Sales Development Representative Job Chicago area,Illinois USA,Sales

View all jobs Sales Development Representative Chicago Sales Hybrid Full-time About Letter AI Letter AI is the world’s first revenue enablement platform powered natively by AI. We’re reimagining the end-to-end revenue journey by turning real customer conversations and account data into actionable insights, personalized coaching, meeting prep, and next steps. Revenue teams aren’t asking for more content or tools. They’re asking for better outcomes.

Letter does just that, empowering them to learn faster, sell smarter, and win more. We recently raised a $40M Series B and are already helping leading companies like Adobe, Lenovo, and Figma transform how their teams work. We 10xed our revenue last year and are looking for the best of the best in Chicago to help us build on that momentum.

The Role
As a 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 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
D…