---
title: 'Account Executive at Letter AI'
canonical: 'https://feeny.ai/job/account-executive-letter-ai-chicago-4cca0a4cs12p'
type: 'job'
last_seen: '2026-09-11'
---

# Account Executive at Letter AI

- **Company:** Letter AI
- **Location:** Chicago, IL
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2024-10-18
- **Last confirmed live:** 2026-09-11
- **Apply:** https://jobs.gem.com/letter-ai/am9icG9zdDpXB0xdOjIi6X5yhY_IsQDY

## 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

As an Account Executive at Letter AI, you will play a key role in driving our revenue growth. This is an opportunity to take full ownership of the sales cycle—from identifying leads to closing deals. You’ll be working with complete autonomy in a rapidly growing market, significantly impacting the company's growth and your own career development. The freedom to build, experiment, and create your own sales strategies will be unparalleled, as you help shape the go-to-market (GTM) function in a dynamic AI-driven startup.

Why Join?

- Exponential Growth Potential: Be part of an early-stage startup in a transformational space, where there’s massive opportunity for expansion and your contributions can significantly influence the company's trajectory.
- Autonomy & Impact: You’ll have the freedom to make key decisions, experiment with new approaches, and truly own your role.
- AI-Powered Platform: Work at the forefront of AI technology, helping sales teams deliver real impact with AI (see our work with [Lenovo](https://www.letter.ai/case-study-lenovo) and [Redpanda](https://www.letter.ai/case-study-redpanda)).
- Build from the Ground Up: This is a rare opportunity to be part of something bigger, crafting and shaping the GTM function for a fast-growing startup (we're being recognized as the fastest-growing AI startup in Chicago!)

What You'll Do.

- Sales Cycle Ownership: Fully manage the sales cycle from prospecting to closing, driving revenue growth and building relationships with key decision-makers at target companies.
- Tailored Sales Strategies: Develop and execute customized sales strategies that address the specific needs and pain points of potential customers.
- New Business Generation: Identify and actively pursue new opportunities through outreach, networking, and creative lead generation strategies
- Collaborative Partnership: Work closely with the CEO and other team members to iterate on sales approaches, messaging, and market feedback, directly influencing product and market strategy.
- Lead Expansion in an Open Market: Take advantage of a greenfield opportunity to penetrate an underserved market, driving significant top-of-funnel activity and converting early adopters.

## Qualifications for the Role

- 3+ years of experience in SaaS sales or related fields
- Experience selling global enterprise sales or enablement solutions is a strong plus
- Proven track record of exceeding sales quotas and driving revenue growth
- Ability to manage the complete sales cycle with a strategic approach
- Strong interpersonal and communication skills with the grit to “figure things out” on the fly
- Independent, proactive, and comfortable in a fast-paced, ambiguous startup environment
- Ready to wear multiple hats and take on additional responsibilities as the company grow

## How We Operate

At Letter AI, we operate by a set of core principles:

- 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)

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