The Role
Own the full enterprise SaaS sales cycle from prospecting through closing. Develop tailored sales strategies, generate new business through outreach and networking, build relationships with decision-makers, and exceed revenue quotas. Collaborate with the CEO and team to refine sales messaging, influence product strategy, and penetrate a greenfield market. The role requires autonomy, proactive execution, and comfort working in a fast-paced startup environment.
Summary Generated by Built In
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 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 Role
As 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 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
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
Skills Required
- 5+ years of experience in SaaS sales or related fields
- Experience selling global enterprise sales or enablement solutions
- 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
- Grit and ability to figure things out in ambiguous situations
- Independent and proactive work style
- Comfort working in a fast-paced startup environment
- Willingness to wear multiple hats and take on additional responsibilities
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.
