Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Sales Development Representative

Letter AI

Sales Development Representative

Sales Development Representative (SDR) Chicago Go-To-Market 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 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.

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

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!

Letter AI
Vacancy posted 23 hours ago
Similar jobs that could be interesting for youBased on the Sales Development Representative in Chicago, IL vacancy
  •  ...Sales & Business Development Representative Full-time Specializing in web development, StickOutSocial builds unique, user‑centric digital experiences combining design and strategy to tell a brand’s story. We pride ourselves on our work and are honored to be listed as a... 
    Suggested
    Full time
    Local area

    StickOutSocial

    Chicago, IL
    1 day ago
  •  ...Role Overview We are seeking a motivated and dynamic Inside Sales Representative to join our team. The ISR will play a crucial role in...  ...is ideal for individuals with a keen interest in business development and the ability to work independently as well as collaboratively... 
    Suggested
    Full time
    Immediate start

    Northwestern Mutual - Greater Chicago

    Chicago, IL
    more than 2 months ago
  • $75k - $135k

     ...proudly headquartered in Chicago, IL. Learn more at [coinflow.cash]( Role Overview: Coinflow is seeking a driven Sales Development Representative (SDR) to support revenue growth by generating qualified sales meetings through outbound prospecting. This role is... 
    Suggested
    Full time
    Worldwide
    Flexible hours

    Coinflow

    Chicago, IL
    11 days ago
  • $55k

     ...should be something employees love and look forward to every day. Who We Are Looking For: Fooda is looking to add a Sales Development Representatives that will be based out of our Chicago office.   This is an awesome opportunity to work with all areas of Fooda’s... 
    Suggested
    Full time
    Work experience placement
    Work at office
    Local area
    Immediate start
    Flexible hours

    Fooda

    Chicago, IL
    a month ago
  •  ...Founding Sales Partner (Commission Only) About Orqestrix Most growing businesses don't have a software problem....  ...You may be a fit if you have experience as: B2B sales representative Business development representative Account executive Operations consultant... 
    Suggested
    Temporary work

    Orqestrix

    Chicago, IL
    more than 2 months ago
  •  ...Sales Development Representative At Cision, we believe in empowering every individual to make an impact. Here, your voice is heard, your ideas are valued, and your unique perspective fuels our collective success. As part of our global team, you'll thrive in an environment... 
    Flexible hours

    Brandwatch

    Chicago, IL
    23 hours ago
  • $52.5k - $87.5k

     ...Sales Development Representative The Sales Development Representative (SDR) for TransUnion's Diversified Markets segment drives qualified pipeline growth by identifying, engaging, and nurturing senior-level decision-makers across a broad range of industries through... 
    Full time
    Temporary work
    Work experience placement
    Remote work
    Flexible hours

    TransUnion

    Chicago, IL
    23 hours ago
  • $23.4 - $31.95 per hour

     ...Sales Development Representative The Sales Development Representative (SDR) will make outbound calls to potential clients who have expressed interest in learning more about Docusign or appear to be strong potential customers based upon our general market focus. The... 
    Permanent employment
    Full time
    Work at office
    Local area
    Remote work
    2 days per week

    DocuSign

    Chicago, IL
    2 days ago
  • $60k - $80k

     ...Lead Development And Engagement Are you a former teacher with business experience looking...  ...role that is a true partner to our field sales team, focused on engaging school...  ...recruitment scams in which fraudsters pretend to represent our company by utilizing the name, image... 
    Remote work
    Flexible hours

    Goalbook

    Chicago, IL
    23 hours ago
  • $33.51 - $41.86 per hour

     ...Sales Development Representative Chicago, Illinois Fin is the AI Customer Agent company on a mission to help businesses provide perfect customer experiences. Our AI Agent Fin is the highest-performing AI Customer Agent on the market today, enabling businesses... 
    Hourly pay
    Full time
    Work experience placement
    Work at office
    Local area
    Work from home
    Flexible hours
    3 days per week

    Intercom

    Chicago, IL
    1 day ago
  • $53k - $55k

     ...Sales Development Representative Loadsmart is a growth-stage technology company valued at over $1 billion (a Tech Unicorn)! Our Digital Sales team is growing! We are seeking a passionate Sales Development Representative to support outbound motions for ShipperGuide... 
    Full time
    Visa sponsorship
    Work visa

    Loadsmart

    Chicago, IL
    14 hours ago
  • $20k

     ...Ready to be a Titan? ProProduct Development Representatives are crucial team members who identify and connect with existing ServiceTitan customers...  ...you are set up for a successful, long-term career in Sales. Culture of Excellence: Join a team where continuous learning... 
    Hourly pay
    Minimum wage
    Work at office
    Local area
    Flexible hours
    2 days per week
    1 day per week

    ServiceTitan

    Chicago, IL
    4 days ago
  • $72k - $95k

     ...build your career. About the Role Our Sales organization drives growth by introducing...  ...is continuing to scale a world-class Sales Development Team to help expand our customer portfolio. Sales Development Representatives are responsible for sourcing, qualifying, and... 

