---
title: 'SDR Manager at Letter AI'
canonical: 'https://feeny.ai/job/sdr-manager-letter-ai-chicago-596ke1yh6mkm'
type: 'job'
last_seen: '2026-10-16'
---

# SDR Manager at Letter AI

- **Company:** Letter AI
- **Location:** Chicago, IL
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-10-10
- **Last confirmed live:** 2026-10-16
- **Apply:** https://jobs.gem.com/letter-ai/am9icG9zdDrb1e70lv2xYo5V2RjoyUpk

## Job description

## About Letter AI

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 in Chicago to join us on the adventure 📈.

## The Role

As our first SDR Manager at Letter AI, you will play a pivotal role in building, scaling, and leading our Sales Development function from the ground up. You will directly manage and grow a team of high-performing SDRs, establishing the outbound strategies, playbooks, and metrics that fuel our top-of-funnel pipeline. Working closely with leadership and marketing, you’ll have complete autonomy to shape our outbound engine in a rapidly growing market, significantly impacting the company's revenue trajectory and your own career growth. Why Join?

- Exponential Growth Potential: Be part of an early-stage startup in a transformational space, where you get to build a core team from scratch and directly drive company expansion.
- Autonomy & Impact: Enjoy the freedom to make key decisions, design outbound playbooks, test cutting-edge prospecting tech, and truly own the SDR function.
- AI-Powered Platform: Work at the forefront of AI technology, leveraging our own unified revenue acceleration platform to give your team an unfair advantage.
- Build from the Ground Up: This is a rare opportunity to lay the foundations of our SDR organization, shaping GTM strategy for a fast-growing startup (we're being recognized as the fastest-growing AI startup in Chicago!).

## What You'll Do

- Team Building & Leadership: Recruit, hire, onboard, and coach our founding team of SDRs, establishing a culture of high performance, accountability, and continuous learning.
- Outbound Strategy & Execution: Design, test, and iterate on outbound prospecting playbooks, multi-channel sequences, messaging, and account prioritization strategies.
- Pipeline Generation: Drive consistent qualified lead flow and meeting creation to meet or exceed monthly and quarterly sales pipeline goals.
- Cross-Functional Alignment: Collaborate closely with Account Executives, Marketing, and Revenue Operations to refine lead handoffs, target account lists, and messaging resonance.
- Data & Performance Management: Track and analyze key SDR performance metrics (activity levels, conversion rates, pipeline quality), using data to optimize performance and report on pipeline health to leadership.

## Qualifications for the Role

- 3+ years of total experience in SaaS sales/sales development, with at least 1–2+ years of direct experience managing, leading, or mentoring SDRs/BDRs.
- Proven track record of exceeding outbound pipeline quotas as both an individual contributor and team leader.
- Deep understanding of modern outbound sales tech stacks, sequence orchestration, multi-channel prospecting, and data-driven pipeline management.
- Strong coaching and mentoring abilities, with a passion for helping early-career tech sales professionals grow and advance.
- High adaptability, grit, and comfort operating in a fast-paced, ambiguous startup environment.
- Strong communication, analytical, and problem-solving skills with a proactive, "figure it out" mentality.

## 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 What’s in it for you?
- 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

- [Recruiter](https://feeny.ai/job/recruiter-letter-ai-chicago-cqqqb084v477) — Chicago, IL
- [Customer Marketing & Community Manager](https://feeny.ai/job/customer-marketing-community-manager-letter-ai-chicago-yaggms7mmr65) — Chicago, IL
- [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
- [Support Engineer](https://feeny.ai/job/support-engineer-letter-ai-chicago-3bqqsd0j103c) — Chicago, IL
- [Enterprise Account Executive](https://feeny.ai/job/enterprise-account-executive-letter-ai-chicago-rpmeqj8feyfm) — Chicago, IL
- [Growth Account Executive](https://feeny.ai/job/growth-account-executive-letter-ai-chicago-vzt0z9hzjp1f) — Chicago, IL
- [Customer Success Manager](https://feeny.ai/job/customer-success-manager-letter-ai-chicago-vs1s7ym0a1fm) — Chicago, IL
- [Full Stack Engineer](https://feeny.ai/job/full-stack-engineer-letter-ai-san-francisco-57w0y0e9ccvn) — San Francisco, CA