Enterprise Account Executive in Chicago, Illinois at Letter AI

About Letter AILetter AI is the world's first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Adobe, Lenovo, and Figma 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 RoleAs an Account Executive at Letter AI, you will play a key role in driving our revenue growth. This is an opportunity to take full ownership of the sales cycle—from identifying leads to closing deals. You’ll be working with complete autonomy in a rapidly growing market, significantly impacting the company's growth and your own career development. The freedom to build, experiment, and create your own sales strategies will be unparalleled, as you help shape the go-to-market (GTM) function in a dynamic AI-driven startup.
Why Join?

• Exponential Growth Potential: Be part of an early-stage startup in a transformational space, where there’s massive opportunity for expansion and your contributions can significantly influence the company's trajectory.
• Autonomy & Impact: You’ll have the freedom to make key decisions, experiment with new approaches, and truly own your role.
• AI-Powered Platform: Work at the forefront of AI technology, helping sales teams deliver real impact with AI (see our work with Lenovo and Redpanda).
• Build from the Ground Up: This is a rare opportunity to be part of something bigger, crafting and shaping the GTM function for a fast-growing startup (we're being recognized as the fastest-growing AI startup in Chicago!)

What You'll Do.

• Sales Cycle Ownership: Fully manage the sales cycle from prospecting to closing, driving revenue growth and building relationships with key decision-makers at target companies.
• Tailored Sales Strategies: Develop and execute customized sales strategies that address the specific needs and pain points of potential customers.
• New Business Generation: Identify and actively pursue new opportunities through outreach, networking, and creative lead generation strategies
• Collaborative Partnership: Work closely with the CEO and other team members to iterate on sales approaches, messaging, and market feedback, directly influencing product and market strategy.
• Lead Expansion in an Open Market: Take advantage of a greenfield opportunity to penetrate an underserved market, driving significant top-of-funnel activity and converting early adopters.

Qualifications for the Role

• 5+ years of experience in SaaS sales or related fields
• Experience selling global enterprise sales or enablement solutions is a strong plus
• Proven track record of exceeding sales quotas and driving revenue growth
• Ability to manage the complete sales cycle with a strategic approach
• Strong interpersonal and communication skills with the grit to “figure things out” on the fly
• Independent, proactive, and comfortable in a fast-paced, ambiguous startup environment
• Ready to wear multiple hats and take on additional responsibilities as the company grow

How We OperateAt 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

What’s in it for you?

• Compensation: $130k–$160k base salary, depending on experience, expertise, and expected impact, plus variable compensation
• Ownership: Every full-time teammate receives Letter stock options, so you can share in the value you help create
• Benefits that have you covered: Comprehensive medical, dental, and vision coverage, plus a 401(k) with company match
• Benefits for the everyday: Company-supported commuter, connectivity, and wellness benefits, plus daily lunch in our Chicago and San Francisco offices
• Team events: Happy hours, dinners, events, and offsites with a team that genuinely enjoys spending time together
• Build with us: 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