    BrightEdge

    Chicago, IL
    14 hours ago
  • $65k

     ...Sales Development Representative At Cleo, we are not only passionate about helping our customers reach success, but we are also passionate about our team members. We foster innovation in a thriving, high-velocity work environment. Our team members are among the best... 
    Local area
    Flexible hours

    Cleo

    Chicago, IL
    4 days ago
  • $66k - $94k

     ...Sales Development Representative This role will be based in San Francisco, New York or Chicago and is not eligible for sponsorship. At LinkedIn, our approach to flexible work is centered on trust and optimized for culture, connection, clarity, and the evolving needs... 
    For contractors
    Flexible hours

    LinkedIn

    Chicago, IL
    1 day ago
  • $20k

     ...Sales Development Representative (SDR) Are you hungry to break into tech sales and become a top performer? Do you thrive in a fast-paced environment where you can learn, grow, and make a real impact? If so, this is the opportunity for you! As a Sales Development Representative... 
    Hourly pay
    Minimum wage
    Work at office
    Local area
    Flexible hours
    2 days per week
    1 day per week

    ServiceTitan

    Chicago, IL
    23 hours ago
  • $90.3k

     ...Sales Development Representative (SDR) Chicago, U.S. (Hybrid) Webflow is the agentic web marketing platform for modern marketing teams, helping organizations build, manage, and optimize high-performing web experiences that drive predictable growth and strengthen brand... 
    Permanent employment
    Full time
    Temporary work
    Fixed term contract
    Work at office
    Flexible hours
    3 days per week

    Webflow

    Chicago, IL
    2 days ago
  • $48k - $52k

     ...Sales Development Representative The Sales Development Representative is a key contributor in a rapid growth company while representing a product suite that makes an impact on people's lives. Motorola Solutions is a global leader in public safety and enterprise security... 
    Relocation

    Motorola Solutions

    Chicago, IL
    14 hours ago
  • $54.9k - $97.87k

     ...Sales Development Representative Individual(s) must be legally authorized to work in the United States without the need for immigration support or sponsorship from Milliman now or in the future. Company Overview: Leading with our core values of Quality, Integrity... 
    Full time
    Temporary work
    Work experience placement
    Remote work
    Flexible hours

    Milliman

    Chicago, IL
    1 day ago
  • $80k - $90k

     ...Sales Development Representative (SDR) Horizon3 is a fast-growing, cybersecurity company dedicated to the mission of enabling organizations to proactively find and fix, and verify exploitable attack vectors before criminals exploit them. Our flagship product, the NodeZeroTM... 
    Work experience placement
    Work at office
    Flexible hours

    Horizon3.ai

    Chicago, IL
    4 days ago
  •  ...Sales Development Representative Please note we are actively hiring for our 2026 cohort to start in April. To be considered for hiring classes within this cohort, please submit your application by March 15, 2026. Note: This role is an in-office position, based in... 
    Work at office
    3 days per week

    Stripe

    Chicago, IL
    3 days ago
  •  ...hardworking builders and scalers to join us on our journey to create a better future of work with AI. About the Role As a sales development representative at Writer, you'll be on the front lines of the enterprise AI revolution - the very first conversation many Fortune 500... 
    Full time
    Work at office
    Local area
    Flexible hours

    Writer

    Chicago, IL
    1 day ago
  • $20k

     ...Associate Strategic Development Manager (SDM) As an Associate SDM, you'll be part of a purpose-driven team providing a game-changing product...  ...quota and conversion metrics per company standards. Sales Cycle Support: Act as a support contact for prospects throughout... 
    Hourly pay
    Minimum wage
    Work at office
    Flexible hours
    2 days per week
    1 day per week

    ServiceTitan

    Chicago, IL
    23 hours ago
  • $72.5k

     ...Sales Development Representative Sprout Social is looking to hire a Sales Development Representative for the Sales & Customer Experience team. The Sales and Customer Experience team shapes how Sprout powers the future of customer connection for today's most innovative... 
    16 hours
    Contract work
    For contractors
    Internship
    Work at office
    Local area
    Work from home
    Home office
    Flexible hours
    Shift work
    3 days per week

    Sprout Social

    Chicago, IL
    4 days ago
  • $60k

     ...Sales Development Representative (SDR) at Rundoo As an SDR at Rundoo, you'll own the top of our funnel, running outbound calls and emails to independent paint, hardware, and farm & feed stores across the country, booking qualified demos, and creating the pipeline that... 
    Casual work
    Work at office
    Remote work

    Rundoo

    Chicago, IL
    4 days ago
  • $13 per hour

     ...to cold-call, this role is not a fit for you. Own your data: every touch logged, every meeting handed off clean Learn the full sale by sitting next to it, with a defined path to a closing AE role in 1218 months Work closely with experienced AEs and Cogram's... 

    Cogram

    Chicago, IL
    4 days ago
  • $60.2k - $111.8k

     ...mid-market segment is a major growth engine for North America, representing small-to-medium enterprises with active travel spend and...  ...territory of SME and mid-market accounts. You'll partner with sales counterparts to identify opportunities and convert conversations... 
    Immediate start
    Flexible hours

    Egencia

    Chicago, IL
    3 days ago
  • $55k - $65k

     ...Sales Development Representative OpenGov is the leader in AI and ERP solutions for local and state governments in the U.S. More than 2,000 cities, counties, state agencies, school districts, and special districts rely on the OpenGov Public Service Platform to operate... 
    Contract work
    Internship
    Work at office
    Local area
    Flexible hours

    OpenGov

    Chicago, IL
    2 days ago
  • $50k

     ...mission. Our vision is to be the world's most effective virtual sales workforcea place where high-performing remote SDRs, program...  ...experience, and location, PLUS commission. Opportunities for development and advancement: Our SDR role serves as a pivotal stepping... 
    Remote job
    Base plus commission
    Permanent employment
    Local area
    Work from home
    Home office

    The Pipeline Group

    Chicago, IL
    14 hours ago
  • $27.88 - $29.33 per hour

     ...Sales Development Representative II, Local Independent Grocery - Chicago Chicago, IL We're transforming the grocery industry At Instacart, we invite the world to share love through food because we believe everyone should have access to the food they love and... 
    Permanent employment
    Work at office
    Local area
    Remote work
    Flexible hours

    Instacart

    Chicago, IL
    2 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Sales Development Representative. Be the first to apply!