Account Executive

Enboarder; Chicago (IL); On-site; USD 90,000 - 130,000; Full time

Job summary

Letter AI is hiring a founding Account Executive to drive revenue growth with full ownership of the sales cycle, from identifying leads to closing deals.

You will work with complete autonomy in a rapidly growing market, shaping the GTM function and building sales strategies. This is a rare chance to influence the company’s trajectory while advancing your career in an AI-driven startup.

Qualifications

• 3+ 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 startup environment.
• Ready to wear multiple hats and take on additional responsibilities as the company grows.

Responsibilities

• 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.

Skills

SaaS sales

Global enterprise sales

Quota achievement

Sales cycle management

Strong communication

Startup environment

Multi-hat roles

Job description

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've raised $2.7M in seed funding from top-tier VC firms, including Y Combinator, Formus Capital, Soma, Pioneer Fund, and TechNexus. We are now scaling to $1M+ ARR and looking for a founding team to join us on the adventure.

The Role

As a Founding 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.

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

• 3+ 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

• 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!