The Role
In this role, you'll build the sales pipeline, generate interest, qualify leads, and book meetings for sales success while collaborating with the sales and marketing teams.
Summary Generated by Built In
Sales Development Representative (SDR)
Chicago
Go-To-Market
Hybrid
Full-time
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 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 📈.
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.
- 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.
- 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
- 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!
Skills Required
- 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
Letter.AI Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Letter.AI and has not been reviewed or approved by Letter.AI.
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Equity Value & Accessibility — Job listings for early roles emphasize meaningful or significant equity alongside salary, indicating ownership is a core part of total compensation. References to early‑employee equity ranges suggest equity participation is accessible at foundational and senior levels.
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Retirement Support — A People/Operations role description includes administering benefits programs such as retirement and 401(k), indicating a retirement plan is in place. The presence of a 401(k) points to baseline retirement coverage rather than an ad‑hoc arrangement.
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The Company
What We Do
Letter AI is the world's first generative AI powered revenue enablement platform. Build and maintain all the collateral and training you need 10x faster with generative AI. Personalize instantly by vertical or individual customers using existing data. Ask questions in real-time to your own co-pilot with expertise in your data. Scale coaching with AI simulations, including screen sharing for demo practice. Supercharge your enablement efforts with Letter AI's unified revenue enablement platform. Reach out today to learn more.
