Sales Development Representative

Enboarder; Chicago (IL); Hybrid; USD 52,000 - 75,000; Full time

Job summary

Letter AI is seeking a Founding Sales Development Representative (SDR) in Chicago to build our sales pipeline, generate interest, and create opportunities for the sales team. You will work closely with the founders and founding sales & marketing lead to engage prospects, qualify leads, and book meetings that set up the sales cycle for success.

This role offers autonomy to craft outreach strategies, contribute to our growth, and shape the sales development process in a fast-paced, AI-powered

Qualifications

• 1–2 years of sales development, lead generation, or business development experience, ideally in SaaS or tech.
• Proven success in outbound sales activities and a track record of meeting or exceeding targets.
• Strong communication skills across multiple channels.

Responsibilities

• Identify and research target accounts and engage prospects to create demand for Letter AI’s solutions.
• Qualify leads and determine ICP fit in collaboration with the sales team.
• Book qualified meetings for Account Executives to maintain a steady pipeline.

Skills

Lead generation

Prospect qualification

Appointment setting

Communication

Time management

CRM tools

Tools

CRM software

Job description

Sales Development Representative – Chicago, Hybrid, Full‑time

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, RingCentral, Plaid and Novo Nordisk 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've raised over $15M across Seed and Series A funding from top‑tier VC firms, including Y Combinator, Lightbank, Stage2 (Mark Roberge is on our board), Formus Capital, Soma, Pioneer Fund and TechNexus. 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 a Founding Sales Development Representative (SDR) at Letter AI, you will be instrumental in building our sales pipeline, generating interest, and creating opportunities for the sales team. You will work closely with the founders and founding sales & marketing lead to engage prospects, qualify leads, and book meetings that set up the sales cycle for success. This is a unique opportunity to make a direct impact, helping to shape the sales development process and play a foundational role in Letter AI’s growth.

Why Join?

• Growth Potential: Be part of an early‑stage company in a high‑growth AI space, where your contributions can shape the future of the organization and accelerate your career.
• Autonomy & Impact: Operate with autonomy to build relationships, craft sales strategies, and directly influence the company’s revenue goals.
• Excitement of AI: Engage with innovative AI technology and help transform how sales teams operate using tools like AI Sales Rooms and generative AI‑powered coaching.
• Build from the Ground Up: Play a key role in developing our account management process and executing strategies that will influence our growth for years to come.

What You’ll Do

• Lead Generation: Identify and research target accounts, engage prospects through outreach channels like email, calls, and social media, and create demand for Letter AI’s solutions.
• Prospect Qualification: Work with the sales team to qualify leads and determine which prospects fit our Ideal Customer Profile (ICP).
• Appointment Setting: Book qualified meetings for Account Executives, ensuring they have a steady pipeline to drive revenue.
• Personalized Outreach: Develop and execute outreach strategies tailored to each prospect’s unique pain points, ensuring each touchpoint adds value.
• Cross‑Functional Collaboration: Work closely with marketing on campaigns, share insights from prospects, and help refine messaging to resonate with our ICP.
• Track & Analyze: Use CRM tools to keep detailed records of prospect interactions, analyze engagement, and provide insights to refine the sales strategy.

Qualifications for the Role

• 1‑2 years of experience in sales development, lead generation, or business development, ideally in SaaS or tech.
• Proven success in outbound sales activities and a track record of meeting or exceeding targets.
• Strong communication skills and the ability to engage prospects over multiple channels.
• Extremely self‑motivated, with excellent organizational and time‑management abilities.
• A problem‑solver with a curiosity about customers’ needs and a willingness to tailor outreach accordingly.
• Comfortable in a startup environment, able to thrive in a fast‑paced, constantly evolving atmosphere.

How We Operate

• 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!