Sales Development Representative

Letter AI • Chicago, IL

19d • $60,000 - $80,000 • Onsite

About The Position

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.

Requirements

• 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

Responsibilities

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

Benefits

• $60k–$80k base salary, depending on experience, plus variable compensation
• Every full-time teammate receives Letter stock options, so you can share in the value you help create
• Comprehensive medical, dental, and vision coverage, plus a 401(k) with company match
• Company-supported commuter, connectivity, and wellness benefits, plus daily lunch in our Chicago and San Francisco offices
• Happy hours, dinners, events, and offsites with a team that genuinely enjoys spending time together
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed