

## 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 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 in Chicago to join us on the adventure 📈.

## The Role

We are looking for an early Customer Success Manager to join our expanding Customer Success team. You will play a meaningful role in helping define how we support and engage our customers as we scale. In this role, you will own key aspects of the customer success journey and ensure both existing and new customers derive maximum value from our platform.

- Own day-to-day customer relationships, serving as the primary point of contact and trusted partner for our clients
- Deliver a high-touch, highly responsive customer experience, with frequent touchpoints and fast turnaround on customer needs
- Onboard new customers and guide pilot customers through successful conversion and long-term adoption
- Proactively monitor customer health and engagement, quickly identifying risks and taking action to ensure retention and success
- Actively gather customer feedback and partner with the product team to continuously improve the customer experience
- Build deep relationships with customers by understanding their goals, challenges, and definition of success
- Collaborate closely with Sales and Marketing to support renewals, expansions, and upsell opportunities

Qualifications for the role include:

- 3+ years of experience in customer success, account management, or a related field
- Proven track record of managing customer relationships and driving customer success
- Strong problem-solving skills and ability to think strategically about customer needs
- Excellent communication and interpersonal skills
- Ability to work in a fast-paced startup environment and manage multiple priorities
- Experience with customer success tools and platforms is a plus

As a part of the team at this early stage, you will not only receive a competitive salary and benefits, but also a meaningful equity stake in the company.

## 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

Join us on this exciting journey to build the world's next generational sales tech company. We look forward to hearing from you!

## 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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